Hi all. I’m 42. Never married. I own my own business, grad school degree, and maybe don’t know or appreciate my value. I’m painfully tired of being single and find it impossible to meet women. I used to not have so much trouble, but I’ve never been a natural or any sort of ladies man.

A few years ago I rage quit a job and have been paying for it ever since. I feel like I work all the time only to service large debt that overwhelms me. I’ve gotten out of shape as well, probably owing to depression and emotional eating.

Regardless, I’m terrified I’m never going to meet anyone, or anyone good. I’ve tried online and the only contacts I make are fat ugly older women. I have a friend in the same building as I/same career field, who is a struggling alcoholic, bipolar diagnosed, divorcee with a terrible home life.....with cute dates all the time. He has hair and I’m shaved bald, but aside from that, I don’t get it. Recently a friend of mine suggested I consider dating women “like her.” She’s 52 (and married anyway) and just.....ugh.....no thanks. But I also felt like a jerk just being like that. I’m always being “set up” and then the girl is just not cute at all. I don’t need Jennifer Lawrence....but come on.

I’m in a place where I need help. And I don’t know where to begin. I really don’t want to compare myself to others but it’s very very hard to see other guys of comparable position or looks or whatever with just a cute, decent girl who presumably showed interest somewhere. And I try not to be angry but I’ve long ago only processed emotion through anger. I don’t lash out at people, but I’m cynical and I will stew. Everything just feels like I have some horrible destiny to fail and to be alone. I used to feel like I had a future but now I feel like I’m trudging through the days just waiting for it all to be over. Depressing, I know.

I badly want to turn the ship around but I also don’t know where to begin or even what small goals to set. Everything seems so far - too far - away and I tend to give up easily anymore.

Can someone coach me up here? Anything to help me begin a new way. I’m having a lot of trouble doing it myself and just don’t know where to go now. Thanks.

Greg