This is a tricky one!

[josh03]

Hey guys so here goes:

 

So there is this girl (isn't there always?) and I have known her for several years. When we first got to know each other we dated for a months (this was the last year of high school) and ultimately broke up pretty much because we were immature and didn't know what we wanted, and both had just gotten out of bad relationships. I really liked her and after graduating I dropped off the face of the earth from that group of friends because I couldn't stand seeing her. About a year later, she started going to the same school and we came into contact again. We started talking again and pretty soon we hit it off. I had a girlfriend at the time, but we ended up breaking up. Soon after this girl and I started to become very good friends. 6 months later, I told her how I felt and made an ass of myself. When she said she did not want to be more than friends I did not take it well. Later that day, I apologized and we talked and within a few weeks all awkwardness went away and we kept being friends.

 

In the last year and half we have become closer and closer friends. She tells me about the guys that she likes and I tell her about the girls that I like and so on. I have had other girlfriends during this time (note: she never seems to like any of them) Its gotten to the point where we almost know each other too well! We are always texting and talking and hanging out. We can talk for hours. We make plans to go away just the two of us on road trips and kinda ditch our group of friends to hang out just the two of us. Everyone that knows us both asks "Why are you two not dating?" So for the last year and a half I kinda go in and out of denial about how much I like her. A couple of months ago we were talking and I brought up how I used to like her and she mentioned that she was actually on the fence about whether we should be more. (So i kinda screwed it up then, great)

 

I am kinda known for being kind of a ladies man. Not a player, just good with girls and that kind of thing, because I learned to play games. But I realized that is not the right way to go about it and just want to be myself. So I decided to take a break from girls. She knows this about me, she is the one girl that I cannot lie to and just reads me like an open book. A few months into this is when I started to realize how awesome this girl really is, we get along just being ourselves with each other, its something that we both have expressed we really like about our friendship.

 

We are becoming each other's closest friends and I think there could be something more and awesome there. From the things that she says (aka, sometimes even she and I question if we are dating and don't realize it) and some things her friend has let slip, I can tell the thought has crossed her mind recently. I'm not sure what she thinks about it. I think she thinks that there could be a spark there, but that she is afraid to lose one of her closest friends (as am I, but I want to take the risk because I think what we have could be much more) Also, knowing her the fact that she is moving away in a year or so turns her off to the thought of something that could actually get serious. But I wouldn't go for this if I didn't think we could make it work with medium periods of long distance.

 

This is something that I want to pursue, because its not everyday that either of us meets people that get along as well as we do. But I am not sure how to determine how she feels about it, and what the best way to bring this up to her in order to not have her feel pressured or shocked. I would note that she knows me well enough to know if I like her, so my guess would be that if were planning on bringing it up, she would see it coming a mile away. What do you think?

[USMCHokie]

This is not tricky at all.

 

You allowed this situation to happen. You settled for being her friend even after she said she didn't want to date you. You allowed yourself to "pseudo-date" her all this time. You allowed her to have her cake and eat it too. For all you know, you could have been banging dudes on the side while you were being her best friend.

 

Bottom line: Don't be best friends with a girl you want to date.

 

You really have only two courses of action here:

 

(1) Grow some balls and ask her on a bona fide date that establishes that you want to be in a relationship with her. Stop p*ssyfooting around and make it crystal clear what you want.

 

(2) Stay being her "best friend" and stop whining about wanting more.

[josh03]

This is not tricky at all.

 

You allowed this situation to happen. You settled for being her friend even after she said she didn't want to date you. You allowed yourself to "pseudo-date" her all this time. You allowed her to have her cake and eat it too. For all you know, you could have been banging dudes on the side while you were being her best friend.

 

Bottom line: Don't be best friends with a girl you want to date.

 

You really have only two courses of action here:

 

(1) Grow some balls and ask her on a bona fide date that establishes that you want to be in a relationship with her. Stop p*ssyfooting around and make it crystal clear what you want.

 

(2) Stay being her "best friend" and stop whining about wanting more.

 

Sounds about right. Just gotta do it.

Edited April 29, 2012 by josh03