Clueless

[Iris The Butterfly]

I have a male friend that I've known for about 5 years. Within the past year or so we've been spending more and more time together since he moved back to my city. He is the brother of one of my best girlfriends. He's 3 years younger than me (we're in our early 30s) and we have spent a lot of time over the years in a group setting with mutual friends, but more recently with his sister and her boyfriend on 'double dates' which aren't really dates between us. Lately it feels like it could be, though. I'm clueless and need some reading between the lines.

 

I really really like him and have recently gone through heartbreak and I find myself drawn to him, because I find haim so trustworthy, genuine and just an all around good guy that I get along with and love as a person.

 

We've had MANY opportunities over the years, but he's never made a move and neither have I because I'm too shy and never had to make a move on a man. When we met I had a crush but he didn't seem to reciprocate so I let it drop and have just enjoyed the friendship.

 

I've never seen him date and his sister said he's never brought a girlfriend around to meet the family or the friends. He let on recently to me that he's never fallen in love, and has had short term relationships and flings only. He's such a great guy, everyone is surprised that he's single and my female friends have commented they're surprised we're not dating each other because we should. His sister stays mum. But recently she snapped a pic of the two of us and sent to me. She said when helping me mend my broken heart to not forget what a catch I am, she sees it, her brother sees it.

 

I was dating someone for 5 months earlier this year and he met him several times and they seemed to get along really well. The heartbreaker said once after we were all hanging out and we were alone: "He's in love with you. I can tell by the way he talks about you and the sparkle in his eyes when you're around." I was surprised.... and I couldn't help the smile from breaking across my face. Still, I said, "no, no, you have nothing to worry about, we're just friends!" But when that guy left me in the ditch, I began to wonder if he saw something that I didn't. Men who like a woman and want her to themselves wouldn't even notice another man being interested and perceive it as a threat.. unless there was truth in it. Right?!

 

Sometimes the friend would ask about the heartbreaker, while I was dating him and asked how things were going. I figured he was just being friendly. In the past 6 months or so, his contact increased to a couple times a week. He happened to move into my same office building so we run into each other sometimes downtown. We text each other during the week about coffee spots, happy hour locations, building events and drama, etc. He initiates about half the time, seemed like a little more when I was dating the other guy. Funny how that is, isn't it.

 

Coincidentally, he is now not only my friend but my realtor. We have gone to see a couple open houses over the past month that he's arranged. He picks me up at home, drives around, and usually we will get a drink after, sometimes dinner and make an evening of it. Sometimes alone, sometimes with our friends or his sister. When he moved back to my city in November 2017 I was still dating the other guy, but one night the friend invited me over to see the new place and I brought over a little wine as a housewarming gift. I had told the guy that I couldn't see him that night because I was bringing a friend a housewarming gift and he was clearly jealous. In my mind, he was (and is) still just a friend.

 

Once, in the past couple months, he asked me to dinner and he insisted on picking up the tab. For the very first time he complimented me, saying that I was "pretty" and "nice". He's never complimented my appearance or personality before. Not long before that we had met for drinks after work and we both had a heart to heart. He opened up and so did I. I told him all about my breakup and being dumped by someone I thought was so into me. It was interesting to hear his insight and a man's point of view. It was the first time we really opened up on a deeper level like that. That's been happening more lately. Sometimes he's asked over the months if I'm dating or inquires about specific men, like my exes or if I'm going on a date. Once I complained about the heartbreaker and a mean thing he said to me once. The friend said, "he's a dumb!@#"

 

Over the past week, I've noticed he's getting more close to me and... maybe more protective and caring than before. I have a couple guy friends who would rush to defend me and care about my safety and happiness so I don't know if he's just being a gentleman or really cares about me in a romantic way. We had a scare in our office building a couple weeks ago and he warned me of what was going on and waited for me outside and I ran to him flustered and upset. He took charge and told me to drive home safely and to meet him back at home and we would get a drink. I've noticed (maybe because I'm finally paying attention) that he always positions himself next to me seated at a table with other people. He sits near me whenever possible. He walks me right to my car door. It's not uncommon for us as friends in the group to pick up the tab for a round of drinks, etc. But I've noticed he's been more generous with me lately. I confided in him about something that's been bothering me and he's been extremely supportive and caring and encouraging. The other night for the first time, he kissed me on the cheek. I couldn't tell if it was brotherly, friendly, or romantic. He's not a touchy guy. We usually have given each other hugs goodbye but never a kiss.

 

I'm happy enjoying our friendship and getting closer, but I don't want to assume anything romantic if there isn't. But I would really like it to develop into romantic territory. He's a catch and we have a connection. Thoughts?

Edited July 10, 2018 by littlebridge

[DenimRoad]

I am in another post getting help with what I understand is an emotional affair. But setting that aside, I read this and it reminds me a lot of being young and being friends with my now-wife. I’m a shy guy like him and was scared to make a move.

It’s very familiar because he may not be dating since he sees you as the ideal woman. Nobody else compare. I know that feeling.

What I suspect the real issue is, as it was for me, is terror over messing up the friendship. When I was in his shoes, i knew even bringing it up would make things very different. I was afraid she would feel awkward, push me away, and become a mere acquaintance as she finds a boyfriend.

He sounds like a good guy who loves you but is afraid to do anything that may scare you off.

I think that you need to have a conversation he feels safe in. If I was him, I’d love to hear you say, “I love what we have as a friendship. It feels like we’ve grown closer more recently, beyond just friends, and I really like that. You’re not going to lose me, and I promise I won’t feel awkward and things will become weird. I care too,much about you. How do you feel about us?”

[Iris The Butterfly]

Thank you so much for this! I loved hearing your point of view and your happy ending. What was the turning point and how much time did it take for YOU (or was it HER, like you're suggesting I do) to make a move?

 

I can see why he might be terrified to lose the friendship, or risk my rejection seeing that I'm so close with his sister, she and I would still be friends and obviously he's close with her and if it didn't go well it would be awkward. I guess better to not go out on a limb to preserve the friendship. But lately I find myself thinking of him more and more. I've dated a lot but he and I have a connection and we get along so well and we respect each other and have a great time together. I've thought to myself, "It's too bad we're just friends... I would totally date him!" It's so funny, it took another man who liked me to notice and point out this guy's "obvious" feelings for me. I wondered why no one ever mentioned it before, he was the only one who ever has. I'm glad he said something because I can be aloof and a little dense and wouldn't have recognized it.

 

I don' know if he thinks of me as an ideal woman and no one can compare, I'm far from perfect and maybe he does date on the sly, who knows. He never talks about other women, at least in front of me. He's handsome and a catch, he could get lots of women and I've seen women approach him while we are out in a group. I can see he's shy with women as far as making bold moves. He's friendly and sometimes flirty, with me and I've seen with other women around in the past.

 

Lately I've been hurting and it's easy to want to lean on a trusted friend and a man who gives his attention and genuinely cares for me. I wouldn't use him as a crutch, I have genuine feelings for him too. When we had that scare in my building, I know it sounds corny, but he contacted me to warn me of the danger, he didn't have to do that but he was concerned for me, and when I saw him outside of the building I was flustered and scared, he was a 'hero' for that moment and all of a sudden I felt a pang of something more than friendship when I saw him waiting for me. I wanted to run to him and I know that sounds silly and girlish, but it's true. When I saw him, we hugged and silly me, I wanted to just stay there for awhile.

 

It's really hard to put your feelings out there. Clearly I'm feeling something lately, it's always been underlying. I just never thought he liked me the same way so I dismissed it and have been involved with other men.

 

I saw him a couple days ago in a group setting and we haven't spoken since. We have already made some plans for next weekend and we will talk before then. To be honest I wish there could be more opportunities for one on one but I'm shy myself to ask, now that I'm picking up on some signals and also feeling closer to him. I feel like an idiot and don't want to totally give myself away. Like I said sometimes I can be aloof and am guilty of being oblivious to men's interest. I assume if a man isn't making bold sweeping gestures of pursuit and clearly indicating how much he likes me, then he's not interested. I know that isn't true but I can still be like a girl in that way instead of a woman in her 30s.

 

Maybe for the time being I can just enjoy the connection because it is special, and seems to be deepening. I feel comfortable with the friendship and like I said lately we've been spending more time one on one. Maybe in time it will develop to a point that I or he could feel safe about expressing what you suggested.

 

I really appreciate your advice

[preraph]

Good grief. He finally asks you to dinner and all you do is unload on him about your ex? Men HATE that. It puts them in the friendzone. Men don't want to hear about your ex and how heartbroken you are over him! This guy is already afraid to make a move and now all you've done is reinforce that all you do is think about your ex and your heartbreak. Why couldn't you have just gone out and had a lighthearted conversation that would be entertaining to someone? He's not your shrink. Men want a woman who is happy and fun. You somehow equate dumping all this on him as the way to bond with him. Just because he was decent about it doesn't mean it made him more interested in you and it probably discouraged him. Very few men want to hear you bare your soul about past guys! You've got to be fun and entertaining and just see if you can have some laughs with him. It's a date, not therapy session.

[Iris The Butterfly]

Good grief. He finally asks you to dinner and all you do is unload on him about your ex? Men HATE that. It puts them in the friendzone. Men don't want to hear about your ex and how heartbroken you are over him! This guy is already afraid to make a move and now all you've done is reinforce that all you do is think about your ex and your heartbreak. Why couldn't you have just gone out and had a lighthearted conversation that would be entertaining to someone? He's not your shrink. Men want a woman who is happy and fun. You somehow equate dumping all this on him as the way to bond with him. Just because he was decent about it doesn't mean it made him more interested in you and it probably discouraged him. Very few men want to hear you bare your soul about past guys! You've got to be fun and entertaining and just see if you can have some laughs with him. It's a date, not therapy session.

 

A little harsh. That conversation happened one time over a drink months ago. Not when he asked me to dinner. And btw, that wasn’t a date, or at least I didn’t think it was.. clueless here.

 

I “unloaded” about my heartbreak to him once over a heart to heart and he opened up to me about a personal issue. I never mentioned it again. And we had plenty of laughs and it was light otherwise.

 

I was asking by posting this thread if it seemed he was interested in me as more than a friend and advice going forward. I’m not using him as a shrink- that would be crappy. We’re friends and we both share personal things.

Edited July 11, 2018 by littlebridge

[Versacehottie]

I like it

 

It all sounds like a very promising beginning. I have several couple friends who got together like this. Hanging out in a group and everyone else would comment on the fact that there was a spark between them (a few of them even denied it but ended up together like the most natural thing in the world). Sometimes your friends can notice before you are even aware (or see that you would be great together). I agree with the post that describes how you should approach the conversation. While I'm sure it would be scary to say, I think it allows him to give any answer comfortable without messing up the friendship. Which btw i also think he likes you as more than a friend, so is probably wait for a green light from you. Good luck

[Iris The Butterfly]

Thanks Versace!

Other than saying that, in the meantime I would like more opportunities to have one on one time with him Because I couldn’t have that conversation at all if we weren’t alone. I’m so terrified of rejection myself right now it’s hard for me to put myself out there. Sometimes it’s easier to just see him as part of the group setting, rather than reach out and initiate. Sometimes I do though, I guess lately now that I realized I like him as more than a friend I feel a little shy and self conscious about showing my romantic interest.

Edited July 11, 2018 by littlebridge

[Versacehottie]

Thanks Versace!

Other than saying that, in the meantime I would like more opportunities to have one on one time with him Because I couldn’t have that conversation at all if we weren’t alone. I’m so terrified of rejection myself right now it’s hard for me to put myself out there. Sometimes it’s easier to just see him as part of the group setting, rather than reach out and initiate. Sometimes I do though, I guess lately now that I realized I like him as more than a friend I feel a little shy and self conscious about showing my romantic interest.

 

You're welcome. You just need to find the little inside jokes or things that are for just the two of you. Like let's say you like a certain activity that your other friends wouldn't be very interested in or not able to go. Then you build on those times, texting or calling in between and being a little flirtatious or playful. If he hasn't wondered already (pretty sure he has), then he will be more sure that he has a chance and what he is feeling is mutual.

 

One of my friends that is one of the ones that I referenced in the my post to you is really into music and concerts. So is her now guy, who started as her friend (she knew through work) and would come out in groups with us. Because they had same taste in music, and she always was getting tickets & going several times a week to concerts (and he did too), it became something they did together but separate from the group. Probably did not take much more than a couple of times of her saying let's go to this show, until it was their "thing" together. She was able to ask him because they really had that in common & most of her girlfriends (i.e. me & others) were either busy or didn't care nearly as much about this or that particular show. Helped by the fact that tickets were often last minute and quantity 2! They were "friends" for real for about 1 year but did tons together and also came out with the group, and all of us were noticing they should be together during that time. She didn't start this to try to turn him into her bf though that is what eventually happened. I can think of other examples but that's a good one.

 

So what is something in common with your guy that you can use? It can even start with something smaller, like inside jokes. You need something that you can get some traction on and have a relationship "away from the group". If you tell me a little something about what your connection with him is, I'm pretty good at figuring out a little entry point. Ok, think about it.

[DenimRoad]

I’m happy if I can offer any help. We were best friends in the last couple years of college and spent tons and tons of time together as great pals. She was dating someone who really wasn’t good for her. I guess i compensated for what he wasn’t providing. As a friend, I’d occasionally point out where he just wasn’t good for her. Senior year I realized she was really the woman for me. I found it impossible to date because I’d always compare and rather spend time with her. As graduation was getting closer, I was more direct about him. She led him to believe i was gay to keep,him from being jealous. A couple months into summer, without me around, she saw more of what I was seeing in her guy. We would always be talking and she finally broke up with him. I hung up the phone and cried and cried with relief. A month or two later I asked what she was going to do next with dating. She said she needed some time off. We were spending more and more time together. One day we just started holding hands in the car while I was driving. Nobody said anything. It may have happened a couple times again. It felt right. Then one of us said this feels right. We transitioned to dating, which wasn’t much different from what we were doing for the last couple of years except that we could kiss. Maybe a year later I proposed, which she was well aware was coming. A year later married.

 

So two years as best friends at school spending the majority of every day together. A year dating. A year engaged.

 

Your story is so very familiar. I was horrified of putting it all on the line and potentially losing my best friend. I got to the point where it was a matter of a) you only live once, b) if I’m misreading this I must be insane, c) I’m torturing myself by yearning for her and can’t keep doing this, and d) if this wasn’t going to work, I’m missing out on a lot of time that can be spent finding someone for me.

 

I felt I wasn’t good enough as well. I was the shy one. I was in awe of her. But objectively, she was spending all this time and building this great relationship with me. I wasn’t a charity case for her. She was into,me.

 

It sounds like you guys have a solid connection. That can withstand asking how he feels about you two.

 

I can only react to what you’ve written and reflect on my own experience. The one on one time is important, even if it’s phone calls. You will grow closer and get more comfortable for having that conversation. Or maybe you’ll learn he may not be a great fit for you. But you’ll have some resolution and some peace.

 

What kind of things are you considering for next weekend? Is it just you two? Is this a rare situation for you two to be hanging out?

[Iris The Butterfly]

So what is something in common with your guy that you can use? It can even start with something smaller, like inside jokes. You need something that you can get some traction on and have a relationship "away from the group". If you tell me a little something about what your connection with him is, I'm pretty good at figuring out a little entry point. Ok, think about it.

Well, in the past month or so we have a reason to talk outside of the group and spend time because he is acting as my realtor and we will talk about the listings he sends me and open houses. Like I said, twice he and I have made an afternoon/evening of it. I would use his 'favor' of picking me up and driving me around and showing me the places as a segway into, 'hey let me buy you a drink for helping me out today'. So far it's never been just a drink. More like two and dinner, hours and hours.

Today I asked him if he wanted to join me for a walk through a little festival in our town but he got tied up with work and couldn't. He's very focused on his career and building his security which is admirable and he dedicates a lot of time to that during the weekdays. He also likes to do fun things and is social and we have many similar interests. For example once he mentioned trivia night, we both like boating, live music. Actually we're both really into music. He loves going to concerts and I'm more of a small venue kind of girl but really into that. I think something that we've always bonded with is music. I love to dance, he's more of a wallflower. But we danced a couple times. I would say something related to our love of music.

 

It sounds like you guys have a solid connection. That can withstand asking how he feels about you two.

 

I can only react to what you’ve written and reflect on my own experience. The one on one time is important, even if it’s phone calls. You will grow closer and get more comfortable for having that conversation. Or maybe you’ll learn he may not be a great fit for you. But you’ll have some resolution and some peace.

 

What kind of things are you considering for next weekend? Is it just you two? Is this a rare situation for you two to be hanging out?

Thank you for sharing your story. It's a really romantic one. I like how one day you just held hands in the car. How sweet.

 

I would say we definitely have a solid connection but I wouldn't go so far as to say we are best friends like you were with your wife before you became involved romantically. Like I said we mostly have spent time in the group until maybe about 6 months ago when he moved back closer to my city, and then working in the same building, we've just had more of an opportunity to spend time one on one, and as I've mentioned about the open houses, and going to dinner, having a drink after work. I would say the alone time has increased just in the past 2-3 months... once the other guy dropped out of the picture. While I was dating him, the friend and I would communicate fairly regularly but never spend time alone.... well, once when I came by to see his new place.

But it's more common that we are in a small group setting, however, lately before or after being in the group we have been spending time alone. For example, last week for the 4th of July, he asked me to meet him at his place and we walked together to meet the other friends for lunch. And before that after dinner with him and his sister, I stayed for a bit after talking with him. You get the idea.

 

I've known him for about 5 years, not as well as I've gotten to know him just in the past year, so I've had a chance to observe him in many ways. I don't consider him painfully shy, just maybe shy when it comes to pursuing women. I don't know if he'd be a great fit for me, but as far as I can see I think he would be. Maybe my only concern is that he's a couple years younger than me. Maybe he would prefer a younger girl? And as a woman in her 'almost mid thirties', I'm looking to settle down and have a family. He knows that about me and he's never even had a serious girlfriend. He knows I want a serious relationship and would like to be married with kids. I guess I'm not sure if he's as ready as I am to settle down is what I'm saying. He just got started in with his career and is building his empire so to speak. He's got time and I would have liked to be married with kids by now (with the right guy, because I've had the chance in my past and didn't take it a couple times). However, most of his friends and our friends are married, planning engagement, and/or and settling down. He and I are the outliers in our circle of friends. But.. we're both old souls and usually old souls have trouble really connecting on a deep level with most people, especially romantically I've found. It's like you have to have a true friendship AND romance on deep levels to really have something great, and that's SO hard to find, isn't it!??

 

For the event next weekend we've been planning to go to an annual event that's kind of big in our city. I don't want to give it away to remain anonymous... it's a day trip and consists of getting dressed up, a concert is involved, it's a little out of town. His sister and her boyfriend and possibly another friend was interested in going too. It wouldn't be a situation where we'd be alone although I wouldn't mind if we were.

 

I just started picking up on little things that he's been doing lately that indicate more than friendship which brought me to this post, and also because the guy I was dating was jealous and said he can tell he's in love with me. I didn't believe him at the time and dismissed it, but it made me finally pay more attention. Like the other day at dinner at one point he put his arm on the back of my chair. Maybe I'm reading too much into that. But that's something men usually do with a woman they're... being affectionate with. And the kiss on the cheek, and the walking me to my car, not just to the car, but right to the door. He walked me to my Lyft opened the door for me saw me into the car... etc. I mean, I have male friends but they don't do those things.

 

So, since I asked him tonight to meet if he was free and he couldn't, I'm actually busy and have a date on Saturday... I met someone online and this will be our second date. I'm interested in getting to know my date but I still want to spend time with my friend of interest. I'm busy with friends and the date for the next couple days, and I probably won't see him this weekend. But.. we have plenty of reasons to keep in touch and next weekend will be for sure.

 

I'm actually ok with just letting things happen as they will naturally. Maybe there will be a good time for me to bring up that conversation, or at least find more common activities we can do away from the group. Who knows, we may end up just being really good friends for the rest of our lives. In the meantime, I'm single and so is he, and it's been really nice to spend time one on one lately, and I'm looking forward to more of that.

[Versacehottie]

Well, in the past month or so we have a reason to talk outside of the group and spend time because he is acting as my realtor and we will talk about the listings he sends me and open houses. Like I said, twice he and I have made an afternoon/evening of it. I would use his 'favor' of picking me up and driving me around and showing me the places as a segway into, 'hey let me buy you a drink for helping me out today'. So far it's never been just a drink. More like two and dinner, hours and hours.

Today I asked him if he wanted to join me for a walk through a little festival in our town but he got tied up with work and couldn't. He's very focused on his career and building his security which is admirable and he dedicates a lot of time to that during the weekdays. He also likes to do fun things and is social and we have many similar interests. For example once he mentioned trivia night, we both like boating, live music. Actually we're both really into music. He loves going to concerts and I'm more of a small venue kind of girl but really into that. I think something that we've always bonded with is music. I love to dance, he's more of a wallflower. But we danced a couple times. I would say something related to our love of music.

 

 

Thank you for sharing your story. It's a really romantic one. I like how one day you just held hands in the car. How sweet.

 

[]

 

Oh right I forgot about the realtor part, that an excellent thing for you guys to do separately and build upon that, especially because finding a home involves every part of life. So while you are seeing or discussing potential places, you can insert anything you would like to build on, like i'll just take gym as an example, you can say something about it being close to xyz gym or his gym or running place and say you guys should go sometime. You can also be playful with him about purposely dragging home hunting on and on so you can keep enjoying after open house drinks & dinners. That's one way to test the waters and be flirtatious with him and see what he says back. Also something that happens quite frequently in situations like yours is you guys will start to talk about very small daily things and needing opinions and help on very small things--each of you will be willing and happy and excited to take part in. So definitely make sure you do that on your end. I can help you think of examples of things you can do.

 

You want to have small reasons for contacting each other, to build on the separate relationship (not to do with group or solely the house search) to contact each other. So even taking music or a concert as an example, say he is going to one the day after he takes you out house hunting, tell him to let you know how the concert is. Sounds totally stupid but it's harmless & even though you can probably see how it was via his social media & know he's going to have fun. It's a way for him to have a reason to get in touch with you and expand on things himself and it's an easy bridge for you to say hey I saw so and so are coming next week, we should go to this next show together. It also gives you a chance to give him compliments as you get to know him better about other parts of his life etc. Haha I remember when i had some similar situation to yours and my guy texted me to ask where he could find a certain phone case--hello google? Of course i didn't mind and he knew where to find it on his own. You know stuff like that. But you take small things like a small mention of buying a new phone and build on that. It does't necessarily have to take a long time & in some ways it feels like you guys are farther along than you might realize on the surface. Those kind of clues are there to an neutral observant outsider. You can also start teasing him or planning your outfits for this weekend's event. Stuff like that. The thing that's good about all of this is you can fall back on friendly/friends if you need to because it's not outrageous that you'd be in contact with him about any of these things. Feeling scared is part of the excitement. Take a few small steps and see if he reciprocates. I'd be surprised if he didn't. Good luck

Edited July 13, 2018 by a LoveShack.org Moderator
Truncate quote

[DenimRoad]

[]

 

I'm actually ok with just letting things happen as they will naturally. Maybe there will be a good time for me to bring up that conversation, or at least find more common activities we can do away from the group. Who knows, we may end up just being really good friends for the rest of our lives. In the meantime, I'm single and so is he, and it's been really nice to spend time one on one lately, and I'm looking forward to more of that.

 

You have an amazing attitude based on your last paragraph! Some thoughts- don’t worry about the age difference. It’s so unimportant. Maybe 40 years ago it mattered, not now.

 

From what I’ve read, I’m guessing it took him a lot of guts to put his arm of the chair and kiss you. He probably thought about doing it for a long time. Seems like he’s trying to test the boundaries.

 

Other guys can be good at reading other guys. We know how we think. Someone else picking up on your friend being in love with you is probably a good read.

 

Yes, you should plan to meet up with him alone. If anything, just to build some quality memories together and get to know each other. Plan for lunch, brunch, walking around to get ice cream and see others dressed up. You guys are buddies- nothing strange about hanging out.

 

Are you telling him about your date? I’m not sure how to play it. You can keep it quiet but he may find out or you may have to say you hid it from him. You can tell him. Not sure if that would shut him down or make him double down on his efforts. Or you could mention it and use it to turn the conversation into ideal dates. You could say you doubt if the guy is good because of certain reasons, say how your friend is different, say others can see you together,etc.

 

It sounds like your biggest opportunity is to build quality moments together and learn more about each other.

 

The guy obviously likes time with you, he’s sending you signals, and he seems shy to make a move or rock the boat. I think there is something there.

Edited July 13, 2018 by a LoveShack.org Moderator
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[OneParadox]

You need to make a move. Yep, be bold. This guy will be thankful.

[Iris The Butterfly]

You need to make a move. Yep, be bold. This guy will be thankful.

 

OK.. so I've put it out there this week already inviting him to meet just one on one but he hasn't taken the bait, busy or otherwise.

He contacted me Friday asking how my day was going, Friday I had plans after work and I posted a picture on social media and he was the first to 'like' it. Today he texted asking how my weekend was going and we texted back and forth, when I eventually asked if he wanted to meet me out for a drink he said he had made dinner plans otherwise he would join me. So I'm kinda getting mixed messages here.

We talked about the plan for the event next weekend and it is becoming a group activity. We will still continue to spend time together and are in regular communication but he's not going out of the way to solidify one on one plans with me, and I have made the initiative. Yet he's contacting me.

 

I went on my second date last night with a guy I met online and I like him and am planning to see him again. I would really like to get past the friendship boundary with this guy but things aren't really moving along in the way I would like. I tried to make a move by inviting him one on one earlier this week, and today, when he was the one to reach out to me the other day and today, I took that as a good sign but nothing materialized. Seems like a stalemate at least this week. I'm going to stay quiet and not contact him and see if he comes forward in the coming days. If not I will see him this coming weekend either way.

 

I'm not used to having to make the move with men so this is difficult for me. I thought if he is interested I would just present more opportunities for one on one and judging by the way he has been acting around me lately, maybe he would be more likely and comfortable making a move himself. But that's been a fail this week anyway.

Edited July 16, 2018 by littlebridge

[OneParadox]

Ok... this is my general advice to women: your job is to make yourself sexy and irresistible in the looks dept (you don't have to be a model or have a perfect body, but do send a message you are in the market for a man). Also be flirty (in a classy, subdued kind of way) and approachable. Don't be afraid to get physically close to a guy. And, don't be afraid to send a message that you like someone. BUT: do NOT appear desperate. Just like expensive jewelry or fine perfumes, scarce goods are the most desired (obviously don't skimp on the advertising).

 

If Mr Young can't make up his mind soon then move on. And same goes with Mr OLD: if things aren't going the way you want them to go, keep moving. The right guy will show up as long as you keep putting yourself out there.

[Iris The Butterfly]

Thanks but I got that covered! I've never had a problem attracting men, my problem is I'm usually oblivious to the good guys who really care about me and instead get distracted and fall in love with the ones who make it really, really obvious that they are interested. I have trouble picking up on the subtler clues that a man likes me if he doesn't say anything or holds back.

That's why I posted this thread.

 

And p.s. nothing personal, but I just HATE it when people say, "you'll find someone" ! I always do find someone. The problem for me is that I fall in love with men who aren't in it for the long haul or who probably wouldn't be good long term partners. And the ones that would.... I don't have the same feelings or, like this guy (potentially), isn't making it clear to me that he's interested romantically.

 

Lately he's been warming up to me but still isn't making any bold moves. Earlier this past week I tried to initiate one on one but even though he had initiated texting ME, he wasn't able to or didn't want to meet up. So.... I'm sorta kinda confused here.

[Versacehottie]

OK.. so I've put it out there this week already inviting him to meet just one on one but he hasn't taken the bait, busy or otherwise.

He contacted me Friday asking how my day was going, Friday I had plans after work and I posted a picture on social media and he was the first to 'like' it. Today he texted asking how my weekend was going and we texted back and forth, when I eventually asked if he wanted to meet me out for a drink he said he had made dinner plans otherwise he would join me. So I'm kinda getting mixed messages here.

We talked about the plan for the event next weekend and it is becoming a group activity. We will still continue to spend time together and are in regular communication but he's not going out of the way to solidify one on one plans with me, and I have made the initiative. Yet he's contacting me.

 

I went on my second date last night with a guy I met online and I like him and am planning to see him again. I would really like to get past the friendship boundary with this guy but things aren't really moving along in the way I would like. I tried to make a move by inviting him one on one earlier this week, and today, when he was the one to reach out to me the other day and today, I took that as a good sign but nothing materialized. Seems like a stalemate at least this week. I'm going to stay quiet and not contact him and see if he comes forward in the coming days. If not I will see him this coming weekend either way.

 

I'm not used to having to make the move with men so this is difficult for me. I thought if he is interested I would just present more opportunities for one on one and judging by the way he has been acting around me lately, maybe he would be more likely and comfortable making a move himself. But that's been a fail this week anyway.

 

Hmmm, i'm surprised. The only thing I can think of is because it's a bit of a leap because you are friends there's no sense of urgency for him. (funny, much like my 2 music friends that I was telling you about). To be honest, most of my friends that are together with a guy that they were friends with, actually experienced this--that the guy would sometimes accept the invites and sometimes not, not really seeming like they cared. I think it both took the guy a while to realize what the invites were actually for/to see a benefit for himself in the invite AND that in most of the cases the guy wasn't quite ready-ready for a relationship. Just taking the music friends as an example, he wanted to be more secure in his job and advancing and his mom was going through severe health problems. I would think for a real estate guy, he might also feel a great need to get onto better footing with his career; often motivating and get lost in the "next deal" etc.

 

I do think that you should pull back a little but not as much as if you were actually dating. I would think even as a friend who had to decline because he already had plans, he would initiate the next ones with you alone. And i think some more flirting when you see him in a group. he could be kinda clueless that you are ACTUALLY interested. Ok let us know

[Iris The Butterfly]

Ok, so... to follow up on my last post... over the past week I think he has initiated contact with me nearly daily although we haven't seen each other for a week and a half....when I made the invitation on Sunday when he reached out, he had other plans for dinner otherwise he said he would have met me for a drink as I suggested (in response to his reaching out). But since then he has been extending and initiating the conversation almost every day.

 

Anyway, we have a fun day planned this weekend with an outing with a small group of friends. Not only have we been talking about the outing, I noticed that he has been contacting me about work events, things going on around our office building, etc. Kinda like just like meaningless stuff, an excuse to talk. I noticed that I did that myself....I was going back through the text thread and it seems like the contact really started picking up mutually in the past three months. Coincidentally, that was after we had our first real heart to heart and I told him about the breakup that was all in mid-March. While I was in the thick of it with the other guy, a couple times he would hint at or straight up vocalize the fact that he noticed the attention that this friend gave me and was maybe a little jealous towards my attention I gave to him. Often times, other people see things that we don't see ourselves. I didn't ever recognize that he was flirting or his eyes sparkled when he talked about me, but the guy I was with did. Funny how maybe a really good thing may have come out of my breakup..had he not pointed this out, I would never had paid attention and changed my view towards my friend from seeing him as more than platonically interested. I would have still enjoyed being with him and would likely want to spend time with him as I always have, but I wouldn't have started to notice that there was or could be something there. I trust that if a man who liked me saw it, than he has to be right. No one else has ever mentioned it. I'm not sure why he was the only one who's ever said it, but I'm glad he did, after all.

 

In April or May, (side story but relevant to this thread and "Friends and Lovers"), I have a male friend that I've known for the better part of 20 years profess his love for me and ask me to date him with the intention of wanting to marry me. I know, crazy. I could really write a book about my romantic relationships, I swear. This other friend is more than 15 years older than me, and although I love him and care for him and think he's a wonderful person, we have a very special relationship and truly are close friends and love each other very much.... I went out on a couple dates with him after he said that and realized that the age difference among other things was too large for me, he's over 50... and I'm in my 30s. About 5 or so years ago, we slept together once and have never had any romantic repeats since. We've always stayed friends, we both were in long term relationships since and he was even engaged in the past couple years but it broke up. I just never felt that romantic passion for him, not the way I had recently experienced with the heartbreaker, not the way I've felt with all my previous serious relationships. So I was struggling with the fact that I had a man that really loved me and wanted to commit and knows me in and out and who I trusted and respected.... but I didn't feel the romance and longing for.

 

Coincidentally, during the same time, the younger friend (the subject of this thread) started spending more time with me and we started getting closer. I was grappling with the decision and my feelings for my older friend who was clear he wanted to date me, after many many years of never making a move... and the bombshell of his desire and intention to marry me... I found myself going to see a couple open houses with this younger friend, and dinner followed, and a couple drinks... we both had other invitations.. and neither one of us wanted to go. We spent the entire afternoon and evening together. So, I knew then that if I was choosing to be with this guy over the other one, my answer was clear. During this time I was so down and heartbroken and overwhelmed with emotion... I asked for a 'sign'. I think my sign was recognizing that I have feelings for this guy and he has feelings for me. I guess it's just a matter of making it happen. The comparison of excitement and butterflies that I feel for this friend compared to how I feel about the friend who is much older... became evident. I spent time with both of them... and I realize that, no surprise... I prefer to be with a man close to my age. I've had serious boyfriends who are 10 or so years older, but over 50 at my age, just seems too much of a stretch. I still want to have kids, I'm 34 but a man in his 30s also is at the same 'level' as I am, or at least in general. It would be more likely that we both would want the same things and are in a way, on the same 'page'. I began comparing the two friends in order to sort out my feelings. This guy is young, and he we have a lot of similar interests and he is social and active and... well, close to my age... compared to the other friend who ... isn't, and who I don't have those same butterflies about seeing in a romantic capacity. Plus, he doesn't have the best health and I thought... if I marry him what if he dies in 10 years? Who's to say that would happen, but I just couldn't get past the age difference. He knew it was a factor for me, and was for him too for a long time. Sometimes I wonder if maybe I'm making a grave mistake and one day will look back and regret it, but I knew that I didn't have the butterflies that I feel for him that I do for this guy. When I went on dates with him compared to the "dates" I've been on with the younger friend....I feel that cozy togetherness and well, physical attraction. I think that sometimes you can get along and be really amazing friends but not click in a romantic capacity. I saw a potential in this, and it's been enough for me to post here about it and want to pursue further.

 

When the younger friend and I went out to dinner and he picked up the tab (I consider that seemingly like a 'date', although at the time his invitation was framed casually).. he glanced at my left hand that I put to my throat while talking, as I do sometimes in a nervous habit. He said, "So I hear you had a proposal?" I told him that the age difference was a big factor for me, and that we had known each other and been friends for many years... and that he had finally admitted his love for me, but I wasn't sure that I felt the same way and that he was much older than me and I didn't feel comfortable with that. He agreed, the age difference is a big factor. He shook his head and said, "no, don't do it." And well... I didn't. So, over the past two months he and I have become much closer than before. He's been the guy that's getting the majority of my attention. I date occasionally but nothing more than once or twice lately. So he's the guy I'm talking to regularly and seeing a couple times a week. It's almost like we could be dating, or should be, the way I see it. But... it takes two.

 

Here's my plan. When I do see him this weekend I'm going to flirt outside of my comfort zone (nothing crazy, light touching, smiling more, etc.) I'm sure that will be easy for me to do since it's natural anyway and I probably already have been flirting without my knowledge all this time. I'm not going to initiate spending time again until he does. If he wants to text me daily or every other day, he can do that, we don't necessarily have to meet. I'm just going to hang back a bit but definitely flirt more now.

Also... I'm going to continue to date other men. I had two dates over the past week and I'm online so dates seem easy to come by... and in person too, I am in demand and going to enjoy that while I can! If he doesn't make a bold move despite my flirtation and invitations, then maybe he isn't looking for a relationship or wants to cross over the boundary... and that's still ok. I would still be very happy having him in my life and getting to know each other better as we have been.

[Versacehottie]

Good plan! Let us know how it goes!!! It might take a little time and a little patience but I would be really surprised if your situation with realtor friend doesn't turn romantic (and probably serious). Good luck!

[Iris The Butterfly]

Good plan! Let us know how it goes!!! It might take a little time and a little patience but I would be really surprised if your situation with realtor friend doesn't turn romantic (and probably serious). Good luck!

 

Thanks. Time!! He said today how he can't believe we met over 5 years ago! We didn't know each other well then but still, he was musing about how long it's been since we've known each other. IF we made it into romantic arena, yes, I agree, it would most likely become serious. But I'm kinda giving up on love right now. Today we spent the whole day together in a group and he acted just like he was my date. Sat next to me at every opportunity, shared his food with me at dinner, bought my drinks, was almost always by my side. But I went home alone. I flirted, I smiled, I touched him, I was cozy at dinner. I don't have to try hard, I always like being with him anyway, it seems natural to 'flirt' because I probably always have acted that way around him. It felt like I his 'date' all day, or so I thought. Said goodbye at the end in the group, now I'm home alone, and he won't make a move. Maybe it's something about me? I see nothing wrong with us being friends but crossing the boundary into romantic territory doesn't seem likely any time soon. We've had SO many opportunities... he treats me lately as if I was his date and a girl he wants to talk to and get to know more... and be close to... but it ends there.

 

Side note... we saw each other last night in a small group setting and he said something about how a friend in the past always spoke highly about me to him, in a way as if he was encouraging him to date me. "So and always spoke very highly of you, he said she's such a pretty girl, she's so great... like I should pursue you." He said that out loud, as if he was thinking about it. That friend said that to him years ago. I don't know why at the time he didn't or what he said in response, but the friend at the time was suggesting that he should pursue me, and last night he admitted that. I also mentioned that I went to do xyz this past week, he said "you should have called me, I would like to do that with you next time". So.... what's the deal?!! I guess I can invite him with me next time, he said it, I should tell him next time so he can join me in that activity... so I will. Green light.

 

But..for whatever reason, he is holding back. Maybe there's something about me that he isn't sure about? Or maybe he feels dating within the friendship circle would be awkward? I think... neither one of us knows how to break the barrier. We both seem interested...maybe he's not 100% about me, I have no idea. It's like we are acting like we are a couple or dating but we have no romantic aspect. No holding hands, no arms around each other, no cuddling, no kissing, no sex. And I want all that. It's driving me crazy to act as if I'm dating someone and not have the physical romantic part. It makes me feel insecure that he doesn't make a move, it makes me think maybe he doesn't want me in that way and is just enjoying the platonic flirting. Very frustrated.

Edited July 22, 2018 by littlebridge

[Versacehottie]

ooohhh good! I don't think it's bad at all. It seems like you are looking for the reassurance of it moving to romantic and i can tell you guys can be slow--and very reluctant to mess up a friendship, especially if it is in the group you all hang out in. just some more patience and time. All the signs are there and he is dropping hints!!! Same things happened to most, if not all, of my friends that are in relationships with guys that were friends for a decent period of time beforehand. It's weird but they are changed really fast too, like really fast. Another girl I'm friends/acquaintances with was friends with her now husband for years and same story as yours where everyone said they should be together in their friend group. They went to a concert (different couple than my close friends), hooked up that night, decided against ruining the friendship and to stay friends and the next day changed their minds back (like why NOT take advantage of a good thing) and are married now. I think the hurdle in this type of situation is kinda huge because both of you know it will end up serious, and maybe lifelong and will have huge implications if it doesn't work out. So the leap is big.

 

You can bring up that sentence that his friend said about you guys that he brought up yesterday. Say about that, funny our other mutual friends have said similar to me at various times, have you ever thought about it? (FFS, not so formal and stiff but that's the message lol). Say this when you do that activity and are spending time alone and keep up the flirting. Like the other poster said, (didn't he?) that he and his now wife, held hands and never looked back.

 

Gosh, i have so many friends this has happened to. The music friends, went to a wedding of her friend's together and she took him as her date as they did so much together anyway as friends, and they ended up kissing and are totally together now. Other friends worked together and had a company event and hooked up and are together ever since. They had a discussion after hookup like what are we doing/should we do this over the course of a couple of days and decided to do it. BTW, on BOTH of those I had said at least a year before, he you should really this that guy (when we hung out in groups), it seems like you are a couple (so your friends do notice!!). And here we are! Oh and another friend worked with her now guy in a very small office. They hung out all the time and she liked him a lot and he did everything like they were dating except kiss her. There were a couple of times he was INCHES from her face about to. She finally flipped out on him because he wouldn't make the final move and would only talk to him at work because she had to. His excuse was that he was trying to get his career more stable (plus work being such a small office felt it was dangerous). He lasted a few days after she stopped talking to him and then came over with full confession & declaration and together ever since.

 

I really have more, just can't think of them now. I just really think in each of these cases, like yours, there is a ton at stake and at the back of their minds they know it's bound to be a serious relationship so they hold back. I wouldn't recommend the flipping out strategy lol (my other friend and i both told her it was over after that and encouraged her to move on--but we were wrong, although it was a risky strategy). You could kinda of provoke the issue with a little jealousy and envy. If he thinks he's about to miss his chance with you because you are about to start dating or that there is a good guy circling you, it might push him---though this can be risky too. Keep hanging out with him. He sounds like a good guy so he is probably more cautious then others of being frivolous.

[Iris The Butterfly]

I just really think in each of these cases, like yours, there is a ton at stake and at the back of their minds they know it's bound to be a serious relationship so they hold back. I wouldn't recommend the flipping out strategy lol (my other friend and i both told her it was over after that and encouraged her to move on--but we were wrong, although it was a risky strategy). You could kinda of provoke the issue with a little jealousy and envy. If he thinks he's about to miss his chance with you because you are about to start dating or that there is a good guy circling you, it might push him---though this can be risky too. Keep hanging out with him. He sounds like a good guy so he is probably more cautious then others of being frivolous.

 

I agree, that is why he may be holding back. He can't just casually date me, and maybe that's all he's interested in. Some guys just don't want a girlfriend. I just experienced that with someone who was also interested in me, maybe my friend feels the same. Maybe he just wants to play the field too and wants to keep it casual. Also, maybe he holds back because he wouldn't want to jeopardize the friendship, let's say that something went wrong, and it didn't work out.... I don't necessarily agree with this mindset but I get it. This is the first time that I've been available and receptive to his interest, just in the past couple months. So maybe it's a good idea to let it develop as it will naturally, whatever that means. Like I said, maybe we will just end up as friends for the rest of our lives. Who knows. All this time we've known each other so far has not been the 'right time', for various reasons.... me being involved with other relationships, now living in the same neighborhood, working in the same building, etc. I think he's probably always thought I was pretty and cool and sweet but it seems like lately the wheels have been turning as if the idea of dating me is at the forefront of his mind.

 

We haven't spoken since Saturday. I'm not sure if we will connect again this week. I may initiate or he may, we will see if another opportunity comes up. I was just planning on doing my own thing, like I always do.

 

In the meantime I'm still single and available to other men and I occasionally DO date online, nothing special and to be honest I'm considering deleting it. I would never deliberately try to make him jealous but.... I'm sure he's well aware that someone else coming in is a possibility... one of these days... maybe not a real threat. Time will tell. It always does.

 

In the meantime, I'm going to enjoy our time together, initiate one on one time when the mood strikes, and be flirtatious and receptive to the way he is acting towards me lately.

[Iris The Butterfly]

I'm going to go back on what I said in my previous post. I have another thread going and am so incredibly heartbroken and have lost all faith in love at the moment. I don't see this friendship becoming anything more any time soon. I have been excited about the potential lately but we haven't spoken since we last saw each other on Saturday, well, an email about a property but that's work related. Until it is clear as day, it isn't anything more than a flirtatious friendship. I’ve been clinging to it because I like him, I trust him. I’m lonely, horny and want a relationship.

 

I think that if he is holding back because he doesn't want to risk losing the friendship or making things awkward, then that is the way it is and it shows that he isn't sure or isn't ready or isn't that into me. I think it's perfectly ok for us to just be friends. And that's what we are.

[Versacehottie]

I'm going to go back on what I said in my previous post. I have another thread going and am so incredibly heartbroken and have lost all faith in love at the moment. I don't see this friendship becoming anything more any time soon. I have been excited about the potential lately but we haven't spoken since we last saw each other on Saturday, well, an email about a property but that's work related. Until it is clear as day, it isn't anything more than a flirtatious friendship. I’ve been clinging to it because I like him, I trust him. I’m lonely, horny and want a relationship.

 

I think that if he is holding back because he doesn't want to risk losing the friendship or making things awkward, then that is the way it is and it shows that he isn't sure or isn't ready or isn't that into me. I think it's perfectly ok for us to just be friends. And that's what we are.

 

oh wow. ok I went and read your thread in breakups. The one thing I noticed on there is where you had said that you really wanted to get married and have kids and sounded concerned about your age and time clock, etc.

 

In what i had read here, it sounds like you really like your friend (subject of this thread) even though now that i know more details about your previous bf, it sounds like you are hung up and emotionally wound up about that too. Do you think you actually feel something that could be real for this guy (the realtor friend) or just that you feel anxious to get serious with a guy, married and so on? I had felt that you were genuine about your friend in all the posts previous and not trying to force something with him that was driven by all this other stuff---it was a little like you really switched directions really quick with the post above. To me, that shows a frustration that it's not happening in some timeframe you can live with and being impatient.

 

I think the tide was just turning on you guys and it does need a little traction to turn into "something" but with your reversal it's kinda made me question what you really want from him and if it's about him or just wanting to have

someone". If he feels any of that from you, it would be something that would cause a lot of guys to hesitate in moving forward. As heartbroken as you sound about your ex, how can he not feel that and realize it and think it's the wrong time to try to be with you? It's a hard thing to hide from someone who cares about you. The overwhelming emotions, switch and impatience are a little melodramatic, sorry

 

Anyway you know what is best for you and hopefully you don't give up on love forever. I also think of course it's fine to treat him as a friend as you guys are. And sure probably a huge part of him not wanting to move forward is because he doesn't want to risk the friendship. He could also not be ready and that's fair enough. Same way he could potentially feel that you aren't ready, right? Because if you are that heartbroken (which it sounds like it), that's also fair--i'm sure he doesn't want to be a rebound. Ok hang in there. The frustration will pass because if you want love, it needs to so you can get up and try again (with whoever).

[Iris The Butterfly]

oh wow. ok I went and read your thread in breakups. The one thing I noticed on there is where you had said that you really wanted to get married and have kids and sounded concerned about your age and time clock, etc.

 

In what i had read here, it sounds like you really like your friend (subject of this thread) even though now that i know more details about your previous bf, it sounds like you are hung up and emotionally wound up about that too. Do you think you actually feel something that could be real for this guy (the realtor friend) or just that you feel anxious to get serious with a guy, married and so on? I had felt that you were genuine about your friend in all the posts previous and not trying to force something with him that was driven by all this other stuff---it was a little like you really switched directions really quick with the post above. To me, that shows a frustration that it's not happening in some timeframe you can live with and being impatient.

 

I think the tide was just turning on you guys and it does need a little traction to turn into "something" but with your reversal it's kinda made me question what you really want from him and if it's about him or just wanting to have

someone". If he feels any of that from you, it would be something that would cause a lot of guys to hesitate in moving forward. As heartbroken as you sound about your ex, how can he not feel that and realize it and think it's the wrong time to try to be with you? It's a hard thing to hide from someone who cares about you. The overwhelming emotions, switch and impatience are a little melodramatic, sorry

 

Anyway you know what is best for you and hopefully you don't give up on love forever. I also think of course it's fine to treat him as a friend as you guys are. And sure probably a huge part of him not wanting to move forward is because he doesn't want to risk the friendship. He could also not be ready and that's fair enough. Same way he could potentially feel that you aren't ready, right? Because if you are that heartbroken (which it sounds like it), that's also fair--i'm sure he doesn't want to be a rebound. Ok hang in there. The frustration will pass because if you want love, it needs to so you can get up and try again (with whoever).

 

 

I genuinely like him and am interested, not because of my age or desire to settle down or being heartbroken. I’ve had a crush on him for over 4 years. It’s just that lately I’ve noticed more how great of a guy he really is. We’ve gotten to know each other more lately, so my attraction has increased. And also, I admit that once that guy I was seeing mentioned that he felt my friend was “totally in love” with me, I really started to pay attention.

 

Thanks for reading my other thread. It’s a tear jerker, huh? Yes, my heart is definitely broken. I’m not sure if I’m ‘on the rebound’ but I am very frustrated, feeling disillusioned, sad, etc. But it really has nothing to do with my interest in my friend at all. Only that I feel myself more drawn to him lately because I trust him and I like him … and I admit I like the attention and affection he gives to me lately. I’ve always liked him but I find myself liking him more. I AM frustrated because I want to date and date someone that I trust… like him. So I get impatient. I gave up online dating and am not looking or interested in meeting and dating any strangers so naturally I feel compelled to him. We seek what feels safe and that’s what I’m doing.

 

I think he holds back, for ‘not wanting to risk the friendship’, or maybe you are right, he sees that I was really hurt by that guy and still healing. Someone else mentioned that maybe that was the case. I don’t know. They met several times and he knows the whole break up story.

 

But hey, something has come up tonight. We had been emailing this week about home stuff and he asked if I was free after work tonight to go see a couple places that came up that I’m interested in since he wouldn’t be around this weekend. My parents happen to be coming for dinner and now they want to join so they will meet him for the first time. It would be nice if he came for dinner but I’m too shy to ask, I doubt he will come. I’ve spent time with his parents and family but never just one on one. My mom knows all this, she is rooting for this to happen. It has to be mutual. I know that he likes me and respects me and cares for me. I just don’t know if he is on board and ready to date me and cross over to that territory. Time will tell.