Every week, Mallory Ortberg answers additional questions from readers, just for Slate Plus members.
Q. Boyfriend’s racist, misogynistic friends: My wonderful boyfriend of a little over year came with a group of intolerable friends. I’m talking homophobia (“gay” is their favorite insult), misogynistic (an all-boys text group where they talk disrespectfully about their wives), and racist. They even had a party where someone came in blackface as an “African rape victim” and took photos of her being fake assaulted. To boot, they're bullies and the guys love to get belligerently drunk and start bar fights.
In the last few months, my boyfriend has cut off that group for those reasons—but he was best friends with them for 16 years! I’m a queer, feminist activist and he shares my politics and loves me immensely, but how do I trust someone who was best friends with people like that for so long? He says he was lonely and struggling after his mom’s premature death in college and latched onto the first group that welcomed him. But 16 years with people who are against gay marriage and adoption and defend colonialism? Help.
A: It’s great that your boyfriend has decided to cut ties with these guys, but if I were in your situation, I can’t imagine staying with him. It took him 16 years—and, I’m guessing, no small amount of encouragement from you—to decide that the kind of men who think being gay is the worst thing a person can be, who think of dressing up as “African rape victims” and pantomiming sexual assault, weren’t the kind of people he wanted to keep close to his heart. That’s 16 long years of not saying anything, since it doesn’t sound like he has a long history of challenging those beliefs. Losing your mother at a young age is difficult, but it doesn’t make racism, misogyny, drunken belligerence, or homophobia OK. Neither does loneliness. We all get lonely; that’s not a good reason to give blackface a pass.
That’s not to say he’s a terrible and irredeemable person, nor does it mean that you should only date people with perfect, unblemished personal histories. But if I were in your shoes, I’d ask myself: Does this guy have a history of standing up to racist, sexist, homophobic behavior, even when it’s difficult or uncomfortable to do so? Am I impressed with his courage and character as he displays it in his personal life, not just in theory? Does he generally cultivate friendships with people I respect and want to spend more time with? Does he have a strong sense of self that I admire? Does he have any remaining friends now that he’s cut off contact with the active racists? If you find something you can work with in the answers to those questions, then great! You might get to watch your boyfriend develop a totally different, vastly improved sort of life. If you don’t, then I think you have more than enough justification to wish him the best and look for someone else.