Dear Prudence,
My friend “Bailey” has been dating her boyfriend “Justin” long-distance for nearly five months. I’ve never met him, but she showed me some pictures. He seemed vaguely familiar, but I put it down to the fact that he was from my former city. Recently, she went on a trip to see him and when I saw the Instagram photos they took together, it clicked. He’s grown a beard and has been going by his middle name since I worked for him, but some LinkedIn searching confirmed: Justin’s famous in my field for underpaying/never paying freelancers.
Justin had such a rep that when I took a gig for him (I was desperate) nearly 10 years ago, I had to carefully structure my work so the most crucial piece came last and was contingent on 95 percent of the fee being paid already. Despite that, Justin still tried to write a bad check, only returning my calls when it became clear that his project couldn’t move forward at all unless he paid me and could get that last bit of the work. We parted on bad terms, but nearly everyone in that city’s freelance network had stories about him. His startup folded, and he appears to be working under someone else now. I hope the oversight is keeping him honest.
He is a red flag, but I don’t know how to tell Bailey. She’s always faced a lot of criticism about even her great boyfriends from her family, so she’s hypersensitive to this stuff. And I didn’t recognize him until recently, which will also make it awkward. But where do I start?
—I Have Literal Receipts