@ragingloner what's up bro. I recognize your username from another board now. We've actually exchanged pm's cuz you reached out to me for help and I tried to give you some advice.
So I'll do it again here. Unless you're fucking piss broke try to aim higher than the $40 spots or these women on Roosevelt Avenue. I understand not everyone here makes the same amount of $$$$, but I know you're a young dude. Put some effort into trying to date some girls your age. With all the dating apps out there now it's easier than ever to meet women. If you continue to do what you're doing a whole lotta your life is gonna pass you by, bro.
I'm telling you this (again) cuz I'm trying to look out for you. It seems you didn't take my advice before, and you most likely won't take it now, but maybe someone else reading this who is around your age and in a similar situation, will.
Happy to continue this conversation further if you want to. Just pm me.