When Friends Try to Date

[2013k]

So, there is this guy that I have been friends with for about 5 years now. I've always thought he was really cute/cool, but I always figured we were just meant to be friends. Well, a few months ago, I sent him a link to some new tunes that I thought he would like, and he wrote me back and asked me out. I kind of ignored his email because I was seeing someone else at the time, but when that ended, I sent him a little Happy New Year note and suggested that we go grab the drink we missed out on in 2012.

 

We did that, and we had fun, but it was a bit of an awkward, traditional date...and I don't think either of us were sure whether the other felt it was a date since we've been friends for so long. At the end of the evening, he gave me a gift of his bands' entire discography, and as I was walking home thinking that I blew it, he shot me a text that said, "Hey maybe we can grab a drink this weekend after my in-store show."

 

So, I went to the show, but then he had to do an interview and I went to a friend's BBQ, and we ended up not getting the drink. The next day I got a text from him apologizing, and he asked if I wanted to maybe hang out later that week. Later that week came around, and I didn't hear from him. Then, last Monday, he emailed me and said he was sorry and that he knows we are both super busy but that he'd really like to see me again. He ended his email with, "And I think you are really smart, sexy and cool."

 

I emailed him back and told him I'd be free the next week since I had guests in town, but then he didn't respond. While I was out with my friends, I sent him a casual funny text about our night, and then we exchanged a few short texts back and forth over the weekend. Still no mention of our future plans...

 

So, what gives? Why would a guy break out friend barrier and tell me that I'm smart, sexy and cool, only to flake out?

 

Is it possible that I'm just not sending the right signals? Or should I just write him off?

 

I emailed him the following today, but now I'm worried that I came off as a little crazy:

"Hey! So...you still up for hanging out sometime this week? If so, I say we meet around 7:30 pm on Thursday at the Matchbox (or some other cozy, dark watering hole). Either that or we try to locate this movie in Chicago, grab a sixer, go to one of our houses and enjoy the most wonderfully bizarre sci-fi on Earth: [a link to a nerdy sci-fi indie film that I know we'd both love since we're both into that sort of thing]

 

 

For what it's worth, I think you're also "smart, sexy and cool." But if something's holding you back, we can stick with the awesome camaraderie we've had for the past 4+ years, and I won't be weird or offended. I'll still be an attorney who shares new music with you from time to time, and you'll still be a designer/professor who makes some of my favorite tunes. :-)

 

 

Hope you had a fun Super Bowl Sunday!"

 

So, what do you guys think about this situation? Did I blow it? Do I still have a chance?

[Talak7]

You're fine.

Men like e-mails and such that clearly read a lack of pressure and encourage a good relationship no matter his own decision.

 

Just wait for a response and don't bother him until then. It's in his court.

[pbjbear]

Flakiness generally means not interested

 

Dont listen to what men say.

Dont listen to what men say.

Dont listen to what men say.

 

I typed it 3 times because men will say what they need to without meaning it. Men know women think with their ears...

 

Look at what a guy does. Flakiness generally means not interested. He might like you some, but not enough.

 

Its a little soon to tell, but if this continues Id say hes not all that interested. It could be its awkward for him and he hasnt warmed up, hes busy or whatnot give it some more time first.

[Talak7]

Flakiness generally means not interested

 

Dont listen to what men say.

Dont listen to what men say.

Dont listen to what men say.

 

I typed it 3 times because men will say what they need to without meaning it. Men know women think with their ears...

 

Look at what a guy does. Flakiness generally means not interested. He might like you some, but not enough.

 

Its a little soon to tell, but if this continues Id say hes not all that interested. It could be its awkward for him and he hasnt warmed up, hes busy or whatnot give it some more time first.

 

 

Better yet, don't take advice from people that make huge generalizations about a large group of people. It's indicative of a skewed perception due to their own personal bias.

 

YES, judge everyone by their actions and not their words. But not after such a relatively short amount of time compared to a friendship of 5 years?

 

My girl friends from 5 years often don't take me back randomly or end of flaking - and I end up randomly flaking on them too if something else comes up.

 

Why?

 

BECAUSE WE'VE BEEN FRIENDS FOR 5 YEARS SO IT'S NOT REALLY A BIG DEAL!

 

Seriously- You didn't have a time+place+date confirmed together and he e-mailed you before your original plan complimenting you and trying to make plans in the future.

Just because your perspective has changed doesn't mean his has. You did exactly what you should do, from here on it's entirely up to his next move. Just wait for that.

[pbjbear]

Better yet, don't take advice from people that make huge generalizations about a large group of people. It's indicative of a skewed perception due to their own personal bias.

 

YES, judge everyone by their actions and not their words. But not after such a relatively short amount of time compared to a friendship of 5 years?

 

My girl friends from 5 years often don't take me back randomly or end of flaking - and I end up randomly flaking on them too if something else comes up.

 

Why?

 

BECAUSE WE'VE BEEN FRIENDS FOR 5 YEARS SO IT'S NOT REALLY A BIG DEAL!

 

Seriously- You didn't have a time+place+date confirmed together and he e-mailed you before your original plan complimenting you and trying to make plans in the future.

Just because your perspective has changed doesn't mean his has. You did exactly what you should do, from here on it's entirely up to his next move. Just wait for that.

 

You sound unstable. You flip out on everyone and sound so angry in all your posts.

 

You should judge someone by what they do. Words are cheap. Actions are louder than words. I gave my thoughts on that subject because most women give too much emphasis on words. Flakiness generally does mean someone is not interested- when you like someone you will want to respond to them and make plans.

 

I didnt say he wasnt interested but that it was too early to tell.

Edited February 4, 2013 by pbjbear

[Talak7]

You sound unstable. You flip out on everyone and sound so angry in all your posts.

 

You should judge someone by what they do. Words are cheap. Actions are louder than words. I gave my thoughts on that subject because most women give too much emphasis on words. Flakiness generally does mean someone is not interested- when you like someone you will want to respond to them and make plans.

 

I didnt say he wasnt interested but that it was too early to tell.

 

The way you read my posts is not indicative of the way I type my posts. Don't lay your own emotions down upon it just because I call you out on your terrible generalizations in every thread.

 

You consistently give false, terrible advice to people and make huge generalizations about men. You are not a man. You only wish you knew what men thought. But if you did, you wouldn't say such ridiculous things in a variety of your posts. Your own bitterness has always developed a personal bias to certain situations, and instead of considering the possibilities, you use inherently flawed universal rules to dictate your life.

 

Your problem is, you are the type of person to scream

"DONT LISTEN TO WHAT MEN SAY!!!" and then later call it " I gave my thoughts on that subject because most women give too much emphasis on words.. "

 

So yes, take advice from her and blow him off cause he obviously doesn't care.

 

I'm not saying don't judge people by their actions.

But you're saying that his actions are flaky and they could be completely different things going on.

All he did was cancel a plan before it began (not flaking - Things happen. Flaking = Standing you up , ditching you consistently, making unclear plans then not responding, etc).

 

The fact is- He hasn't even flaked at all yet.

When he actually flakes out on you, then you should call him out on it and stop wasting your time.

 

 

It's natural for bitter people to come to these forums and jump the gun because of their own crappy relationships.

 

Just practice due diligence

[carhill]

So, what gives? Why would a guy break out friend barrier and tell me that I'm smart, sexy and cool, only to flake out?

 

Platonic friends who are busy don't assign emotions to each other's 'busy-ness'.

 

Friends transitioning or wishing to transition from platonic to romantic relations *both* should employ patience in making the transition. Different rules apply compared to otherwise unknown romantic potentials. Behavioral sets necessarily change and that takes time *and* clear communication.

 

Since you're friends, how about communicating directly how you *feel*? If the gentleman was here asking for advice, I'd tell him the same thing. You have a common base of synergistic relations and trust and care. Capitalize upon it. Good luck.

[2013k]

Thanks for the advice, everyone! He contacted me today and asked me if I want to watch that movie with him and hang out at his dad's swanky vacation condo, which just so happens to be in the city where we live.

 

Now I am nervous about the next steps. I think he is showing some interest since he wants to hang out somewhere cool with a view rather than at his place, which is a live/work artist loft with a couple roommates. I want to make sure we stick to a snail's pace so that means resisting the temptation to get overly frisky while also maintaining genuine, real conversation.

 

Any tips on how to calm my nerves before I meet up with him? Also, should I bring something, like wine or a nice craft beer? Or should that be his job? Any how-to-go-on-a-date-with-your-friend advice is greatly appreciated!

[Talak7]

See! I called it!!

The jaded attitude gets ya nowhere.

 

 

Just bring wine! Also swanky condo with a view is a great sign. A bit forward...! I'm sure you'll be fine.

 

Guys that like girls like when they are you a bit nervous- it's flattering

[Mrlonelyone]

It sounds to me like the original poster hasn't really given the right signals of interest.

 

This man lives in the same world as the rest of us. He's heard the term friendzone, and he's been friends with this woman for years. On some level he has to be afraid that she's not really interested. Just as afraid as she is.

 

OP if you like this man do the following. Ask him out on a date with a set place, and time. It can be your going to meet up and hang out at place X,Y,Z and time T. It can't be your going to hang out someplace and sometime.

 

Unless there is a firm plan it's not flaking.

[Talak7]

It sounds to me like the original poster hasn't really given the right signals of interest.

 

This man lives in the same world as the rest of us. He's heard the term friendzone, and he's been friends with this woman for years. On some level he has to be afraid that she's not really interested. Just as afraid as she is.

 

OP if you like this man do the following. Ask him out on a date with a set place, and time. It can be your going to meet up and hang out at place X,Y,Z and time T. It can't be your going to hang out someplace and sometime.

 

Unless there is a firm plan it's not flaking.

 

No offense just read whole thread for updated situation

[Mrlonelyone]

Oops. Well she still shouldn't be afraid to ask him for what she wants.

[2013k]

Thanks, guys! Your comments have all been awesome...even the not so promising ones.

 

Now I just have to decide what to wear! :-)

[pbjbear]

See! I called it!!

The jaded attitude gets ya nowhere.

 

 

Just bring wine! Also swanky condo with a view is a great sign. A bit forward...! I'm sure you'll be fine.

 

Guys that like girls like when they are you a bit nervous- it's flattering

 

Where did I EVER say for her to blow him off?

Stop putting words in my mouth and actually read. You say I have said things I have not written.

 

I said its TOO EARLY TO TELL but if he continues to be flakey it means hes not interested

A few dates is not enough, but when you date someone longer than that and they are flakey IT DOES mean someone isnt that interested unless they have a demanding and infelxible work schedule...this isnt rocket science

 

Yes women do put too much emphasis on words. So many women on this forum that date a guy whose actions clearly show they arent that interested yet they excuse his behavior because he says *this* or *that*

 

*facepalm*

Edited February 5, 2013 by pbjbear

[pbjbear]

Flakiness generally means not interested

 

 

Its a little soon to tell, but if this continues Id say hes not all that interested. It could be its awkward for him and he hasnt warmed up, hes busy or whatnot give it some more time first.[/QUOTE]

 

How the **** is that being jaded?

 

Thats level headed advice.

[2013k]

I think pbjbear might have gotten things right. So, I went on the date with my friend last week on Tuesday. We hung out at his dad's cute condo downtown. We spent the evening chatting, laughing and splitting a couple beers. Before we knew it, it had gotten a bit late, but we still decided to watch the movie together. At that point, we sat closer together on the couch, held hands and got pretty cozy...but still no kiss.

 

Then about an hour into the movie, he just went for it, and we spend about 30 minutes making out like high schoolers. It was hot and it was sexy and it was exciting. After a while, he tried to go for my skirt, but I stopped him, and in a Girls-esque moment, I said something like, "I like this and I am having fun, but I don't want to let this make things weird between us. You know how much I love your band. I don't want to get to a point where I can't anymore." (I know, facepalm, what the heck was I thinking/saying!)

 

And then he responded, "No, I mean, it's okay. We can keep it casual if you want."

 

And then I tried to recover the moment, and we were back to making out, with him saying the typical guy stuff, "You're so sexy. I just want to make you feel good." Etc. etc.

 

And then at some point, I told him it was getting late, and he asked me if I wanted him to give me a ride home. And then I said, "Yeah, that would be great." And he said, "Well, just wait one more minute." And he kissed me again. He'd managed to put his hands on the outside of my tights, and let's just say it felt great. He tried to lead my hand to the outside of his own pants, and when he did that, I just said, "You know. Let's not do that, but I don't have to go home right now. It's super late. We can just go to bed and I'll hop in a cab to my house in the morning."

 

After that, he kind of jumped into gentleman mode. He even asked me if it was okay for him to sleep in the bed with me rather than on the couch...as if that was something I had implied. And then he asked if it was okay for him to sleep in his boxers instead of his jeans. We snuggled up and slept in each other's arms comfortably through the night, and then when we woke up, he got dressed and walked with me to search for a cab in the morning rush traffic. In a swift wave of the cab and a kiss on the cheek, I was off to grab my bags and head to the airport for a trip I had planned last week.

 

We had fun, and the evening was great, but now we're back to quiet. He responded to a text I sent him while I was away, because I randomly met some mutual friends of his at a bar while on my trip. And then he randomly started following me on Instagram yesterday.

 

Other than that, no contact.

 

It's a bummer. Something is holding him back, and that's okay, but I really hope I didn't just let our evening ruin our friendship.

 

Should I say something to him at some point? If so, what and when? Or should I just keep my distance and hope he comes around either for a 3rd date or just to rekindle our formerly platonic relationship? Thoughts?

[pbjbear]

I wish I wasnt. *hugs*

 

Most of the time if you have to guess if a guy likes you or not, he doesnt like you that much.

 

I think its a little early to say something, but thats just me. If you want to, go for it. Id wait a few more dates...

[todreaminblue]

I think pbjbear might have gotten things right. So, I went on the date with my friend last week on Tuesday. We hung out at his dad's cute condo downtown. We spent the evening chatting, laughing and splitting a couple beers. Before we knew it, it had gotten a bit late, but we still decided to watch the movie together. At that point, we sat closer together on the couch, held hands and got pretty cozy...but still no kiss.

 

Then about an hour into the movie, he just went for it, and we spend about 30 minutes making out like high schoolers. It was hot and it was sexy and it was exciting. After a while, he tried to go for my skirt, but I stopped him, and in a Girls-esque moment, I said something like, "I like this and I am having fun, but I don't want to let this make things weird between us. You know how much I love your band. I don't want to get to a point where I can't anymore." (I know, facepalm, what the heck was I thinking/saying!)

 

And then he responded, "No, I mean, it's okay. We can keep it casual if you want."

 

And then I tried to recover the moment, and we were back to making out, with him saying the typical guy stuff, "You're so sexy. I just want to make you feel good." Etc. etc.

 

And then at some point, I told him it was getting late, and he asked me if I wanted him to give me a ride home. And then I said, "Yeah, that would be great." And he said, "Well, just wait one more minute." And he kissed me again. He'd managed to put his hands on the outside of my tights, and let's just say it felt great. He tried to lead my hand to the outside of his own pants, and when he did that, I just said, "You know. Let's not do that, but I don't have to go home right now. It's super late. We can just go to bed and I'll hop in a cab to my house in the morning."

 

After that, he kind of jumped into gentleman mode. He even asked me if it was okay for him to sleep in the bed with me rather than on the couch...as if that was something I had implied. And then he asked if it was okay for him to sleep in his boxers instead of his jeans. We snuggled up and slept in each other's arms comfortably through the night, and then when we woke up, he got dressed and walked with me to search for a cab in the morning rush traffic. In a swift wave of the cab and a kiss on the cheek, I was off to grab my bags and head to the airport for a trip I had planned last week.

 

We had fun, and the evening was great, but now we're back to quiet. He responded to a text I sent him while I was away, because I randomly met some mutual friends of his at a bar while on my trip. And then he randomly started following me on Instagram yesterday.

 

Other than that, no contact.

 

It's a bummer. Something is holding him back, and that's okay, but I really hope I didn't just let our evening ruin our friendship.

 

Should I say something to him at some point? If so, what and when? Or should I just keep my distance and hope he comes around either for a 3rd date or just to rekindle our formerly platonic relationship? Thoughts?

 

 

I think you should hold back on saying something, a few more dates and then you might have a clearer view of where it is going....

 

 

when a guy says you are so sexy and i want to make you feel good in the same sentence after putting his hand up your skirt,to me intones a sexual relationship, if a guy tried to put his hand up my dress on a first kinda date, he better have head gear on......friend or not.......kidding....maybe not.....most guys dont do that to me if they are my friend in the first place...one reason why i date in the friend zone..a kiss on a first date, a hug even an extended one...i think is cool....if you are not up for a fwb i think you make it clear from the onset...it will be hard to go back to platonic.....if you take that step....i wish you the best...deb

[SJC2008]

It's a bummer. Something is holding him back, and that's okay, but I really hope I didn't just let our evening ruin our friendship.

 

Both of you are holding your own selves and eachother back. Yall are being incongruent. A simple "Not yet" would of done instead of implying yo don't want to ruin yalls friendship. IMO that's why he said yall can keep it casual. All in all, You are both afraid to ruin a friendship, TALK about that and make a pact that if things go south you'll still be friends after "recovering". If it's an awkward situation that you've never been in (freind to bf) say it. It's better to voice SOMETHING than nothing and leave everything up to speculation. The same applies to him.

[2013k]

Ok. So if you think we are both holding back...should I take a proactive approach and say something to him? If so, what do I say? And when do I say it?

[chrisftw]

regular means of courting don't really apply in friendships that go so deep. and 5+ years i'd say is kinda deep.

 

sometimes friends transitioning into something more will typically not think of not calling you back or picking up ALL your calls as anything negative. however they will usually call back a day later or the next morning.

 

hell my last LTR we dated for like 2 years we were best friends for 6 years. she would constantly not answer calls or call me back when she said she would. i never stressed about it because i knew that at some point i would talk to her again. and it went on like that for so long. we would flake on each other as well. it was only when a friend of her's that died in a car accident who was younger than her that made her confess her feelings towards me that she actually had for a very long time. and she didn't want to go another day without me knowing how she felt because she could have easily been in the car as well.

 

although i never was in the friendzone with her. because she would compliment my looks how a dressed once in a blue moon. and we casually flirted almost every interaction we had for 6 years. i just didn't realize how much i wanted her until like year 5.

[2013k]

CaptJack- I think you might be right.

 

On the one hand, I know my friend suffers from some major anxiety issues, and I've never once known him to have a girlfriend in the 5+ years we've known one another.

 

But he's also a very driven, smart, attractive guy, and I know that I'm not his only option (nor is he mine).

 

The first time we met, he asked me out on a date via Facebook, but I turned him down because I used to kind of date a friend of his. Then, in 2010, he asked me out one-on-one again, but I ignored it. And then a few months ago, back in September, he asked me out while I was dating someone else exclusively.

 

Otherwise, when we see each other out or when we've worked together on professional projects, we've been totally normal and friendly.

 

It's a weird little stalemate we've had until last week when we made out.

 

I wouldn't mind exploring more with him, but I guess you can't force things. He's asked me out one-on-one 5 times before, two of which we've actually gone out...If he has any feelings for me, I'm sure he'll get over the anxiety and approach me again.

 

In the meantime, how do I go about getting back to normal? Like I told him last week, I never want to be in a situation where I can't go enjoy watching his band play...It sounds silly, but I liked his music before I ever met him. And we're in the same industry, so we've come in handy for one another professionally over the years. I just really don't want to let our little moment of fun mess up both a good friendship and a great business tie. It's not like we've caused any sort of big rift, but there's a fine line between me contacting him as a friend or over business stuff versus me contacting him because I'm pushing for more romantically.