How to Deal With the ‘Ally’ in Your Friend Group Who's Actually a Huge Jerk

Over the past few years, I’ve had a lot of separate conversations with friends and co-workers about the misogynists in our friend groups. Rarely is it the overt, ridiculously horny Mad Men–esque sexism we were raised to reject. Instead, it’s coming from the self-professed allies who know better than to call women bitches… so they either do it “ironically,” or wrap their complaints in enough theoretical feminism, good politics, and self-deprecation to convince everyone they are different. I don’t know if this is better or worse than the cartoonishly retrograde stuff, but it’s certainly exhausting. 

So often, the red flags begin waving in conversations about dating. Maybe it’s a lot of casual references to “crazy” exes, or the way they hit on literally all of your friends. Perhaps they refuse to do any self-reflection—e.g., “What about me might be putting potential romantic partners off?” “Do the people I’m physically attracted to seem to actually share my values, and how is that affecting my relationships?”—when things don’t work out.  

Maybe they perform self-awareness with regard to misogyny, but don’t actually ever seem to change their shitty behavior, or they claim to want to date someone smart, but sure do get defensive when said smart women have strong opinions that are different from their own, or when women criticize them in general. Or perhaps the instances in which they acknowledge their own privilege or say they “just really want to meet someone smart and settle down” are well matched by the amount of inscrutable “jokes” they make that seem, upon further inspection, not terribly funny and definitely kind of sexist.  

The reality that seemingly “woke,” seemingly nice people can also be misogynists is fairly well-established, but that doesn’t make it any easier to deal with when it’s happening in your friend group. If you have the nagging feeling that someone you know is not actually the feminist they claim to be and you aren’t sure how to deal, here are some things to try. 

In the past couple of years, irony has replaced sarcasm as the most irritating stand-in for an actual sense of humor. “Ironic” sexist comments are particularly insidious, and are often difficult to shut down, because it’s not always clear how serious the person is—which is, I suspect, the whole point. Most of us don’t want to look uptight or like we can’t take a joke, and that fear is what keeps us from calling out bad behavior that could, I guess (?), be viewed by some people as funny.

In a 2017 essay about ironic sexism for The Lifted Brow that is absolutely worth your time, Emma Pitman writes that, “irony doesn’t negate sexism, it just helps it dodge accountability.” Later, she continues: “Ironic sexism will always bring you to a frustrating, paradoxical junction, because hipster culture mocks earnestness and it takes earnestness to call this stuff out. … Instead of valorising earnestness in the abstract, I’ll get literal and make the vulnerable, uncool admission that ironic sexism hurts me.” 

When someone claims they obviously meant what they said ironically—the 2020 equivalent of “lighten up, tits” from people who know better than to say “lighten up, tits”—you don’t have to accept that as fact and let them off the hook, particularly if they do other things that leave you wondering about their intentions. Instead of deferring to their judgment about what counts as a joke, trust your gut, and recognize comments designed to test the waters for what they are. Be willing to be the person who says, “Did you mean it ironically, though???” or “I actually don’t find that funny.” 

Being pro-choice, “Yasss queen”-ing Kamala Harris and Elizabeth Warren, having lots of female friends, and not actively trying to make the lives of queer people a living hell is good and fine… but it’s possible to do all of those things and also treat women badly in your personal life, at work, online, etc. Having a daughter and a wife and being well-versed in the writing of Audre Lorde doesn’t make you a good person. You know this! I know you know this! 

But I also know how easy it is to brush aside behavior that doesn’t sit right with you because you’re starting from the place of “well of course my friend couldn’t possibly be bad.” The thing is… they can. If you’re viewing someone’s stated progressive values or friendships with smart, thoughtful people as the end-all, be-all, remember that in reality, they might not actually be listening to those people, or treating them particularly well… and no one is challenging them, much in the way you don’t want to at this very moment, because it’s a difficult thing to do. Instead of being the smart, thoughtful person who unintentionally puts a shiny gloss on their bad behavior, be the one who is willing to hold them accountable for it.

If you’ve fallen into the habit of smiling and nodding whenever your friend tells you a story about their recent argument with their girlfriend or the latest female co-worker who they insist is “dumb” and “angry all the time,” it’s time to look alive. Start listening a little more closely to what they are actually saying, and make a point to participate more actively. What kind of patterns are you seeing? What do you think is actually going on? How would this sound if it were told in an r/relationships or r/AITA post? 

If something is pinging as off, or you’re beginning to think your friend is maaaaaybe not the most reliable narrator, start asking more direct questions, and be willing to share your opinions with your friend. That might sound like: 

• “Hm, I don’t think it’s totally fair to say she’s acting ‘crazy’ or putting too much pressure on you. If I was dating someone who did [thing they just described doing], I’d be pretty upset too.”
• “I’m not sure what you’re describing is her leading you on, to be honest… it just seems like friendly behavior to me.”
• “Hm, have you asked her what she [wants/thinks/needs]?”
• “I mean, it kind of seems like she’s doing [thing they don’t like] because you’re doing [thing they think is totally fine and not a problem at all].”
• “Dude, what you’re describing is really [intense/over-the-top] behavior on your part, and I’d be [creeped out/pissed/annoyed/not returning your calls] if I were her too.”
• “Hmm, I don’t think the situation is actually that confusing, to be honest… it kind of sounds like she’s just not that into you.”

Try to say all of these things with a measured, non-judgmental, open, and curious tone—this person is your friend, after all, and the point isn’t to shame them, but to have an actual productive conversation. As therapist Ryan Howes told me when I was interviewing him for my book last year, “As a friend, it’s important to step in because people can be so unaware of what they’re doing. A big part of our job as friends in any relationship is to hold a mirror up sometimes and say, ‘Here’s what I’m seeing right now. I could be wrong, but it seems like this might be going on.’” And how they react when you do that will tell you a lot. 

People who say and do overtly shitty things are often counting on the fact that you’ll be too polite or unwilling to be seen as overreacting to call them on it. Responding immediately in a way that unambiguously communicates “Wow, that sucks” to your friend—and to anyone else who is present—is similar to a referee blowing a whistle; it’s a quick, sharp way to get everyone to pause for a second and take a closer look at what just happened. 

Some options: 

• “I’m sorry, what?” followed by, “Are you saying that [what they are implying, in plainer terms]?” 
• “What do you mean by that?”—a good option if you’re not 100 percent sure that they are saying the awful thing it seems like they are saying.
• “Yikes” or “Ouch”—good for when your head is about to explode and you need a moment to collect your thoughts. 
• [No verbal response, just a face that very clearly connotes “wow, what a deeply not-OK thing to say.”]

If you hate confrontation and really struggling with this, try to keep in mind that they might be—consciously or not—attempting to validate their own worldview or determine where your limit is, and will take anything less as a hard “wow, absolutely no” as a sign that their behavior is OK. If they’ve crossed the line, make that clear. 

Talking about the situation in terms of actual consequences makes it harder for them (though not impossible!) to downplay the situation or say it’s no big deal. For your part, that might sound like…

• “The way you kept badgering Lou when she clearly didn’t think you were being funny and wanted you to stop was really shitty, and, frankly, put a huge damper on what should have been a fun weekend.” 
• “I don’t know if you realize it or not, but you are getting a reputation as someone who doesn’t respect women—and, honestly, given [things they have been doing], I can see why that is.” 
• “I have to be honest, [behavior] is making me not want to hang out with you as much.”
• “I’m at the point where I worry about introducing my other friends to you, and I’ve started to wonder if I should warn them in advance about you, which is not a position I want to be in with a friend. I really need you to hear me and to cut it the fuck out.”

I also think it’s worth naming the bad behavior in really specific terms instead of relying on euphemisms to communicate what you’re upset about. There’s a huge difference between being circumspect and saying “what you did the other night” and saying “when you groped Harper’s ass the other night.” Your tiptoeing around the unsettling reality of what is happening doesn’t help anyone but the person causing harm. 

If the situation has reached a point where you worry that they are going to embarrass you in some way or feel the need to warn people about them… that’s a problem! At the very least, you should do what you can to stop subjecting yourself and your other friends to their behavior, or letting them use their proximity to you as a sign that they must be an OK dude. 

This is a great time to familiarize yourself with the Geek Social Fallacies (which identifies common friend group myths like “ostracizing anyone ever is evil” and “criticizing a friend under any circumstances is a betrayal”) and the Missing Stair (a really helpful framework for thinking about the lengths we often go to to avoid dealing with bad behavior). I learned about both of these from the wonderful Captain Awkward, who has a lot of great advice on the topic of creepy behavior in all sorts of very specific scenarios, starting with this post, which I highly recommend reading! 

Whether or not you tell them they are no longer invited depends on the circumstances—if it’s a standing or more formal invite, if they are asking directly to be invited or for your friend’s phone number, etc.—and sometimes it makes sense to simply pull away. But if you know in your heart you need to say something, or if they ask you directly about the situation, be kind but still honest. That might sound like…

• “The truth is, the way you talk about [women/sex/dating] makes me really uncomfortable and I didn’t want to have to deal with that [this weekend/at book club/anymore].”
• “If I can be honest, the way you’ve talked about [women/sex/dating] makes me really wary of setting you up with anyone, let alone a close friend of mine.” 
• “Hey—I think it might be best if you don’t join in the game night this weekend as planned. The past few times, you’ve [things they did] and it wasn’t fun for a lot of folks, myself included. I hope we can eventually get back to a place where I can trust you more, and where everyone feels more comfortable having you around, but I think that’s going to take some time.” 

None of this stuff is particularly fun or easy. Confronting people, criticizing their behavior, kicking them out of your group chat… it’s difficult and painful for everyone involved! But try not to let your fear of awkwardness or discomfort get in the way of saying what you know, deep down, needs to be said. If you actually care about someone, you should care enough to not let them run roughshod all over society. A true friend tells someone—thoughtfully, without malice, from a place of love and good faith!—when they are acting like an absolute asshole.