I've had an unhealthy relationship with my self-image for the longest – I put a lot of effort into my appearance, and I genuinely like my appearance most days. Every time I go out to a bar/club, I get complimented or hit on, plenty of stares that are often uncomfortably long, free stuff, etc. In casual settings, it happens less, but it does happen frequently. In work settings, my coworkers have called me pretty and have made jokes about "what they'd give to be a pretty young girl" and so on. However, I grew up being told I was ugly all the time, so hearing people tell me I'm pretty feels like everyone is lying to me or trying to make me feel better, even strangers and people who gain nothing from complimenting my appearance.
I genuinely feel as though most people I want to talk to will find me hideous and off-putting. I have terrible self-esteem, and it prevents me from doing simple things like making eye contact with guys I find attractive, much less learning how to flirt and engage. I also think maybe my personality is off-putting, considering how fast guys lose interest.
All I ever wanted was to be "pretty," but now that I am considered pretty (I think), I still feel the same and like I have the same luck. I'd love to connect with people more, but every time I put myself out there, I feel needy and desperate, and everyone can tell. I compare myself constantly to friends who sleep/date around a lot, thinking that there must be something wrong with me or that if I were prettier, I'd have their opportunities. It also feels like I am the only 22-year-old woman who struggles with this stuff, though I know that's not true.
Just looking for advice. I'd also like to find my "style" of flirting as well; the singular thing that I find that works is my humour – I like to tease and be lightheartedly sarcastic, or challenge them on an interest (e.g., I play video games and I'll "insult" their choice of game even if I enjoy that game myself). I always choose something I strongly believe they wouldn't be insecure about, but I'm terrified to do that with a guy I actually like/am interested in, in case it doesn't land well, which on occasion it indeed doesn't.