Dear Prudence,
My friend, Lana, is a good person but a bit of a train wreck when it comes to romantic relationships. She cheated on one boyfriend with her married boss, wrecked the car of another boyfriend, and then refused to pay for repairs, and her insecurities and jealousy ruined her last relationship. Despite these bad relationships, Lana has been a supportive friend—she was there for me when I was going through chemo, cooking me meals, and giving me rides—and she’s a witty, funny person.
But all of her worst qualities come out when she has a boyfriend. It’s like a romantic Dr. Jekyll and Mr. Hyde. As a result, Lana is single again. Recently, I invited Lana to a party and she started talking to a co-worker of mine who I’d also invited to the party, Rob. They both seemed to hit it off and exchanged numbers, but now I’m terrified that Lana will do something embarrassing or awful to Rob. Should I give Rob a heads -up about Lana’s past behavior or keep my mouth shut? He is a really nice guy and I fear if something goes wrong, he’ll be upset that I didn’t warn him. On the other hand, I don’t want to betray my friend by gossiping about her and who knows, maybe this time it’ll be true love.
—Can’t Trust My Friend