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The Gentleman’s Guide to Confronting the Fuck-Up in Your Friend Group

It may not always be easy for a guy to have a heart-to-heart with another guy, but sometimes it has to be done

Ah, the fuck up in your friend group. You know the one: The one guy who manages to be notably more of a fuck up than the rest of you. Perhaps he can’t keep a job, or still lives with his parents in the exact same room as he did when he was in high school, the same old posters of Rebecca Romijn on his wall. Maybe his brand of dickish hilarity no longer holds up in our #woke world. Perhaps the problems are even more serious, like an addiction he’s done nothing about.

Whatever it is, it needs dealing with, and while it’s tough to have to “get real” with your guy friends, deep down, you know this one’s on you…

Psych Yourself Up

More than likely, the biggest hurdle you’re going to have to overcome in this process of confronting your friend is your own anxieties around it. You may be used to talking about sports, music, that new IPA at your local brewery or other superficial friendly banter, and to suddenly have to talk about real-life shit isn’t going to be easy. To deal with this, you’ll have to keep focused on your goal: Know that you’re doing this from a place of love and keep in mind that the goal of helping your friend is more important that your own discomfort.

Round Up a Posse

Obviously, things will be easier if you don’t go it alone, so talk to your other, non-fuck-up pals about helping you out. Substance abuse counselor Terrence Connor points to the effectiveness of an intervention versus a one-on-one confrontation, saying, “If you hear something once, you might not take it too seriously, but if you hear it from multiple people who care about you, it’s much harder to ignore.”

The same principles can be used for any kind of fuck up, as long as everyone who’s confronting that person is on the same page. You can’t have one guy chicken out halfway through and start defending the fuck up, and if it’s an addiction you’re talking about, one person can’t be an enabler while the rest are doling out tough love. It needs to be a unified front so that the message is clear.

Regardless of whether or not you can get your friends on board, the conversation must be had, so don’t use the excuse of them not helping as your reason not to do it.

Make a Plan

While it’s never good to be too over prepared, you probably want to have a basic idea of what you’re going to say beforehand. Psychologist Frank McAndrew says that the way to go about this is to, “Be apologetic and make it clear that this isn’t about you trying to push someone around.” Whether you’re doing this in a group or flying solo, you want to make it clear that you’re there for this person no matter what.

This kind of vulnerability can be especially hard for men: Psychologist and author of Buddy System: Understanding Male Friendships, Geoffrey Greif, explains that men are usually conditioned to compete against one another, and because of that, showing weakness is tough. But the commitment to your friendship and your friend’s wellbeing has to be a constant theme throughout. McAndrew adds that it’s important to, “Try to explain how his lifestyle is leading to unnecessary problems for the guy himself,” rather than just saying how it’s bothering others.

Pick a Spot

Where you’re going to have this conversation is going to depend on your audience and how many people are involved. For one-on-one conversations, certified life coach Lindsay Jackson says it’s probably best to “find a really masculine setting,” like after bowling or some other typical male bonding activity, so you avoid an awkward situation where you’re both chilling on the couch and suddenly you decide to get “deep.”

For the intervention type scenario, you’ll likely want to go with someone’s home, especially if you’re dealing with a problem as serious as addiction. In those intense conversations, you need to be able to let it all out.

Have the Heart-to-Heart

During the big talk, you want to be clear and you want to get your points across without too much emotion. McAndrew reiterates that you want to be sure to, “Frame this as concern for your friend’s well-being, rather than a rant, an ultimatum or petty complaining.” So tone is important, as is letting the fuck-up friend talk.

The person might get defensive by pointing out one of your flaws in return, but it’s important that you take it in stride and remember why you’re there. Jackson likes to use the expression, “Kick their butt while holding their hand,” so make your points direct, but also make sure that you express your compassion throughout.

“Think what you would want to hear and how you would want to hear it if the shoe was on the other foot,” advises Greif, explaining that by doing so, it’ll help you to remain empathetic throughout.

Know Your Fuck-Up Types

Obviously, every serious talk like this is going to have its own nuances, but for some of the most common fuck-up areas, here are some tips:

If Your Friend Is a Sexist Asshole. If you’re confronting a friend about inappropriate behavior, you may want to take a page from the HR world, where people often have to have hard conversations about inappropriate behavior. Human Resources Manager Vanessa Fils-Aimé says that you’ll want to come into the conversation with specific examples of the behavior, then you can proceed to explain why it’s wrong and how their actions or comments can make someone feel.

Obviously, the tone of your conversation will likely be much different than a work/HR talk. As we outlined in our piece about how to call out your guy friends on their sexist bullshit, keeping things light by joking about it can be effective, as long as you don’t back down if they tease or challenge you.

If He’s Got Money Problems. No one likes to talk about money, but, “People generally know if they’re in a bad situation,” says financial advisor Adam Ditsky. With that in mind, “Putting people down further is rarely effective,” says Ditsky. Also, beating around the bush justs wastes time, so you should be direct, but not so direct that it’s hurtful.

No matter what your friend’s financial woes are, Ditsky believes that it’s never wise to compare their situation to your own. Financial conversations also can be tough because you may not be able to help the person in any direct way: Loaning money to your friends can get ugly quick, and Ditsky says that the only way you can even consider it is if you’re okay with never seeing that money again. That said, simply having the conversation may still be what they need to finally confront their personal problems.

If He’s an Addict. Confronting an addict is the most difficult of any scenario you’re likely to encounter, so you’ll want to proceed carefully. Connor cautions, “The addict is very sensitive and doesn’t want anyone to get in the way of their addiction.” In this situation more than any other, having a group with you will be beneficial. You may even want to bring in some family or other important people to have an outright intervention.

Connor says that you and everyone there needs to utilize tough love: Let them know that you love them and that they’re special people to you, but that you’re not going to enable them in any way. Most importantly, though, Connor says to be patient. You may never know when an addict is ready to hear this, so you may be successful, or you may have to do this all over again in a few months.

If All Else Fails, Write It Down

If you can’t have that hard conversation in person, an alternative is to write a letter. In this case, you’ll want to refrain from texts or any other sort of casual format and write something thoughtful in a very careful way. The advantage of the letter is that you can be exact about what you want to say. Don, a former “fuck-up friend” of mine, recalls when a friend of his sent him a letter:

“Ever since we were 15, my best friend and I had always talked about going into business together, but when I turned 23, I moved out to Vegas. While I moved out for several reasons, one of them was to experience a life with very few consequences. That lifestyle became addicting, and when the recession hit, I was laid off and turned to playing poker full time, which wasn’t a sustainable living.

“It was shortly after this that my friend sent me a heartfelt letter that bluntly asked me what I was doing to contribute to this future that we had planned together since we were kids. For someone who always has something to say, I had nothing. I was embarrassed, but I never saw it as coming from a place of judgement. It was more of an observation, and I knew it came from a place of love and caring. Afterward, I started to open my eyes to other patterns of selfish behavior too.

“Shortly after that, I realized that there was no reason to be out there anymore, and I moved back to New York. Now my friend and I are still on that journey together, and I’ve never been happier.”

Be There

No matter the situation, or what kind of fuck up your fuck-up friend is, McAndrew assures, “If you have a solid relationship and have a history of being a good friend to each other, he will listen.” If you can say what needs saying and be compassionate throughout, you may actually break through and help them in a way that they really need. A friend in need is a friend indeed, as they say, and if your friend needs a swift kick in the pants, you’re the guy who’s going to have to deliver it.