I’ve had a very close friendship with a woman who works for the same trucking company I do. I am 15 years older than she is and am self-conscious about our age difference. I don’t want to be That Guy who hits on younger girls. But I really like her and would like to step things up. I think she would, too, but we both get tired of hearing all the jokes about how I’m robbing the cradle and am a dirty old man.
What do you think? She’s 25, I’m 40 and we are both single.
I think you are confusing That Guy with the one who hits on younger women while he’s already married. Which is not to be confused with actually “dating.” You want to date this young thang, and she wants to date you. Come back when you have a real problem. Like when she’s getting hit on by guys her own age and you feel insecure and anxious about it. I’ll be waiting.
I’m just say’n,