Dear Prudence,
Jen and I were good friends in grad school. She was a very reliable friend, though hard to really get to know. She is smart, extremely successful, and was for a long time unlucky in love. When we were still close, she started a strangely secretive, undefined, on again, off again relationship with bad boy “Raf.” A mutual friend of ours, “Carly,” was good friends and coworkers with Raf and knew his history of sex addiction, infidelity, and drug use.
During a time when Jen said she was not dating Raf, Carly slept with Raf. And at some other point, Carly’s best friend Crystal slept with him too! When Jen found out, she cut those two out, a reaction that made sense to me. She and I tried to remain friends, but we eventually grew apart.
Jen and Raf have been together in the handful of years since, with him posting last year about his newfound sobriety. But soon after, he reached out to Crystal inviting her to do coke and have sex with him! I saw the screenshots! She declined.
We found out from another friend that Jen and Raf are engaged to be married next summer. But he reached out to Crystal again this month asking to hook up and trying to sext her! She asked him if he and Jen were in an open relationship and he said, no way, she’s so straight-laced. And these were texts that he admitted the next day he didn’t remember sending. (So he’s not sober anymore, right?)
I’ve seen their social media adventures, and they genuinely look happy. I’m sure he’s totally enamored with her, but I have a terrible feeling about this! I haven’t talked to Jen since we tried to catch up in 2020 and it fell flat. There’s nothing I can do, right? Is he totally pulling a fast one here? I am so sad for her.
—Suspecting a Scoundrel