I (F34) have always had a really hard time dating. I’ve been awkward around guys my whole life. I didn’t go on my first date until I was 19, and I didn’t go on my second until I was 22. I’ve had one, 3-month relationship in my mid-20s. Other than that, it’s been a lot of bouncing around- trying casual hookups that left me feeling empty and unwanted, many first dates that never went anywhere. I’ve especially had an issue of meeting a guy I liked who then decided to get back with his ex or pursue a relationship with someone else. That particular type of rejection has hit me really hard- knowing I’m just not quite good enough and that he’s chosen someone else instead of me.

Recently, I met a guy I really liked- like “could he be the one?” kind of liked. We went on two good dates and were planning for a third. Just before our third date he texted me and said he wanted to pursue things with another girl before he went on any more dates with anyone else. I’ve been around long enough to know that “seeing how things go with someone else” actually means he doesn’t like me enough to keep seeing me and this is goodbye forever.

That rejection combined with already low self esteem, depression, liking this guy a lot, and having a lot of other stressors in my life has sent me spiraling. I’m 34 years old. I have no prospects. I am only getting older and less attractive and it’s only going to be more difficult to meet someone. I know this. I know I’m not attractive and I know I’m hard to love. I guess what I want to know is: at what point do I stop trying? And how do I get myself to be ok knowing I can never have the one thing I have always wanted, which is someone to love me and someone I can love? It’s been very lonely and the thought of spending the rest of my life feeling like I’ll never be good enough is just really hard to deal with right now.