I’m generally a good looking guy, but for some reason I’ve had this problem all my life where, with girls, when the time comes to make the move and go for the kiss I feel incredibly awkward and often lack the balls to do it, even if I know she is into me. And after each time this has happened, it’s impacted my self esteem more and more. In my history with girls, 90% of my crushes were into me and I fucked up ONLY because I was too awkward to make the move, and only 10% were successful. It’s fucking ridiculous really, they are always into me and somehow I am always passive enough to fuck it up. Well, last Friday I was in the US on a business trip and I went partying one night. I very rarely do this, but when I party I like to go all out. So — long story short, I bought & took some drugs, lost my friend in the process (he went home cause I took too long), but the drugs gave me the confidence to approach girls solo. I found a really attractive woman and approached her a couple of times unsuccessfully, but she had a chubby friend who was more receptive. I literally just told them straight up I have drugs and wanna share them, which came on too strong initially, but at 2am the party ended and I guess they had gotten to know me enough to trust me as I passed by them on and off with brief chats throughout the night. Anyway, we go up to these girls’ car and we do the drugs. They drive me to this amazing view in the mountains out of town. And this whole time I’m just being 101% honest and myself about everything, not giving a shit (which I have NEVER been but, you know, drugs, and not caring what they think cause I’m on the other side of the world going back in 4 days). We have the most profound, amazing conversations and I’ve never felt so accepted in my life. They were Hispanic, much older than they looked (the pretty girl turned out to be 38!), they were both single moms with kids. I think there was something about the pretty one’s kids that was too much to outright share even in that state, because she described her kids as “lost souls” and it seemed really hard for her to talk about it. Anyway, we smoke some weed to the view. Eventually, as it’s cold, I give the pretty girl my jacket and hug her to warm her up, and the chubby girl leaves us. I am hugging her from behind and I can feel her rubbing up to me. As always, I did nothing. I didn’t even kiss her. I did nothing and then we got back in the car and the chubby girl wanted to go home, even though the pretty girl wanted to watch the sunrise with me. I just agreed to go home. I was tired, had work to take care of the next day, and all around I guess I’m a fucking idiot. The drive back is awkwardly quiet. I am once again the passive loser leaving the girl confused. They drove me home and I just said bye. The pretty one seemed so disappointed in me. Then when I was finally alone and reality hit me - once again, insane, insane regret. Still on drugs. I couldn’t fall asleep for the next 6 hours so my work was fucked anyway, and I was just consumed with regret. It’s been 4 days since then and I just can’t shake off this profound feeling of regret and I am feeling demotivated about everything. I have never felt this euphoria that I felt with those girls, I have never connected with someone so much in so little time. Now I’m back in Europe. I will never find this girl again. I will never see her again. Does she think about me too? It’s a vast, lonely world, and I’m a fucking loser who always misses up on his opportunities. I have craved this sexual adventure and novelty all my life, and yet I am always too big a pussy to seize the situation when the time comes. I don’t know why it’s so awkward for me to just make a move. But my life has been a history of such failures and this one — this last one really hit home. I find myself unable to move on. There is so much shit I have to do, so much time before I get another such opportunity, if ever, and I do not have the motivation to do any of it. With each such failure I add to the pile, it becomes heavier and heavier to carry this burden. Please help me cope. Tell me a nearly 40 year old hot hispanic single mom was a bad person to have sex with. Tell me she was too old for me (I’m 30). Tell me I could have gotten STDs. Tell me it wouldn’t have worked out anyway. Tell me I could have just gotten more attracted if we had sex and it’d have been even harder to move on. Tell me anything that will help me get over this, please, but please mean it. Why is it so hard for me to make the move?! submitted by /u/voidglare
Originally posted by u/voidglare on r/AskMen