Is there a way to not be a jerk when you hate your boyfriend’s friends? My boyfriend is great, but he is friends with some complete degenerates. I don’t really understand it but it has something to do with their history and loyalty because of what they’ve been through together. I’m not like making a huge deal out of nothing; it’s not like his friends are just annoying and I’m complaining. Last week, we were all hanging out and one of them was bragging about how funny it is to cheat on his girlfriend. I don’t want to be around them. I don’t want hating his friends to get between us either. I don’t think I’m asking him to choose.

Any advice I’m going to give is going to hinge on how much work you want to put into this. The easy response is to just say that he has his friends, you have your friends, and its fine to keep them separate. I mean, I’m assuming that’s how people who are high up in the Republican party manage to stay married to people who are high up in the Democratic party.

If that’s sufficient for you, then go forth. There’s nothing about telling your boyfriend that you’re not into hanging out with his friends that makes you a jerk, unless you put an ultimatum in there that makes him choose between them and you without providing for any chance for people to have a conversation about the problems you’re seeing.*

The key here is that you have to be okay with your boyfriend hanging out with them when you aren’t there. If he only sees these folks once every month or two, then it’s likely not to be that big of an issue. If, however, this friend groups gets together every weekend and sometimes during the week, then you’ll need to talk about what makes sense in terms of how you both spend your time.

Still here? Okay, here’s the deal: if this is going to be a longer-term relationship, then there are some real questions here that can’t be easily answered on a website and deserve some examination:

1. Why does your boyfriend choose to remain friends with people that are so problematic?
2. Would you choose to stay in a relationship with someone who maybe doesn’t see anything wrong with the things that are clearly so objectionable to you?

Let’s look at your boyfriend first, and the general idea of maintaining friendships when there is some deeper level of disagreement about values. While it is entirely possible that your boyfriend shares the opinions of his friends, and just uses the ‘history and loyalty’ argument to rationalize it to himself and others, let’s assume that you and your boyfriend do share the same concepts of right and wrong.

My sense is that perhaps you have a different (or perhaps stronger) idea of what those values look like out in the world, and hold those you spend time with to that standard. This isn’t then a disagreement about values, but about how we live our lives authentically given these values.

I think the only way to sort this out is to talk to your boyfriend to get more of his perspective beyond “we’ve known each other forever and seen some shit together.” Do you think he’d be open to listening to your thoughts on why you find his friends so problematic? I hope so. You can start with something like “Hey, can we talk a little bit about Brad? I know you guys have a history; I’m wondering, has he always made comments like he did today? What he said made me uncomfortable, and I’m wondering if you noticed it.”

This way you’re opening up the conversation and allowing your boyfriend to offer his perspective. Through talking to you he might come to realize that perhaps these friendships don’t match with the values he holds, or that he’s interested in talking to his friends more about the things they’ve said and done.

He might also get defensive and accuse you of trying to come between him and his friends. And in fairness, you kind of are, in a roundabout way. That’s not a jerk move, though; it’s part of figuring out how to navigate a relationship. You are pointing out things that perhaps your boyfriend has chosen to ignore, and making it harder for him to continue to do so. That’s rough, but sometimes other people see things that we have missed, and it can sting to realize that.

Once you’ve had this conversation, the next time your boyfriend asks you to hang out with him and his friends, consider telling him that given what you’ve shared, you’re not interested but that he should go, and then use that time to do something that you’d rather do, like get a teeth cleaning.

But this brings me back to the question about you and your relationship goals. Are you cool with being in a relationships with someone who is willing to overlook things like racism or misogyny in his friends, even as he disavows them in his own life? How far removed from problematic actions is far enough for you to write it off or ignore it? Is your boyfriend staying friends with these guys a demonstration of what he values in life, and does that mesh with what matters to you? (See, I said we needed to get a little deep here).

Look, we don’t get to create actual bubbles to shield ourselves from all the things we don’t like. And those of us with some measure of privilege in the world have, I believe, a duty to have the uncomfortable conversations with people who might be more willing to listen to us than those who are directly harmed by their words and actions. But there is a balance here, and you do get a say in how you want to spend your free time, how to live in alignment with your values, and what relationships you are interested in nurturing.

*Unless abuse is involved. That never requires you to stick it out and try to find common ground.