Good friends, both have history, what are the odds this will work?

[Origin]

Hello LS,

 

I have extremely good friendship with a female friend and I like her but I'm terrified of losing her as a friend if she doesn't feel the same way. Regardless I decided I'll tell her how I feel but I was wondering.

 

How often does a friendship grow into a meaningful relationship and should we in all honesty even try because we both have a past of hooking up with each other's friend?

 

I have known her for 15 years.

 

When I first met her I liked her but I was afraid to try anything with her because I hooked up with one of her friends before I meet her, I just figured she wouldn't be interested. Not long after that she got into a serious relationship.

 

So fast forward few years ahead and she becomes single at the same time as me. During that time we spoke but not a whole lot, I actually started semi-talking and seeing a girl from my work(entirely different story and I even posted that story here on LS) but me and her always stayed in touch as friends. So one day she came out to a bar where I was with a very close male friend of mine.

Long story short I introduced them and they end up dating for two years.

 

They end up breaking up around the same time I finished the situation with the girl from my work. During this time we became closer then ever before, sharing every emotion about life and talking about life problems. This wasn't any longer some goofy, joking friendship, it somehow envolved into something else.

 

So 6 months later(today) after the breakups and everything I'm noticing some changes in her towards me. I've noticed that increase probably in the last 2 months.

 

The signals are weird. There are days she talks how she wants to introduce me to a friend so we can date and then there are days where she looks crushed when I tell her I hooked up or or if I took a girl on a date. It almost feels like jealousy.

 

Even tonight, a bunch of us were at a friend's house for a boxing fight. I got an emergency phone call from my work and I had to leave in a hurry. She texted me shortly after I left and it seemed she was disappointed I left, an hour later I got a text from her that said exactly this "have fun at "work"". It seemed she didn't believe me I was going to work but maybe going to see some girl.

 

She's very aware of all the females in my life as I often asked for an advice and I'd also give her advice from a male perspective.

 

So that's that. The signals are weird, I may very well be wrong but I wanna get it off my chest. I'm gonna do it one way or another I was just asking for an advice.

 

How should I approach this? What could be the fallout if she says NO and what are the odds of meaningful relationship if she says YES?

[preraph]

I think there hasn't been a big mutual attraction or something would have happened before now even if one or both of you were dating someone. I think it's likely the friendship could deteriorate if you confess. That's usually what happens. Also if she does have some interest there don't you think she would have been real touchy with you or something? I mean women seem unable to bottle something up for very long.

 

My feeling is even if you both agreed to give it a shot, that whatever prevented you from leaning into each other for all these years will be the same thing that makes it not work long-term. Plus if you are reading her as jealous and if you are right, which there's no way of knowing, but if you are right then you have a woman who you are even dating who is jealous and though you may be viewing her potential jealousy as a positive sign, jealousy is usually just a big problem in a relationship. It usually isn't something that just happens because she's all into you or whoever but that this is just her insecurities that comes out with whoever she's with. It could be very hard to live with.

 

That said if you're willing to risk the friendship you've known each other 15 years and you should be able to have a talk about it. Good luck.

[maxi105]

just ask her,

 

you wont know what she is really thinking about you and a possible relationship with her for sure unless you talk and tell her how you feel.

 

so depending on what she says; you will know which way is probably the better to go.

 

good luck, maxi.