I Would Rather Date the Devil than a Devil's Advocate

I’ve always said that I don’t have a type, but I do love people who are intelligent, open-minded, and great conversationalists. Unfortunately, a percentage of that population coincides with the camp of people who love to play devil’s advocate.

Honestly, I hate it when people play devil’s advocate. Maybe it’s because I’m fiercely loyal, or maybe it’s because I hate making people upset. For whatever reason it is, when a partner or a friend of mine tries to argue both sides of something in a conversation - and they passionately pick the side opposite of mine (for fun) I tell them that this is not fun and they should just agree with me instead or say nothing.

If you truly have the opposite viewpoint of me - please tell me about it! I would love to hear it, I love hearing different opinions and I’ve changed massive parts of my life due to conversations like that.

But if you agree with me from the start, and then decide to take the opposing side and argue that for ‘fun’? Well to me that just isn’t fun. There’s enough strife in the world, baby. We’re on the same side of something - let’s fucking enjoy it for a minute.

Some people might call this mindset immature. But I’m 25, so I get to be immature!!! (I’ve tried this excuse with boyfriends before - it doesn’t work.)

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Last month, Bridget came into town for New Year’s Eve. Ace insisted that JG Melon has the best burger in New York, so Bridget and I trekked the 20 minutes to the Upper East Side to meet him and TJ there for dinner.

Everyone at that restaurant was an asshole. The hostess wouldn’t seat us until everyone in our party was there (despite plenty of open tables). Our waitress rolled her eyes at my peanut allergy. Bridget didn’t order the hamburger and was shouted at by our server. They forgot to bring condiments we asked for, and when we asked for them in the first place, we were given huffs and nasty looks.

“This place sucks, why are they so rude here?” I asked.

“Oh, it’s amazing,” Ace grinned, wolfing down his cheeseburger. “That’s their thing, they’re rude here.”

“Seriously? Why?” Bridget asked. Ace shrugged.

“Well it’s mean, nobody likes being treated this way,” I said.

Ace, similar to the entirety of our waitstaff, rolled his eyes at me.

“I like it,” he insisted. “It’s part of the experience, it’s fantastic!”

“The waitress just yelled at Bridget for ordering an omelette!” I shouted. “She was rude”

“So?” Ace said. I could feel him getting irritated.

“So we’re your friends. We’ve known you for years, you’re having dinner with us. You’re really going to take the side of the waitress who you’ve known for 2 minutes and is being mean to us?”

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After a post-dinner drink at a nearby bar, and some calming down on my part, we had a great rest of the evening. Bridget and I headed back to my apartment, and Ace hopped in the car with us.

“Such a good meal,” he said from the front seat as we drove past the East River. “Man, they’re so rude there though, so rude. I don’t get it, why be so mean?

I rolled my eyes from the backseat. Of course he agreed with us in that restaurant. No one could argue against the fact - they were rude. Ace just loved to play Devil’s Advocate.


Most of the time, when someone plays Devil’s Advocate, I’ll indulge them. I’m a political moderate, I date both men and women, if anyone is able to see both sides of an issue - it’s your friendly local bisexual independent.

The thing that mainly steams me about people playing Devil’s Advocate, is when they do it for minor things.

I once dated a guy named Jack who did this constantly. We were living in Houston at the time, and driving to dinner on a crowded Friday night.

“This traffic is horrible,” I had remarked. We had been sitting in the same spot for 3 minutes.

“Actually, it’s not bad” he had said, “usually it’s worse at this time”

I paused.

“Do you like sitting in this traffic?” I asked him

“What? No.”

“Then can’t you just agree with me that it’s bad?”

"Did you know what I mean? Then don't be a dick about it."


I know that in these stories I come across as a critical bitch who nags on someone for a tiny thing they say. Because all of these things are tiny. They’re so tiny.

One man’s argument of “it’s fine to disagree on that because it’s so small,” is another man’s argument of “why bother disagreeing on that? It’s so small it’s not worth the disagreement” and I have to say I fall into the later camp.

If we’re talking about politics, or religion, or anything big, I love to have my mind challenged. Let’s take different stands, let’s explore how we think, and why that is!

But when someone plays Devil’s Advocate for something minuscule, like the traffic or whether or not a rude waiter is rude, it isn’t playing Devil’s Advocate for the sake of explorative conversation. It’s just being a dick.

(In my opinion).

Disagreeing with my viewpoint on something massive piques my curiosity. But disagreeing with my viewpoint on something universal (like how traffic is bad) just shows to me that you’re trying to be argumentative, and you don’t respect my opinion. You know that I don’t like traffic. I know that you don’t like traffic. When you start a Devil’s Advocation that traffic is good, it makes me feel like you’re fighting just to fight - because I know you don’t hold that viewpoint.

And honestly, it bums me out. When someone plays Devil’s Advocate it makes me feel like we’re not on the same team, and I think it can be horrible in a romantic relationship especially.

I think this also falls in the realm of being critical.

Devil’s Advocates, by nature, are critics. I’ve been performing improv comedy for about 6 years now, and the Number 1 Rule of improv is: Yes, and.

When someone starts a scene with you, you have to “yes, and” them. No matter what.

I’ve had scenes where I walk on stage, and a team member shouts, “There it is! The fattest giraffe you’ve ever seen!”

And I have to “yes, and” that shit. I have to stretch my neck, and start waddling on stage (the ‘yes’ part), and then sign up for a hot dog eating contest (the ‘and’ part). Can it be embarrassing? Who gives a fuck, it’s improv! But using “yes, and” does make for an incredible scene when you use it time and time again.

Critics don’t “yes, and”. They say no first. They find flaws before they find solutions. They offer advice before they offer support.

One of my favorite quotes about this comes from my former boss: Stephen Colbert. (Also, yes I’m an asshole, I only interned for his show one summer. He wasn’t my boss.)

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Cynicism, and playing the Devil’s Advocate is easy. My god, it’s so easy!

It’s very easy to tear down someone’s idea, to say “no”, to argue for the exact opposite view of what someone said, purely because it’s just the opposite. All of those things are easy, and simple, and they don’t take much effort.

It’s so much easier to break something than it is to build.

Saying “yes”, and putting yourself in someone’s shoes, and understanding their viewpoint is a hell of a lot harder. But I think that it’s better, in every aspect.

If Ace agreed with me about that waiter at JG Mellon, we would have all had a laugh about it. Maybe we would have dared someone in our group to ask her for a spoon to go with our burger. We would have given her a nickname, or asked her to take a photo of our group and see what the reaction was.

But by playing Devil’s Advocate, it was Ace and the Waitress vs. Us, which put a halt on the comradery and bonding of the night.

(Also - as a quick note, I love Ace to death. And I promise to write a blog post next where he shines!)

I’m not looking to live in a world where everyone agrees with me - and I hope it doesn’t come across that I’m thinking that way. But I want to live in a world where people are authentic. If you also don’t like the traffic, tell me that! Don’t pretend to have a different opinion just for the sake of a conversation. Because I promise you, if you agree with me about the traffic, we can move on from that topic and have a wonderful conversation about literally anything else.

So what are your thoughts on this? Are you a Devil’s Advocate yourself (side note, if you are, take the Myers Briggs quiz because you’re probably an ENTP). Do you find the habit annoying, or intriguing? I would love to hear them!

And in the meantime, I’m going to buy Ace a drink this weekend for featuring him in this blog post. But we’re going to the friendliest, most accommodating restaurant in the god damn city.

Cheers,
S