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For guys who are able to get girlfriends?

I should start off by saying that I have never had a girlfriend or any real relationship with a girl. Right now I am sick and tired of seeing my friends getting married or with their girlfriends. I have been solo all my life and it is like I want that same happiness and the problems that come with it. It is sucks to be sitting here by myself wondering what it must feel like to have someone to call or talk to when your lonely or listening to how your girls day went. I must sound like a damn romance movie. Okay well I know it really is not all fun and roses, but man it beats sitting here looking around just whistling to myself not knowing what to say or approach a girl and move from there. I do get dates, I should say even though I think my last one was over a year ago and just got rejected by a lot of girls. Speaking about rejected I tend to hear a lot from my family that I give up to easily on a girl, that I should keep going after a girl (in a non stalkerish way). Then comes in the voice that says how do I know she even really likes me.

The next part is the actual date part, when I am out with a girl it gets very nerve wrecking to actually, "push the envelope" and try and a make a move. I have no idea of how to break the touch barrier, move in for a kiss. All in all I don't know have any idea of how to flirt and show a girl that yes I am interested in you and want to push things further then just being friends I want more.

This is where I need some advice on how to get things moving from approaching a girl to an actual relationship.
Updates:
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I should also say that I that I always have a fear of a girl cheating on me, just up and dumping me for another guy, or just straight up embarrassing me when either approaching her or going in for a kiss.
For guys who are able to get girlfriends?
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