I [27m] am 6"1/170lbs, and a 6/10 face wise. I have a university education, good career, car, property in my name, and I play the guitar. I speak French fluently and love movies/shows/video games and reading. I am introverted but have many male & female friends.

I feel like I'd be a great catch for many women, but I have no confidence in myself. When I am around a woman I'm interested in I often think things like "why would she want a quiet skinny office worker nerd like me when she could date some loud muscular dude who loves to take his truck out in the mud on weekends or go fishing". Weird thought I know, but I live in a rural town and the attractive guys I've seen with hot girlfriends all seem to do that sort of thing.

Cold approaching women I will often find myself running out of things to say or the conversation flows awkwardly. I oftentimes cringe myself to sleep thinking about awkward approaches I've done in my life. I have poor luck using online dating and when I do go on dates I usually get ghosted or get the "I didn't feel a connection" text afterwards. If I know the woman somewhat it usually flows better and I'm able to be more funny and get her to laugh. However it takes time for me to get to that point with someone. Approaching strangers I also often feel like I'm bothering them/making them uncomfortable so I'll usually cut the interaction short before getting a number.

I've been called a people pleaser/nice guy and also clingy. I grew up in an abusive household and was bullied in school and as a result I've usually done everything I can to avoid upsetting people or putting myself in socially hostile situations to avoid discomfort. I take medications for anxiety. I feel like I only really act like my "true" self around my close friends, and that is a confident and hilarious guy. I'm not sure if I should be trying to be that guy with women I don't know (I don't want to put them off) so I usually err on the side of caution.

How do I start believing in myself and that I am able to be desirable to women? Does anyone have any tips on how to better approach women?