Posted by The Doctor

I'm pretty sure she didn't date him just for the fun. I will admit, I had my faults when I didn't make a move, but I had every reason not to. Like I said - I'm not comfortable with doing it.

I don't want the relationship to end between them because of my stupid reason. I want them to be happy, and if she genuinely wasn't happy with me, then I somewhat understand her motives.

Right now, I told her something was going on with me (this issue), and she was willing to listen and be there for me. I am not going to tell her yet, but the fact that she's willing to help me with my problems just makes me not want to break our friendship up.

So, I think I have enough advise. Here's what I'm going to do.

1. Confront her with the problem. I will tell her that I feel uncomfortable being her wingman, and that I think the best way to keep our friendship on track is for her not to talk to me about him. If she doesn't feel like that is a valid option, then I think that friendship is over.
2. Get another girlfriend. I need to have experience, and I think the best way to do so, looking at all this thread's advise, is to find another person.

Thank you so much. I really love that there is a community out there willing to help those in need of social advise. I love all of you guys.

Yo I really like your plan. I highly doubt she will have a problem with the fact that it makes you uncomfortable and as a friend she will probably be happy that you told her.

On the contrary, getting experience dating always seems harder than it is. A good way to get a girls attention who is a stranger to you is to show off any great skills you have in a non-gloating ways. There is a coffeeshop in the downtown of where I live and the girls always droll over this quiet boy who is always sketching a masterpiece, and this other guy who loves to improvise music with strangers using his guitar skills.  

Posted by Colin

I don't think dating multiple girls really gives you "experience" everyone enjoys different things and acts different in relationships, you can never understand women and it is a scientific fact.

It totally does. There's no way anyone is completely comfortable on their first date ever, or first relationship for that matter. Especially if you are an awkward/shy person, then you really need the experience of going on more dates so it can become a normal thing for you and won't be terrifying or difficult. And if you have trouble "understanding" a woman then generally that means a lack of communication, or not being very honest with eachother, or you may be socially disabled.  

Posted by Colin

I don't think dating multiple girls really gives you "experience" everyone enjoys different things and acts different in relationships, you can never understand women and it is a scientific fact.

Disagree with this.
Girls can be very easy to understand, it just requires a certain way of thinking. There will always be the exception- but the majority of girls, while very different on the outside, think in very similar ways especially when it comes to guys.

How girls think? They want the guy that impresses everyone, leads the group, believes in himself, keeps some mystery, fights for her honor, makes other girls jealous.

Perhaps one of the biggest thing that has girls by the neck is the guys who make them feel like it is a special occasion when they are around. Nothing will make a girl start to get bored and lose the spark more than opening all up to her and always trying to hang out with her