About eight years ago, I met a lady through work and we became friends, with our friendship continuing after she moved on to a different job. I’m a 52-year-old straight guy from Australia, 29 years married. If he’s into the idea, offer to be his first customer. You’re young and hot-you could probably make more money selling used underwear or sweaty tanks.” Then follow his lead: If he’s disgusted by the suggestion, drop it.
You can approach it indirectly by saying something like “So sorry to hear you’re selling off your music equipment. But you risk losing this guy as a friend if you broach the subject. It’s perfectly legal to buy and sell used underwear, LOSS, so there’s no legal risk. Is it legal to buy someone’s underwear? He’s a sweet guy, and I don’t want to freak him out by asking something so personal. I would love to have some sweaty clothes of his, namely his underwear, but I’d settle for a sweaty tank top. I know he needs money, as he hasn’t found a job yet and has resorted to selling off old music equipment. He’s had to drop out of college and return home. I’ve become friends with a 21-year-old straight guy.
