First First Date in 17 Years

[jcm 800]

Thank you for the advice, and I didn't take it as criticism at all. My gut was telling me to keep my mouth shut, but I also didn't want to take the chance I screwed something up by not mentioning anything. This is the first online date I've gone on, and my past relationships grew organically from friendships.

 

It really did feel a bit unnatural and pressured last week. I felt like I couldn't be myself because there we so many expectations. Funny thing is that I am being myself now, and it seems like everything is flowing more naturally.

[Highndry]

As I mentioned before, we are going out as friends for lunch tomorrow. Having said that, I now get the feeling via some things that were said in texts from this past week that there is still potential for something more. Almost like we're testing to see how we get along without the pressure of dating. I don't want to rush anything, and certainly don't want to put any pressure on her. Not my style.

 

Believe it or not, I've never been in this exact situation before. She already knows I think she's attractive (I told her), and I already know she thinks I'm attractive (she told me), and she said she liked me, but felt she was still working through something with her ex. There's part of me that's thinking of saying something along the lines of "I like you, let's just hang out as friends, and if anything else comes up, we'll cross that bridge."

 

Or should I just keep my mouth shut, hang out, and see what happens? Just not sure if I should address it or not.

 

I'm OK if we are just friends, but I'd be lying through my teeth if I said I wasn't attracted to her.

 

Don't say anything, I think that would be a mistake. Also, if you have romantic feelings for her, I would definitely NOT go for the friends thing. I would continue on and treat the meetings like dates, flirting with her just as you would any other gal you were interested in.

[jcm 800]

Let's just say I wasn't planning on wearing my beat up Pink Floyd t-shirt.....

[jcm 800]

We went and had lunch today, and ended up staying and talking for over an hour and a half. Went much smoother today, we both seemed more like ourselves, and we were both laughing and joking a lot. She complemented the way I did my hair and was twirling her hair quite a bit. Much more laid back. She also paid; I had paid last week, and just assumed we'd go dutch this week.

 

We were just talking about our daily lives, family, etc., and she made it a point to tell me she isn't bossy, or controlling. Not sure if I'm reading too much into that (likely am, I tend to do that). I wondered why she something like that, like if she was trying to say hey, don't worry, if we go further, I won't be the controlling, bossy girlfriend. I didn't get the vibe off of her that she was either one of those things, and I told her so. I had a lot of fun. She seems like a really great person, and I can definitely see me wanting to take it further.

 

Not sure where, if anywhere else this is going to go. She had mentioned to me that she preferred not meeting people online, and that she liked the slow build when you first meet someone that then connection forms. I kind of prefer this too. Going to keep on keeping on at this point, but I do fall hard, so I'll need to keep that in check while this whole thing unfolds.

 

I won't post updates for every little thing. CautiouslyOptimistic and Highndry, I really want to thank you. I sometimes have a hard time when I meet new people, and I got through it, semi-relaxed, and was able to be myself because of your advice. You both really helped me out a lot, and I appreciate it very much.

Edited October 28, 2017 by jcm 800

[Highndry]

We went and had lunch today, and ended up staying and talking for over an hour and a half. Went much smoother today, we both seemed more like ourselves, and we were both laughing and joking a lot. She complemented the way I did my hair and was twirling her hair quite a bit. Much more laid back. She also paid; I had paid last week, and just assumed we'd go dutch this week.

 

We were just talking about our daily lives, family, etc., and she made it a point to tell me she isn't bossy, or controlling. Not sure if I'm reading too much into that (likely am, I tend to do that). I wondered why she something like that, like if she was trying to say hey, don't worry, if we go further, I won't be the controlling, bossy girlfriend. I didn't get the vibe off of her that she was either one of those things, and I told her so. I had a lot of fun. She seems like a really great person, and I can definitely see me wanting to take it further.

 

Not sure where, if anywhere else this is going to go. She had mentioned to me that she preferred not meeting people online, and that she liked the slow build when you first meet someone that then connection forms. I kind of prefer this too. Going to keep on keeping on at this point, but I do fall hard, so I'll need to keep that in check while this whole thing unfolds.

 

I won't post updates for every little thing. CautiouslyOptimistic and Highndry, I really want to thank you. I sometimes have a hard time when I meet new people, and I got through it, semi-relaxed, and was able to be myself because of your advice. You both really helped me out a lot, and I appreciate it very much.

 

Great news. I think it's important to remind yourself that she needs to meet your standards, too, it's not just about her. I say this because sometimes as men we tend to think that it's our job to prove ourselves as if she's the prize when in reality the woman needs to do the same. You seem like a good catch for her.

 

That being said, I do think that if anything romantic is going to happen between you two, you probably need to escalate sooner rather than later. Otherwise, you're headed for the dreaded friend zone. If there's no kissing by 2 or 3 dates, it is not a good sign at all. Good luck.

[coolheadal]

So it got changed from coffee to a lunch date, which is very cool. It's also going to be warmer here than I thought today. The shirt I planned on wearing originally may be a little too heavy. I have two other shirts that are appropriate, but I was wearing them in my profile pics. Any reason I can't wear them today, or is that not cool?

 

Can you tell it's been a while since I've done this....?

 

Dress shoes might be too much for coffee, white canvas shoes, cream color chino pants, no show socks, light blue long sleeve shirt. Wear large crown matching watch, you can also wear one or two men leather bracelet. Dark sunglasses, hair style should be today's look shave low and high blend with your hair on top. You should smell clean fresh. If you smoke chew some mint gum.

[jcm 800]

Good point about meeting my standards. I didn't think consciously about that, but there have already been a few that I interacted with online that I knew right away weren't what "up to my standards..." Has NOTHING to do with appearance, by the way. I just knew we weren't going to work.

 

I got the vibe she was treating it somewhat like a date today, but still as friends, if you know what I mean. Not sure how I would escalate it just yet without coming off like a jerk, and I really don't want to pressure her, especially since she said she wasn't sure she was still getting over her ex. None of that came up today, by the way.

 

I did notice she took her online dating down. I also did the same, but just because I need a break from it.

[coolheadal]

We went and had lunch today, and ended up staying and talking for over an hour and a half. Went much smoother today, we both seemed more like ourselves, and we were both laughing and joking a lot. She complemented the way I did my hair and was twirling her hair quite a bit. Much more laid back. She also paid; I had paid last week, and just assumed we'd go dutch this week.

 

We were just talking about our daily lives, family, etc., and she made it a point to tell me she isn't bossy, or controlling. Not sure if I'm reading too much into that (likely am, I tend to do that). I wondered why she something like that, like if she was trying to say hey, don't worry, if we go further, I won't be the controlling, bossy girlfriend. I didn't get the vibe off of her that she was either one of those things, and I told her so. I had a lot of fun. She seems like a really great person, and I can definitely see me wanting to take it further.

 

Not sure where, if anywhere else this is going to go. She had mentioned to me that she preferred not meeting people online, and that she liked the slow build when you first meet someone that then connection forms. I kind of prefer this too. Going to keep on keeping on at this point, but I do fall hard, so I'll need to keep that in check while this whole thing unfolds.

 

I won't post updates for every little thing. CautiouslyOptimistic and Highndry, I really want to thank you. I sometimes have a hard time when I meet new people, and I got through it, semi-relaxed, and was able to be myself because of your advice. You both really helped me out a lot, and I appreciate it very much.

 

Oops.. She said didn't want to meeting anyone online and she wants to take things slow.. Slow dragging it out. If you have the time for that you can give her a try, but keep your options open and date other women until you and her can be more of item instead of just friends hanging out and going dutch. Sounds like she's a family gal. See how it goes in the later days, weeks, months and years. I my can't wait so long.. I am doing that now it's like 3 months of waiting.. Family issues on her end, my ex GF contacted me I don't know why after 2 years NC.. We're just emailing back and force we're both busy, single people. Anyway the current is away, I'll go back to sleep now! Good luck!

[jcm 800]

She said meeting online wasn't her preferred method. This is my first time doing that, and I can say I feel the same way. My other relationships grew organically from friendships, and I am much more comfortable with that.

 

I'm not sure I'M comfortable pushing things so that we're going further in the next date or two. Am I wrong (and I'm serious...) to think that it's OK to move slowly, and then see where it goes? I know I'm not OK multi-dating, and I don't necessarily feel like I have to move on to someone else just because we haven't kissed by a certain time. I mean, she was MUCH more open and a hell of a lot less guarded today than she was on our official "date" last week.

 

I know that it may never go any further, but I let my last relationship slowly build, and we were together for 17 years, and married for 13 of them.

Edited October 28, 2017 by jcm 800

[CautiouslyOptimistic]

She said meeting online wasn't her preferred method. This is my first time doing that, and I can say I feel the same way. My other relationships grew organically from friendships, and I am much more comfortable with that.

 

I'm not sure I'M comfortable pushing things so that we're going further in the next date or two. Am I wrong (and I'm serious...) to think that it's OK to move slowly, and then see where it goes? I know I'm not OK multi-dating, and I don't necessarily feel like I have to move on to someone else just because we haven't kissed by a certain time. I mean, she was MUCH more open and a hell of a lot less guarded today than she was on our official "date" last week.

 

I know that it may never go any further, but I let my last relationship slowly build, and we were together for 17 years, and married for 13 of them.

 

So glad to hear about your very good date today, and I think it's perfectly fine, and much healthier!, to take your time. Most OLD relationships progress WAY too quickly.

[jcm 800]

So glad to hear about your very good date today, and I think it's perfectly fine, and much healthier!, to take your time. Most OLD relationships progress WAY too quickly.

Thank you! Not because you agree with me (well, somewhat...) but I was hoping for a female's perspective on this. I agree totally that things move a little too quickly, FOR ME. Maybe I'm old fashioned for a 44 year old guy, but I would much rather build something lasting and with a connection first. I feel the physical aspect, and all of that stuff will happen if you've got the foundation there. Whatever works for someone else is cool with me, so Highndry and Coolheadal, please don't think I'm passing judgement on you, or think I don't value your advice. i just know that I can't work on a schedule with something like this. I don't want to possibly toss something cool away just because it doesn't meet certain deadlines, etc. And I do feel like something could be there with this. I'd rather take a chance and wait it out, and if it doesn't move beyond friendship, that's OK

Edited October 28, 2017 by jcm 800

[CautiouslyOptimistic]

Thank you! Not because you agree with me (well, somewhat...) but I was hoping for a female's perspective on this. I agree totally that things move a little too quickly, FOR ME. Maybe I'm old fashioned for a 44 year old guy, but I would much rather build something lasting and with a connection first. I feel the physical aspect, and all of that stuff will happen if you've got the foundation there. Whatever works for someone else is cool with me, so Highndry and Coolheadal, please don't think I'm passing judgement on you, or think I don't value your advice. i just know that I can't work on a schedule with something like this. I don't want to possibly toss something cool away just because it doesn't meet certain deadlines, etc. And I do feel like something could really be there with this. I'd rather wait it out, and if it doesn't move beyond friendship, that's OK

 

As a 44 year old woman, I can tell you that I'm sure she will appreciate this mindset. She's a lucky lady. It shows respect, and it also shows that you're actually ready for a relationship because you only want it if it's right, not just because it is there.

 

She sounds lovely .

[jcm 800]

As a 44 year old woman, I can tell you that I'm sure she will appreciate this mindset. She's a lucky lady. It shows respect, and it also shows that you're actually ready for a relationship because you only want it if it's right, not just because it is there.

 

She sounds lovely .

Thank you.

 

Couple other questions, Cautiously, if you don't mind. Where do I go from here? Do I ask if she wants to get together as friends again? How long do I wait? Do I wait and she if she asks? This is the part of the whole "game" that I never got.

[CautiouslyOptimistic]

Thank you.

 

Couple other questions, Cautiously, if you don't mind. Where do I go from here? Do I ask if she wants to get together as friends again? How long do I wait? Do I wait and she if she asks? This is the part of the whole "game" that I never got.

 

I'd text her tonight before bed and thank her again for lunch today, tell her you're enjoying getting to know her, and say goodnight/sweet dreams. Maybe compliment her on an aspect of her personality (i.e. "you're so easy to talk to.") Tomorrow text again to just wish her a relaxing Sunday or if you're free, and she's free, you could suggest something very casual like watching the football game together (if you both like football and your team is even playing). I wouldn't say "as friends." That is not necessary at this point, in my opinion. You've already talked about that. Just casually invite her to something already happening (like football or a brewfest or something). If nothing is going on that you can invite her to, I'd probably just wish her a nice day, keep up casual texting and ask her to do something one night this week, like grab a drink (if you drink) or coffee after work, if you both work traditional 9-5 jobs. Wait to ask her on Tuesday or something. Of course I have no clue about your schedules .

 

She also may surprise you and ask you to do something .

 

It's also always nice, to me, if someone texts me a random meme or news article about something we've talked about or something that reminds them of me....could be funny (meme) or even serious (news article). It just lets her know that you thought of her in a light-hearted way, and also tells her more about you, what you find funny, what catches your eye.

[jcm 800]

I'd text her tonight before bed and thank her again for lunch today, tell her you're enjoying getting to know her, and say goodnight/sweet dreams. Maybe compliment her on an aspect of her personality (i.e. "you're so easy to talk to.") Tomorrow text again to just wish her a relaxing Sunday or if you're free, and she's free, you could suggest something very casual like watching the football game together (if you both like football and your team is even playing). I wouldn't say "as friends." That is not necessary at this point, in my opinion. You've already talked about that. Just casually invite her to something already happening (like football or a brewfest or something). If nothing is going on that you can invite her to, I'd probably just wish her a nice day, keep up casual texting and ask her to do something one night this week, like grab a drink (if you drink) or coffee after work, if you both work traditional 9-5 jobs. Wait to ask her on Tuesday or something. Of course I have no clue about your schedules .

 

She also may surprise you and ask you to do something .

 

It's also always nice, to me, if someone texts me a random meme or news article about something we've talked about or something that reminds them of me....could be funny (meme) or even serious (news article). It just lets her know that you thought of her in a light-hearted way, and also tells her more about you, what you find funny, what catches your eye.

 

I do have a gig tonight - I just gave my notice with this band; we're not very good, or else I would have invited her, (we were laughing about it today), but I will make it a point to text her. I already have the joking meme I can send her too.

 

Thank you again

[jcm 800]

This may be a bit long...I apologize in advance.

 

Since I last posted, it does feel like some things have progressed a bit, but it does feel like we're both sending signals that we want to be more than friends. We now text just about daily, and have been out once more. It seemed like we both a bit more invested the last time we went out, even though it was only as friends. We were both dressed a little better, and the conversation got more personal. She was asking me a bit about my ex (I am coming out of a 13 year marriage) and a bit about my past; nothing out of the question, in fact I took it as a sign of interest. I didn't mind answering the questions, and told her that I felt like I didn't know what I should or shouldn't say, so I kind of kept it quiet. She answered by telling me to just be myself with her.

 

The texts have also been more personal lately; her sending one right before I have a gig (I'm a musician) wishing me good luck, and me asking her questions about the various organizations she volunteers for. Talking about our families. Not every text every day is like that; some days they're quick, short exchanges. Scheduling has been crazy for both of us, so that did play a factor in the amount of time that passed since we were able to actually go out together.

 

I have still been a bit "guarded" with her, because she did say after the first time we went out that she liked me, but wasn't sure she was ready to date yet because she was still working through something. I want to make sure I respect that, and don't want to pressure her. Having said that, I do genuinely like her, and want to be more "myself" with her. I'm thinking of sending this to her via text:

 

"I hope you don’t mind but I just wanted to say that I think you’re a great person. It’s awesome that you volunteer for so many organizations, and it says a lot about who you are. I really like talking with you, and have really enjoyed getting to know you. I wanted to say this when we were out Saturday, but didn’t because I want respect what you said about not being ready to date, and didn’t want to come across like I was pressuring you for anything more, but I also just wanted to share how I was feeling."

 

What do you guys think? Of course I would rather do it in person, but I also just feel like I really want to open up a bit. One of the issues she had with her ex was that he was emotionally unavailable. I have that same issue with my ex, and I don't want to be that type of person.

Edited November 14, 2017 by jcm 800

[CautiouslyOptimistic]

This may be a bit long...I apologize in advance.

 

Since I last posted, it does feel like some things have progressed a bit, but it does feel like we're both sending signals that we want to be more than friends. We now text just about daily, and have been out once more. It seemed like we both a bit more invested the last time we went out, even though it was only as friends. We were both dressed a little better, and the conversation got more personal. She was asking me a bit about my ex (I am coming out of a 13 year marriage) and a bit about my past; nothing out of the question, in fact I took it as a sign of interest. I didn't mind answering the questions, and told her that I felt like I didn't know what I should or shouldn't say, so I kind of kept it quiet. She answered by telling me to just be myself with her.

 

The texts have also been more personal lately; her sending one right before I have a gig (I'm a musician) wishing me good luck, and me asking her questions about the various organizations she volunteers for. Talking about our families. Not every text every day is like that; some days they're quick, short exchanges. Scheduling has been crazy for both of us, so that did play a factor in the amount of time that passed since we were able to actually go out together.

 

I have still been a bit "guarded" with her, because she did say after the first time we went out that she liked me, but wasn't sure she was ready to date yet because she was still working through something. I want to make sure I respect that, and don't want to pressure her. Having said that, I do genuinely like her, and want to be more "myself" with her. I'm thinking of sending this to her via text:

 

"I hope you don’t mind but I just wanted to say that I think you’re a great person. It’s awesome that you volunteer for so many organizations, and it says a lot about who you are. I really like talking with you, and have really enjoyed getting to know you. I wanted to say this when we were out Saturday, but didn’t because I want respect what you said about not being ready to date, and didn’t want to come across like I was pressuring you for anything more, but I also just wanted to share how I was feeling."

 

What do you guys think? Of course I would rather do it in person, but I also just feel like I really want to open up a bit. One of the issues she had with her ex was that he was emotionally unavailable. I have that same issue with my ex, and I don't want to be that type of person.

 

I think that's a very sweet text and she's a lucky lady to receive it .

[jcm 800]

Thank you, Cautiously. It's tough for me to open up sometimes, but I'm therapy, and just taking chances have made it a lot easier for me. I don't want her to get the impression that I'm not interested, or a completely closed off guy. I'm actually far from it.

[CautiouslyOptimistic]

What I like about the text is that you didn't mention anything at all about her physical appearance. You spoke about the things that truly matter and I think she will like that a lot.

[jcm 800]

Honestly, that's not my primary concern at the moment. If the foundation is there, all the physical, appearance, etc. will also be there. I am not, and have never been the player type.

 

My marriage fell apart, and had been falling apart for a long time. I worked through a lot of that. I don't know everything that I want right now, but I have a pretty good idea, and I do know what I don't want. The fact that I feel like I can connect with her on a higher level than just "I think you're hot" is attractive to me.

 

Yes, I do think she is beautiful, but I learned from my marriage that there is a hell of a lot more needed if you want to be happy.

Edited November 14, 2017 by jcm 800

[jcm 800]

My only other thing at this point (because I wouldn't be me if I didn't over analyze), is when should I send it. Does it matter? We sometimes do text during the work day, and not at night. I also know that tonight is a night she works late. I don't want to do anything inappropriate.

Edited November 14, 2017 by jcm 800

[1fish2fish]

I hope I'm lucky enough to meet a guy like you. You sound lovely.

[Highndry]

I have a different opinion as a man. I wouldn't send that text. It sounds too needy and approval seeking, like you're afraid to say/do certain things around her. I would focus solely on taking things to the next level in person. I think you need to move in and kiss her. Don't be scared.

[jcm 800]

I'm honestly not afraid, just trying to be respectful. One of the reasons my marriage fell apart was that there was no real respect or caring for my needs at all. She stated her wants, etc, and I'm going to abide by that, and if and when it feels right, escalate slowly. She was pretty adamant that she was working through something, and I think it's cool that we're still corresponding and possibly building something. I rush into my last relationship. Not doing it again.

[jcm 800]

I guess we'll see what happens....she texted me first today, so I responded and also said what I needed to say.