I've been single for three years, and have spent about two months actively looking for either a relationship or at least a hookup (which isn't really what I'm looking for, but it's been three years since I've gotten laid). It's rough for a guy in his late 30s here. For example, last week I bought this cute woman a drink and started chatting her up, only to find that she's young enough to be my daughter (if I had made some stupid decisions and wasn't so awkward in high school).
Apps aren't working for me, either. I get a lot of scammers and bots. I'm still awkward as fuck, so when I find women who interest me or who match me, I don't get many replies. When I do get replies, I'll make a joke that falls flat, or otherwise be really fucking awkward, and then I get ghosted. For example, I sent a picture of Richard Nixon to one woman, and then explained that I was under the impression that unsolicited Dick pics were part of online courtship rituals. She not only ghosted me, but deleted her account on that site.
So... Any ladies here from northern Illinois or southern Wisconsin who enjoy bad puns, dad jokes, wandering aimlessly at night, and stargazing?