This is *exactly* what to say during the most awkward conversations


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Awkward conversations can be funny—if you’re observing them while binge-watching episodes of The Office. But if you’re actually a party to one? Insert Jim-deadpanning-the-camera face here.

Whether you’re confronting a noisy neighbor or dumping someone who doesn’t see it coming, there’s one thing that can make uncomfortable discussions a little less painful: some advance prep work.

I tapped a few therapists—you know, the people who have difficult conversations for a living—for tips on what to say and avoid during exchanges that need to be handled with care. Their tips will ensure the person you’re talking to feels respected and supported, while giving you the space to speak your truth when it’s appropriate. (And no, it’s not always appropriate, as you’ll soon learn.)

Here are the scripts you need to navigate 5 truly unpleasant conversations.

How to have awkward conversations
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The “Your partner is cheating on you” talk

You’re out to brunch and you spot your friend’s S.O. canoodling hardcore… with someone who is most definitely not your friend. While your first instinct may be to pour your matcha in the offending party’s lap, hang tight and think about your pal first.

There’s no “one-size-fits-all” way to deal with this situation, says Laurie Sloane, LCSW. For instance, if the friend in question is only someone you know casually, it may not be your place to step in. But if you’re basically besties, you may feel obligated to bring it to their attention. “You need to think long and hard about how they will feel,” Sloane says. “Knowing what you know about them as a person, you have to take into consideration how they might react. Would they want to know?”

While you may think you know your friend very well, you might not know everything about the level of monogamy they may have with their partner, says Alice Shepard, PhD. Rather than spill what you know outright, just ask how things are going with their relationship.

If you come to the conclusion that your friend is in the dark—and you think this is something they’d want to know—Sloane suggests leading with a reminder of how much you love and care for them, and bring up a time when they helped you get through a difficult time. “Tell them you thought at great length about telling them and [about] how this might affect them,” she says. “Tell them ‘I love you and I’ll support whatever decision you make. However I can help you through this, I will be there.'”

While there’s always the potential of a shoot-the-messenger scenario, just remember to frame the conversation around your love and respect—and resist all temptation to be judgy, no matter what your friend decides to do next.

How to have awkward conversations
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The “I’m just not that into you” talk

In a perfect world, every first date would lead to a dreamy haze of stargazing adventures, all-night conversations, and mind-blowing sex. Unfortunately, life doesn’t always work that way. If you’re feeling lukewarm about the one who’s blowing up your texts, it’s time to end things with that perfectly okay person.

First rule: Don’t ghost, even though you may really want to.  “That’s the most hurtful thing a person can do in this situation,” Shepard says.

If this was a very casual relationship—say, a few coffee meet-ups or flirty app messages—Shepard says a kind email or text is okay. But if it’s been a more intimate courtship, involving romantic dinner dates, long talks, or R-rated booty calls, you should really break things off face-to-face. “It requires more humanizing,” says Shepard. 

Translation: Don’t mince words, but don’t be cruel. Say you truly enjoyed your time together, but it’s simply not the right fit. Yeah, it might suck. But it’s better than going down a path that will inevitably lead to disappointment for everyone involved.

How to have awkward conversations
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The “Can I borrow some money?” talk

Let’s say you have a great idea for a wellness business and you want to get the wheels in motion. Or you need a down payment for your dream apartment, but your bank account just isn’t showing you the money. You may consider requesting a loan from the Bank of the ‘Rents—but just because family’s involved, that doesn’t make the ask any easier.

“The whole issue of money is very charged,” Sloane says. Before you approach a family member with a financial proposition, she suggests you consider how the emotional factor of borrowing money will affect you, as well as how much your loved one really has to contribute.  Even if your relationship is strong, Shepard adds, try not to make assumptions about their finances. “Let them know whatever they decide—whether they can give you all of it, or half, or nothing—it’s not going to affect your feelings about them or your relationship,” she says.

Shepard also points out that a big decision like this isn’t likely to be finalized in just one conversation. “You really want to have the emotional conversation first, and then work out the details,” she says. And be transparent, says Sloane. “You need to lay it all on the table: Why are you asking them? What are your your plans with the money? What’s the anticipated repayment trajectory?” She suggests putting the plan in writing and possibly involving a lawyer “to get into the nitty gritty.”

How to have awkward conversations
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The “Will you please keep it down?” talk

When you live super close to your neighbor—like, on the other side of a thin apartment wall—you’re bound to hear some things. But what if your morning meditations are being interrupted by every play of the new Drake album, every fight with the partner, and every subsequent round of make-up sex? It may be time to say something.

Shepard suggests assessing the situation so that you have an overall sense of the neighbor and how receptive they may be to your requests. Your best bet is to start by leaving a note, she says. “Have the note read, in the nicest way possible, that the building doesn’t exactly have adequate soundproofing,” Shepard suggests.

And if the note doesn’t do the trick—or you feel you have a good enough rapport to chat face-to-face—Sloane says to be straightforward and respectful. “Tell them, ‘I know you’re not aware, but I’m hearing private things going on in your apartment. I know it’s awkward to think I’m hearing every detail, but I am, and I want you to be able to maintain your privacy.'” Because, let’s be real—they probably don’t want you to be listening in on their most intimate moments, either.

How to have awkward conversations
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The “Care for a mint?” talk

We’ve all fallen victim to bad breath at some point. (Even Meghan Markle’s not immune—there’s a reason why the royal family’s banned from eating garlic when they’re on official trips.) But what if it’s happening on the reg to your cubicle-mate at the office, and she seems completely oblivious?

Like so many of these scenarios, this one is hugely dependent on your relationship with your coworker. If it’s the payroll guy you hardly ever talk to, stay far away from bringing this one up. Same goes if the person reports to you—this could create a power dynamic issue, our experts say.

But if you consider the colleague a close friend and you have a lateral work title, bring it up—but tread very lightly. Sloane says you can subtly offer mints or drop hints about your new wasabi-flavored toothpaste. But if that doesn’t do the trick, have a heart-to-heart in which you tell them you just want the best for them. “You can also ask them if they are feeling well,” she says. “Really terrible breath isn’t always an issue of hygiene, it could be an indicator of a health problem.”

And if you still don’t feel comfortable bringing it up, Shepard suggests checking in with HR, who may agree to do the dirty work for you. After all, Sloane adds, “You wouldn’t want a friend to suffer the consequences.”

Another awkward conversation: Breaking up with your roommate. If things go south, here’s how to know whether or not you can salvage the friendship.

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