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What to Do When Your Best Friend Gets Back With the Ex You Hate

Male psychologists, communication experts and etiquette legends help you sort out the tricky politics of speaking up

Oh, no — don’t look now. It seems your good friend “Matt” is getting back together with his ex, “Mandy.” (Or Micheal, whatever. Sub in anyone you like.) 

This is not good. Cupid kind of missed the mark with that pairing. Their relationship was always a little more Britney and Kevin than Romeo and Juliet, so you’re a little surprised either of them is gearing up for round two. Why sample the same gas station sushi after it made you shit your brains out the first time? 

Plus, you’re pretty sure this whole Return of Mandy business isn’t going to bode well for your friendship. He’s different when she’s around. He pretends like he doesn’t want to play naked Jenga with you, and sometimes, you don’t see him for weeks or months at a time (except when he crashes on your couch after another fight). And when you do see him, he seems exhausted. Or angry. Or sad. Then you get sad for him! Ahh! 

You’re worried about Matt and think he deserves better, but you’re also not sure what to do. Should you speak up and let him know you think this is a bad idea, or should you cool it and let it slide?

Wait, don’t answer that. Let me answer for you. Because I’ve gone and assembled a transcontinental team of male psychologists, communication experts and etiquette legends to help you sort out the tricky politics of this very issue, and they’ve come up with a game plan to help you every step of the way. 

But first, let’s try to understand what’s really going on here. 

Why Is He Doing This?

Only he can say for sure, but according to Peter Gill, a psychologist who studies male friendships at the University of Victoria in Melbourne, it might have something to do with the dark, demented truth that for some people, staying in bad relationships keeps them from having to confront themselves (oh yeah, we’re going there).

“Difficult relationships tend to occupy a lot of one’s thoughts,” he explains. “They also stir up a lot of negative emotions and drama, both of which tend to distract you from having to deal with the underlying causes of your problems.” Without a bad relationship to use as a scapegoat, these problems might bubble to the surface without explanation, which Gill says can be “frightening” for some men. By contrast, when they’re caught up in a bad romance, it’s easy to blame all their shortcomings and misfirings on it. So, though Matt probably knows getting back together with Mandy is iffy, he might also sense that it’ll keep him from having to be alone with himself. After all, when they’re together, she is the problem, not him. 

Another, less believable reason: Maybe he just really likes her. Even though he’s probably wasted three or four prime years of your life complaining about her to you, there are probably some parts of her that he finds intoxicating (even if you can’t possibly imagine what they might be). Maybe she’s controlling, but he’s looking for a mommy-figure. Maybe she cheats on him, but he’s secretly a bit of a cuckold. Maybe she isolates him from you, but he actually wants to spend time with a new group of friends.

“The heart wants what it wants,” says Geoffery Greif, author of Buddy System: Understanding Male Friendships. “It’s his life not yours, and you have to remember that you’ve only gotten a filtered version of their relationship from your friend.” 

So could it be possible that she’s not as bad as you think? 

No. She’s Terrible. 

Okay, then, it would make sense why you feel weird about this. 

Why Do I Feel Weird?

According to what Gill knows about male psychology and communication, it’s probably because you can sense that your friendship is about to change. If you and his ex don’t get along, or you’re demonstrably suspicious of her, you and your friend will probably start hanging out less. He’ll stop confiding in you, and you have to watch an important relationship turn from a beautiful, scrumptious summer grape into a shriveled raisin that gets picked out of the trail mix. That would make anyone feel weird. 

Likewise, you also know from being his friend that their relationship kinda sucked the first time around. You might be empathizing with the tornado of pain he’s about to wreak on himself by getting back together with her, and that might cause you to feel emotions like sadness, anger, wariness, exhaustion or apathy. 

All of which is completely normal. If you care about a friend, seeing him getting back with someone who is a bad influence can be upsetting,” says Greif. “This is especially true if you supported him in separating from her in the first place.” 

Should I Say Something Then? (I Definitely Want to Say Something.) 

That depends on the kind of outcome you’re going for. According to Greif’s research, most men like when their friends “tell it like it is,” but there’s also something to be said for a friend who listens and tries to empathize before they step in with their opinion. Which route you take depends on the specifics of your friendship and the situation with his ex, but Gill’s baseline advice is to only speak up if it would help maintain your bond as buds. In other words, if your friendship is being harmed by Matt and Mandy’s perplexing reunion, you should say something. 

“Mateship [Australian for ‘friendship’] is so important to men’s health that every effort should be made to preserve it,” he says, explaining that it can be just as detrimental to you to hold in your feelings about this as it can to let them loose. “Men are often really bad at communicating to their partners just how important their mates are, which can result in the neglect of their friendships and drifting apart, so I encourage men to reach out to their mates about issues like this in order to keep them close. This could be achieved through actions/gestures, direct communication or indirect jovial ways, so long as the message gets across.” 

I’m Gonna Need Some More Specific Direction Here.

How about some advice from Daniel Post Senning, the co-host of the Emily Post Institute’s Awesome Etiquette podcast?

I’m Listening… 

Cool. So before you talk to your friend, Senning recommends you prepare by doing three key things. 

  1. Make sure you have enough of a rapport with him to have this conversation in the first place. If you’re just the guy at the gym he winks at when he’s sculpting his tri-delts, your opinion is probably meaningless to him. If you’re his childhood best friend and you know the ins and outs of his relationship, it’ll carry more weight.
  2. Understand the value of listening. Your opinion is important, but so is your friend’s. That’s why Senning recommends that you only talk to him about this if you’re willing to hear what he has to say. “Prepare yourself to give equal time to him to tell you how he feels and how he’s doing with all this, knowing he might have a very different opinion about it than you do,” he says.
  3. Prime him for having a potentially difficult conversation with you. Ask him if he has the time to talk with you or see when he might be free to chat. Then, let him know there’s something a little, er, awkward you’ve been wanting to talk to him about. “Priming is a psychological tactic,” explains Senning. “You’re essentially giving him permission to not have the conversation, but if he takes the bait, you know he’s at least somewhat ready to listen to what you have to say.” 

An addendum: Make sure you have a good reason to talk to your friend about this in the first place. We’re talking about a relationship with a person he clearly — though inexplicably — cares about, so you need more to work with than “We don’t spend time together when you’re with her,” or “I saw her talking to another dude at a bar.” 

Think she’s kind of boring and forgettable? That’s not gonna fly. Disagree with her ideological or political leanings? Cute, but that’s not gonna work either. You need something compelling. Something that affects not just you, but your friend and his well-being. 

Like What? 

Well, think about why your friend and his ex are exes to begin with. What happened between them that caused them to break up? Is that thing is still a factor?

For example, was there an unforgivable cheating incident? Is he in recovery and she’s his dealer? Does she socially isolate him so he loses connection with his friends and family? Are they terrible at communicating with each other, but haven’t done anything to rectify that? Does she manipulate him financially or depend on him for money? Is she insistent they have a relationship or family structure he doesn’t want? Does she refuse to go to therapy? I could go on. 

If none of these things (or anything like them) fit the bill, Gill recommends you keep out of it. 

Don’t Worry, I’ve Got a Good Reason. What About the Actual Conversation, Though? 

What a prize-winning segue. Here comes another list, courtesy of Senning: 

  1. Be explicit about your intentions. Let him know you’re bringing this up because you care about him, and that you hope he’d do the same if the shoe were on the other foot. Make it clear that you want to see him happy so he knows this is coming from a good place. And then? 
  2. Let ‘er rip. Say what you need to say to him, taking care to be clear and direct, but also to give him space to respond. “When conversations are difficult or potentially awkward, it’s really worth it to be honest and candid about what your issues are,” says Senning. “That way, there are no misunderstandings, and you come across like you’ve thought everything through.” 

Basically, it’s okay to go straight for the kill with something like, “Look, I know you care about Mandy, but it seems like you’re really unhappy when you’re with her. You also hang out with your friends a lot less, which is cool, but I just want to make sure you’re okay going back to that, because it seemed like it was really hard for you the first time around.”

Gill also recommends you focus less on what you want and more on what your friend wants and where he sees himself in the future (this is a conversation about him and his relationship, after all). One big caveat, though: “I’d do this with the knowledge that it may have no effect,” he says. “Your friend may ‘need’ the drama that this bad relationship brings, so the overall focus should be making sure your friendship stays strong.” 

Oh, and try not to bad-mouth dear Mandy during this conversation either. That’ll just make you look bad. Keep the conversation limited to what you’re concerned about, trying to understand where your friend is coming from and offering your support if he needs it. 

I Don’t Think You Understand. Mandy Is Insane. What If She’s Abusive or He’s in Danger? 

Shit, why didn’t you say something? If Mandy is actually abusive or she puts your friend’s mental or physical health in danger, throw everything you just read out the window and step in with a much more direct conversation that cuts to the chase immediately. Don’t worry about priming him or thoughtfully explaining that you’d want him to do the same for you if the tables were turned. Time is of the essence in a situation like that, so let him know exactly what you’re noticing and why you’re concerned. “When someone’s physical or mental health is in danger, safety always trumps etiquette,” says Senning. “By all means, jump in and confront the problem.” 

At the same time, know that it’s not your job to save your friend from his relationship, nor can you coax or force him to leave it. Instead, the best thing you can do — aside from offering him practical help and resources — is to let him know you’ll always be there for him and that he can always come to you for support, which, let’s be honest, he’s probably going to need. A simple “Your relationship is your business, I’m always here if you need me,” should suffice. 

Wait, Actually, She’s… Fine. It’s Just That He’s Different Around Her. I Miss Him!

Yeah, you’re fucked. Sorry, dude. 

Just because he’s changed his habits or personality now that him and Mandy are back together doesn’t mean they’re wrong for each other. They might feed each other in some strange way you’ll never understand, or the way he’s changing might actually be good for him. Who knows — maybe spending less time with you and your other friends is helping him benefit from the types of validation only a romantic relationship can give. 

It can be jarring when your friendship changes like that — especially when it seems like someone else is to blame — but that’s life. Relationships grow and evolve, and they rarely look like they did when they first formed. The best thing you can do is grow and evolve with them, knowing that sometimes, you have to let people go if you want them to come back to you. 

Are you crying on or embroidering a Live Laugh Love pillowcase? Because I am. 

Yeah, I Am Too. Friendship, Like Love, Is Bittersweet, Like the Final Kiss of a Dove Before It Flies Into the Sunset. So Does That Mean I Have to Play Nice With the Ex?

Kind of, yeah! 

Assuming she’s just a garden-variety offender and not Ted Bundy, Senning says you’re pretty much required to show her basic respect and courtesy whether she’s with your friend or not. Talking shit about her behind her back, undermining her plans with your friend, snipping at her, rudely ignoring her or trying to sabotage her is “absolutely inappropriate.” That doesn’t mean you have to kiss the ground she walks on, but it does mean that you have to treat her like you’d want to be treated. 

That Sounds Excruciating. 

It probably will be, which is why Greif recommends you try to spend as much time with your friend without his ex around as you can. 

What If She’s Always Around?

Then do your best impersonation of someone who focuses on their own problems and do your best to see things from your friend’s point of view. 

“Relationships have their own secret language, and the people who are participating in those relationships reach agreements and understandings that would seem inscrutable or indecipherable to the outside world,” says Senning. “You’ve got to remind yourself that as an observer and not a participant, you’re probably not speaking the secret language of that relationship as well as your friend.” 

So, act cool, be nice, smile and nod, and make sure you have a really great conversational out if and when she tries to talk to you. 

Should I Like, Subtly Let Her Know I Disapprove?

Nah. Focus on your friend. If you make little innuendos at her or say something to her about it, it’ll likely get back to your friend, and you’ll look like the weirdo for not addressing the situation with him. 

What If None of This Works And My Friend Hates Me Now?

You next him and his little ex, too. “You might have to kiss the friendship goodbye if he doesn’t like what you said and knows the three of you can’t spend time together,” says Greif. After all, if it’s more pain than it’s worth, that’s a sure sign that you should let it go and move on to the next romantically confused male friend. I’m sure he’d be no Matt, but again, that’s life.