Hi everyone! New here, got a few thoughts wandering in my head for a couple of months and if I don't ask people's opinion, I don't know what I'm going to do.
So this is the situation (beware: it is complicated).

I dated a girl (let's call her Amy) a year and a half ago and we only went on 2 dates, date ended without any kissing or anything, just dinner. Then we both went on summer vacations and didn't keep in touch after it. Once she came back we lost touch and since she didn't text me afterwards I thought she wasn't interested in me and moved on, or so thought I did. The thing is that I was crazy about her and still am but never went after her. We've had 2 random quick encounters at college and got to talk but there was an awkwardness that held me back and made me not ask her out again and act all not interested. Now there comes another problem, all her (Amy's) best friends are best friends with a girl (lets call her Mandy) I used to date before her and dated after I stopped seeing her (Amy), but never felt about her (Mandy) the same way I did about the girl I was crazy about. Good thing is that I cut all ties with Mandy and even though she was in love with me I told her to move on because it wouldn't be fair to her to love me and me not love her.

Now, it narrows down to this, Amy must think I'm a douchebag and made up her idea of me because I didn't go in for the kiss and never went after her afterwards and never showed interest. Its because I was nervous. That's the reason I was held back of not talking to her, kind of shy because I wasn't able to kiss her and be more at ease with her after 2 dates. I was 18 after all and not that good with dating. Im not currently showing any interest on Facebook or anything because she is going on with her life and Mandy and friends might also get in the picture. Another thing I didn't mention, I was at a club a few months ago and saw Amy, but we didn't talk much because when I saw her I told her what's up and she was very cold with me, then her friend came up to me and said "if you want me to make things work with you and her let me know" I said "did she ask you to come and ask me that?" and she said "no, she doesnt know" (I then thought she wasn't honest because probably Amy had asked her to ask me that to see if I'd admit ever liking her).

I guess I deserve this but I need help because I'm losing sleep on this. Whenever I am with some other girl I say to myself, what's Amy up to. I screwed up bigtime. I just need help from someone to tell me what to do. Ask her to go for a coffee? Problems might start because of friends or she might say no and then ill lose more confidence. Her friends might influence that I am an *** also because I broke Mandy's heart. Probably she has a life on her own now with a new boyfriend and all. But she doesn't know how nice id treat her. Thanks but help me please.

Well if I went on a date with a guy and he didn't show any interest at the end looking for a good night kiss I would think he wasn't interested, maybe you should just email her on Facebook explaining that you were nervous and stuff, she will find it sweet I'm sure and then you can ask her out again, chances are she is going to tell her friends you asked her out but that's what girls are like, she might say yes or no but at least you will know!

Quote:

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she might say no and then ill lose more confidence

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Damned if you do, damned if you don't. Stress over what ifs and go crazy, or sacrifice your confidence for possible rejection.

I go for the latter because rejection doesn't shake my confidence. Just never took it personally, and there was always other options, and opportunities for fun, and romance.

But since you are backed in the corner between misery and fear, choose your poison. I mean you are already tripping from doing nothing, how much worse can rejection be? Call her and ask her to coffee. At least you did something, and rejection doesn't have to be a confidence shaker, at least not a permanent one.

Agree with Tal here. (Seems like a natural thing to do... :))

She went out with you on two occasions in the past so there was interest. Like Tal said... go for it, the ball is definitely in your court do something with it or get penalized.

You have nothing to loose by asking her out; she goes, you date, you are happy. She refuses, maybe tells you why and then you know and can move forward with your life.

Stringer

I agree with the above posts. Just be honest when you ask her out. Explain that you didn't know after the 2 previous dates if she was interested or not, but you just can't get her off your mind. That way she knows right from the beginning that you didn't pursue any further dates at that time due to being uncertain!

Tal is right that you are just going to man up and take the chance!!

Take care

Think of rejection as win win situation, you might get the girl but if you don't you will also have a new found confidence, when you see its not so bad being told no that fear will be gone! :)

I don't understand why you hesitate. What are you afraid of. Simply call her up, as her if she'd be interested in going out for dinner, and see what she says.

That the girl's girlfriend was a messenger to drop a VERY large hint (think about that- the girl you are interested in, is obviously looking to connect with you somehow), I would say your chances are better than not, that she will reciprocate.

If you don't make a move, you will never know.