23M - I get stuck when I like a girl, act too "friendly", and feel like I’m stuck at 0% progress. Advice?

Hi everyone,

I’m a 23M and I have a lot of trouble dating. It never seems to go the right way. I’m starting to think that I will never be able to get a girlfriend again, or at least not someone I genuinely like.

I’m a normal-looking guy—not a model, but I wouldn't call myself ugly either. I also consider myself to be quite smart. I've been training 4 times a week for some years and have a good body.

My problem is my personality. When I'm with a girl I actually like, I get completely stuck. I can't keep the conversation going, and I find it really hard to express myself, my feelings, or to give compliments. Ironically, I could talk for hours with strangers if I have no romantic interest in them. Lately, I've had zero luck with any girl I've tried to approach.

The reason I'm writing this is that I honestly feel like I never know what to do.

A few days ago, I went out with some friends and my flatmate (20F). I noticed her energy completely shift when she was talking to me compared to two other guys. As soon as she started talking to another guy, she was smiling, laughing, and becoming touchy. Later, that guy left and another one arrived—someone she'd had a previous fling with. When we got back home, they came back together and kissed right outside our door.

Later, she was telling me about what happened. I asked her what she sees in that guy, and she just said: "He knows how to take me" (he knows how to handle me). When I asked for a further explanation, she couldn't really explain it. I don't know this guy well, but from what I know, he just knows his way around girls.

I am really envious of this skill. I would love to be able to do the same, but whenever I meet someone new, all I can do is act friendly. I feel weird breaking the "friend barrier," and whenever I do try, I must be doing something wrong because it never goes well.

I’ve noticed that dating seems to be a loop: the more success you have with girls, the easier it gets to have more. Right now, I feel stuck at 0% progress and I don't know how to move forward. I know I should start talking more to girls and being more expressive, but I just can't seem to do it.

Has anyone here been through a similar experience? How did you find a way out of this?