10 Difficult Personality Types—and How to Deal With Them

Got a complainer in your life? Or a contrarian, who always disagrees just for the sake of it? How about a chatterbox who just won't stop talking? Here's how to handle it.

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Difficult People One - Two people talking
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How to Deal With Difficult People

While politely making small talk at a baby shower, my day was ruined in one fell swoop. “Ooh, are you expecting?!” asked a family friend, eyeballing me up and down. I sheepishly shook my head, instantly regretting both my party dress and my plate full of mini-sandwiches. Then, just when I thought the conversation couldn’t get worse, it did: “Well,” she asked earnestly, “why not?”

My mind flooded with reasons and retorts—“just fat, thanks,” deep-rooted doubts about my maternal capabilities, fear of climate change, or perhaps a well-deserved expletive—but, sadly, none materialized. Instead I murmured a few words about being busy with work and excused myself to mope for the rest of the afternoon.

I’ve since recovered emotionally, but I sometimes daydream about a do-over. What should I have said to a nosy question from a rude person? And how about all those other, um, challenging personalities we have to talk to whether we want to or not?

I asked experts about how to deal with the trickiest, tackiest, meanest and most maddening personalities—with nary a single swear word.

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Difficult People - Woman complaining at restaurant
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The Complainer

You know the type: This restaurant’s too pricey, the music’s too loud, their burger is overdone and they can hardly taste it anyhow because they’re coming down with something. As Saturday Night Live’s famous Debbie Downer sketch goes: “Wha, whaaa, whaaaaa.”

In real life, the Complainer isn’t so funny. “This is a person who thinks life’s unfair to them,” says Jody Carrington, a psychologist and author of Feeling Seen: Reconnecting in a Disconnected World whose practice is in Olds, Alberta. Nobody is that bummed out by a burger; they’re down about other, bigger things and are taking it out on specific, controllable things like what’s on their plate (not to mention the unfortunate server who delivered it).

How should you deal with this good-mood thief? “If you want to interact better with these people, it starts with empathy,” says Carrington. (This is true for all tricky personalities, but especially for a Complainer.) Start by removing the small stuff from the equation—maybe let them choose the restaurant—so you can both focus on the big picture. Get them to talk about what’s really bothering them and challenge their negativity with questions about what’s good, fun and exciting in their lives.

Like the old adage goes, says Carrington: “You’ve gotta kill ’em with kindness and hope it rubs off.”

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Difficult People - One thumb up and one thumb down
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The Contrarian

You say it’s a nice day; they say it’s too hot. You’ve read a good book; it was the worst book they’ve read in a decade. You mention that they contradict everything you say; they say, “No, I don’t!”

“A Contrarian is someone who just likes to argue,” explains Mónica Guzmán, Seattle, Washington-based author of I Never Thought of It That Way: How to Have Fearlessly Curious Conversations in Dangerously Divided Times. “Sometimes this is fun, but other times it’s aggressive and unpleasant. The Contrarian can’t always tell the difference.” So while you’re arguing the issue at hand, they’re arguing for the sake of argument—and so they win every time.

How to better brave this battle? A Contrarian only wants to spar, so pick your battles. For anything inconsequential, says Ian Leslie, a London, England-based argument expert and author of Conflicted: Why Arguments Are Tearing Us Apart and How They Can Bring Us Together, “the most disarming way to handle a contrarian is to say you agree with them.”

This doesn’t mean you should lie; try “I agree with you on that” about something small and specific, or I can definitely see your point” if you truly don’t agree on a single thing. Then change the topic.

When you want to instead stand your ground, you can move the Contrarian beyond their default defence position by becoming a more nuanced opponent. “You can sometimes get them off the opinion showdown by asking them for their story or experience with a matter,” says Guzmán. Asking “How did you come to believe that?” or “Has that ever happened to you?” can move a conversation away from a competition of opinions and toward a personal perspective. You might learn that you value their opinion after all.

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Difficult People - Hands writing bla bla bla in notebook
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The Chatterbox

If you can’t ever seem to finish a story or sentence, chances are you’re face-to-face with a Chatterbox. Despite the cute name, they can be a frustrating bunch, explains communication expert Sandy Gerber of Vancouver Island. The author of Emotional Magnetism: How to Communicate to Ignite Connection in Your Relationships puts it plainly: “The Chatterbox is a story stealer. They identify with whatever you’re saying and then barf out a story about themselves.”

It can feel like the Chatterbox is constantly trying to one-up you, but it’s not necessarily true. They could be socially anxious, uncomfortable with silence or just extra passionate and excitable. But whatever the reason, they probably don’t even notice they do this, nor the deeper reason why.

“Particularly in kids, Chatterboxes could just as easily be called connection seekers,” says Carrington. “That’s all they’re after, but they’re not giving you the chance to connect back, so they talk even more.” And because they’re chatting a mile a minute in this tediously talkative Catch- 22, you might not notice until you’re irked on the drive home, having realized all your stories were hijacked.

Next time, try the phrase you’d least expect: “Tell me more.” Says Carrington: “Choose a topic and let them exhaust it. Ask them questions, follow up and really listen.”

Once the Chatterbox has run out of things to say, their need to be heard has been met, so now it’s your turn. Jump in with something like “I love your stories and I have one for you, too.” For once, the floor is yours.

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Difficult People - Person looking at phone
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The Tech Addict

Socially, few things are more annoying than someone repeatedly checking their phone in the middle of your conversation with them. Soon enough, you’re projecting sulky thoughts their way like, I’m boring you/You’re more concerned with whoever’s on that phone than me/You don’t care about me, explains Carrington. None of that’s necessarily true, but this is: “If someone is engaged in a great conversation, they wouldn’t care about their phone,” she says. Ouch.

Whether you say something or not, remember the Tech Addict’s annoying habits aren’t about you. “It’s rude, for sure, but sometimes we mistake the behaviour for more than what it is,” says Leslie. “It’s very possible they’re just nervous or anxious,” he says. It’s also possible their partner is stranded with a flat tire or their kid is sick. The point is, you don’t know.

So before you hastily rage at the Tech Addict’s blatant rudeness, focus instead on building a better conversation than whatever’s going down on Instagram.

You might never be able to achieve this, given the power of today’s clickbait, so if you’re close enough to a person, Carrington advises you to cheekily ask them: “What’s on that thing that’s so alluring?” Chances are they’ll apologize and sheepishly tuck the phone away. (But if the answer is something real, talk about it.)

Better yet, avoid the situation in advance by saying something like, “I’m really interested in catching up properly, so how about we leave our phones in the car?” If they indeed have that flat tire or sick kid, you won’t have to assume it’s because your stories all suck.

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Difficult People - Two people having a disagreement
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The Political Antagonist

Oh boy. This person’s ideology is fundamentally different than yours. They’ve read the news (and/or the dark web) and, as usual, they’re ready and eager to rumble.

No family is immune to political differences, though Guzmán has a particularly complicated case: She’s the liberal daughter of Mexican immigrants who voted for Donald Trump twice, and naturally they want to discuss differing politics loudly over dessert.

Like the Contrarian, the Political Antagonist loves to argue, only they’ve got a great big end game of changing your mind. They can’t, and won’t, change theirs, and neither will you, because you’re both passionate about your politics—which is exactly why they’ve singled you out for a fight. Sigh.

Turn that bad thought good, however, by remembering they chose you because they consider you a worthy intellectual opponent and cannot operate without you. “If they’re your adversary, you’re probably theirs, too,” Guzmán says.

Politics and religion used to be hard no-go zones of polite conversation, but not so anymore—and that’s a good thing. “Heat in a conversation is good,” says Guzmán. “It means you’re exposing yourself to different points of view and you’re learning and challenging each other.”

Ian Leslie concurs: “Many couples and families thrive on these discussions, which can sound like arguments. It’s all about having richer and more productive arguments, not avoiding arguments.”

How can you avoid a pointless squabble? “The line is personal hostility, and don’t cross it,” says Leslie. If you’re even nearing that boundary, turn down the dial. If your sparring partner is getting angry or aggressive, try Guzmán’s suggestion to de-escalate: “I’m sorry, I didn’t realize that this mattered so much to you.” You could continue with “tell me more,” if and only if a more productive conversation feels possible.

But if the discussion is just too heated, a distraction makes for an excellent exit strategy. Try “Time for pie! Apple or pumpkin?” (Because we can all agree on pie.)

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Difficult People - Woman cringing and covering face
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The Inappropriate Jokester

Every family has one, so let’s call him “Uncle Bob”: He’s loud and brash, his opinions haven’t changed since the ’80s, and just as you’re happily passing the potatoes, he decides to drop a totally inappropriate word or joke.

There are some possible explanations for the Inappropriate Jokester’s regular faux pas. “They could be blind to their prejudices, are trying to be controversial or are intolerant of other points of view,” explains Chuck Wisner, a Massachusetts-based leadership adviser, personal coach and author of The Art of Conscious Conversations: Transforming How We Talk, Listen, and Interact. But none of these explanations justifies discrimination.

Now, ah, this is awkward. Should you feign a chuckle to keep the peace or make a scene and confront Bob for his (racist, sexist, classist, homophobic) “joke”? Naturally, it depends. “If a person who represents that particular group is present, you probably need to intervene because it’s the right thing to do,” says Guzmán. You should say something both for that person’s dignity and to avoid your eternal guilt as silent bystander—an act that often hurts the offended person as much as the joke does.

But you don’t have to declare Uncle Bob a despicable racist and insist he change his ways this instant (he won’t). “Saying ‘Uncle Bob, that’s not okay,’” as Guzmán suggests, says everything that everyone’s thinking in few words. Or try Wisner’s phrasing: “That sounds racist to me. I know you don’t mean that.” The jokester is unlikely to double down with “I do, actually, as I’m very racist.”

If the comment is so inflammatory it sparks further conversation, be careful to critique the joke, not the person, and frame your criticism as your own. Wisner suggests saying: “To me, that joke is offensive. Let me tell you why.” This could be a good chat for later, when Bob is calm and alone, when there’s time for a non-confrontational conversation about what’s really going on.

“There’s something in every bad joke that says, ‘I’m frustrated but I can’t say it,’” says Guzmán. If you can get Bob to let it out, hopefully he’ll do better at the next family gathering.

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Difficult People - Man covering face with shocked expression
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The Drama Queen

“The Chatterbox on steroids,” in Carrington’s words, the Drama Queen (or King) is someone who similarly dominates the conversation, chatting your ear off about all the wild things you will never believe are happening in the “Worst. Week. Ever!” (The boring details of your week, meanwhile, can’t possibly compare so don’t even try.)

Ugh, why are they like this? “This person’s always exaggerating because they want to be the centre of attention,” says Gerber. The more they do this, the more we pull away from the over-the-top emotions of a life in constant crisis.

“We tend to avoid them because keeping up with the drama is an energy sucker,” says Carrington. “But this only means they’ll turn it up. They’ve often exhausted the people in their lives and are therefore coming on even stronger.” The Drama Queen desperately wants your attention and she’s also terrified she’ll lose it, hence the show she’s putting on in hopes you’ll never look away.

You might think the Drama Queen expects the royal treatment, but deep down what she wants to know is that you’d meet her for lunch without the dramatic display. Resist the urge to cut her off and instead set some boundaries you can both stick to.

“Be really clear in advance about what you’re willing and not willing to do,” says Carrington. Maybe this means you’ll talk about her ex for 20 minutes but no longer. Or maybe it means you reschedule lunch until “a week when you’re feeling better.” She might be mad in the moment, but the Drama Queen secretly loves the regular-person treatment that shows you’re sticking around for the real her—no drama required.

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Difficult People - Woman turning away from another woman
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The Frenemy

Though all these personalities are difficult, perhaps none is more so than the Frenemy—that is, someone who is equal parts friend and enemy—a phenomenon so subtle, personal and complicated that sometimes you have to be in it to know it’s there. “I call this a see-saw friendship,” says Gerber, “because of the highs and lows—you never know what you’re going to get.” One day your friend is fun and fab and a blast to be with, while the next they’re low-key mad or mean—and you have no clue why.

Except really you know exactly why: “The Frenemy is a passive-aggressive person motivated by their perceived lack of value,” says Gerber. “And they’re rolling their eyes at anything that you have or do that feels like it’s undervaluing them.” To feel better about themselves, the Frenemy is desperate to knock you down a little bit at a time.

When dealing with a Frenemy, protect yourself by recognizing a negative judgment and not taking it personally. “These people are almost firing arrows at you,” explains Wisner, “so you can dodge the arrow, let the arrow pierce and hurt or offend you, or you can catch the arrow and stop it.” Options A and B are easy in the moment, but C is the brave choice if you want things to change. To start a difficult conversation, Wisner suggests saying, “That doesn’t feel sincere to me. Did you mean that?”

That might address a particular jab, but if you actually want to fix and save the friendship—and maybe you don’t—you’re going to need to dig deeper. “These people are highly competitive on the surface, but underneath they’re insecure, hurt and highly distrustful,” says Gerber. To turn a frenemy into a real friend, you’re going to have to open up and talk about it. “Tell them what you’re looking for in a friendship and what you’re willing to offer,” she says. “But if they can’t or won’t have that conversation, well, that’s your answer.”

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Difficult People - Woman covering mouth
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The Oversharer

Unsolicited commentary about someone’s sex life, their best friend’s messy divorce or whatever just happened in the bathroom (yuck) are all clues you’ve got an Oversharer on your hands. Whether they’re telling too much or asking for details you’re not comfortable sharing, this all-too-common persona has neither a filter nor boundaries.

Why oh why would anyone in their right mind list their irritable bowel syndrome symptoms over brunch? Because they have two specific human qualities overlapping at once. The first is an unwritten personal boundary that’s far, far from yours.

“The discomfort you feel comes from a difference of standards about what topics of conversation are okay,” says Wisner. “What they consider to be acceptable, need-to-know information is different than what it is for you.”

At the same awkward time, the Oversharer is only trying to get closer to you by revealing more about themselves—and hoping you’ll be similarly forthcoming. “We tend to label these people as nosy, invasive or rude,” notes Gerber, “but they really just want to be liked and accepted.”

To satisfy the Oversharer, and simultaneously veto the endless commentary, consider sharing something else—still personal but less invasive, ideally that satisfies their urge to connect. When they really cross the line, don’t be shy (they’re not), and say something that indicates your boundary is being crossed. “Omg, that’s private!” says everything, and you’ll never have to bring it up again.

A compliment also works wonders with an Oversharer, adds Gerber, because it refocuses the conversation in their direction while subtly resetting your boundary. For example, I could have given this wise response to my nosy family friend who asked about the state of my uterus: “You made having kids look so easy! How did you do it?” (Then nod and smile, nod and smile.)

I won’t get my baby shower do-over in this life, but next time I’ll be ready to face an Oversharer—or any of the challenging people it takes to make a world.

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Reader's Digest Canada
Originally Published in Reader's Digest Canada

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