One of my closest guy friends (I’m a woman) recently went through a divorce. He and his ex had been together since college (we’re now in our 30s) and I have somehow become his “back on the scene” confidante. I have no idea why—maybe because I was single for a lot of our 20s? My friend is average-to-attractive, so the odds are super in his favor because NYC has a shortage of decent guys, it often seems. The problem is that he is acting like he’s still 19. Or not even him at 19 because we were all big nerds, but some stereotype of a frat boy. It’s really weird and it makes me very uncomfortable. He rates women on a 1–10 scale with no irony, he talks about his “game,” he brags about being super great at sex (I know his ex well, and she says he’s average at best). He’s not acting like the person I’ve known all these years and I don’t really know how to call him on it. Like, I’m glad he’s getting out there, sleeping around, doing all the stuff he feels like he missed out on, but he doesn’t have to act like an ass about it. When I’ve tried to gently point out when he’s being a dick, he shrugs it off. What should I do here?
So there are two possibilities here: One, that this is the guy he’s always been, but somehow his ex kept it in check and he never felt free to let his asshole flag fly. Or two, he’s going through some kind of weird phase he will be super embarrassed about later.
Either way, if he’s making you uncomfortable, you don’t have to continue to be his sex diary. Just say, “Dude, that’s not really something you need to share with me,” and keep cutting him off when he overshares. If he pushes it, it’s 100 percent within your friendship rights to put as much space between you two as you need. Supporting a friend through a divorce is part of being a good friend, but listening to a dude go on about how some actual human being is a “7.5 face, solid 8 body” is not.
If you think this is just how he is from now on, I would go ahead and move on. It sucks to lose a friend that old, but it also sucks to be friends with someone who is an asshole. My gut says that this is just a phase, though, and maybe worth seeing through. You mentioned that you’re still friends with his ex: Could this all be information he’s hoping get back to her through the grapevine?
Or maybe he fell down some kind of Internet hole into a pickup artist kind of forum and this is just what he thinks people do now? Or he’s insecure about his lack of knowledge about how non-college students get together, and that’s manifesting as some kind of late-onset frat bro? Maybe you need to stop being gentle: Take him out for beers and really lay it out for him that he is being gross and weird, and that he’s going to ultimately lose friends and potential cool women to date acting like that. Tell him what women actually like. Breakups do weird things to people, sometimes. Good luck. You sound like a good friend.