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Jaboukie Young-White on weird dating habits, playing straight and being Internet famous

The Washington Post logo The Washington Post 9/9/2021 Sonia Rao
a person posing for the camera: Comedian Jaboukie Young-White becomes a leading man with the new romantic comedy “Dating and New York.” (IFC Films) Comedian Jaboukie Young-White becomes a leading man with the new romantic comedy “Dating and New York.” (IFC Films)

Jaboukie Young-White is a master of disguise. If you were to happen upon his popular Twitter account without any notion of who he is, you might believe him to be a young man named Giabuchi with an extraordinary passion for his Italian American heritage. If you visited his profile before he was suspended on Martin Luther King Jr. Day last year, you might have done a double-take at the sight of a verified account with “FBI” as its display name tweeting, “Just because we killed MLK doesn’t mean we can’t miss him.”

In reality, Young-White, a 27-year-old comedian raised in Illinois by Jamaican immigrants, just excels at trolling. His unconventional approach to social media has earned him nearly 900,000 Twitter followers, plus a fan account that keeps track of his deleted tweets. He brings that same energy to his comedy, whether with stand-up sets, TV writing gigs or his work as a correspondent on “The Daily Show.”

Young-White’s latest project embraces his natural ability to shape-shift. In his largest acting role yet, he plays a lead in the new romantic comedy “Dating and New York,” about a romantic millennial man and a more practical-minded woman (Francesca Reale) who meet on a dating app and decide to become friends with benefits.

It’s somewhat of an unexpected role for Young-White, who often tweets and performs stand-up about his experiences as a gay man. (His first set on “The Tonight Show” involved his passing as straight: “I’ve been told that I can come across as ‘masc,’ and if you don’t know what that means it’s basically just gay for, ‘I’m not like other girls,'" he joked.) But then again, Young-White is all about surprises.

He recently chatted with The Washington Post over Zoom about the movie, his dating life and what it’s like to be Internet famous.

This interview has been condensed and edited for clarity.

Q: What drew you to this role?

A: It really felt like a departure from a lot of the things that were brought in my direction … even the fact of playing a romantic lead in a straight rom-com.

I feel like when you think of someone wanting to experiment and do something out of the ordinary, them doing a fun rom-com wouldn’t be that. But for me, it was. … I also just genuinely love rom-coms. I feel like there’s been such a dearth over the past couple of years or so. My teenage self was obsessed with rom-coms. I cannot name how many rom-coms I watched on, like, Putlocker and 123Movies.

Q: Wow, Putlocker just took me back. I forgot that website even existed.

A: Yo, right? Exactly. That was the golden — if you had a link on Putlocker, you’re good. You might as well be watching it on Netflix. Putlocker was [mimes a chef’s kiss].

Q: Which rom-coms were you watching?

A: In high school my favorite was “Eternal Sunshine of the Spotless Mind.” You know, “500 Days of Summer” [laughs]. That was a big one. All those Tumblr-era rom-coms. “Friends With Benefits,” both the Mila Kunis and Justin Timberlake one and — I can’t remember what the other one was.

Q: Oh, I know the one you’re talking about. Two very similar movies.

A: I just tore through the genre. Also the Jim Carrey one where he plays gay. “I Love You Phillip Morris.”

Q: To go back to what you were saying earlier — and I don’t mean to ask this in a way that suggests you can’t play someone with a sexual identity different than your own — but how did you get into the mind-set of a heterosexual man? Did you get hazard pay?

A: [Laughs] That’s hilarious. For this role specifically, getting into it was interesting because with the background I come from — I’m from the Midwest — I feel like the benchmarks and standards for masculinity are so much higher and unattainable than [they are in] New York. When I first came here, I was like, “Oh my God, everyone here is gay. That’s so cool.” You’d be with someone at an event and they’d be like, “Oh, this is my partner.” And you’re like, “Oh my God, they’re gay. That’s awesome. They’re in a same-sex relationship.” And then they’re, like, a cis[gender]-het[erosexual] couple. And I’m like, “Okay, interesting, interesting.” I have to recalibrate my expectations of a straight man.

There were some things that translated and were sort of universal … and then there were other things where I was like, “You have to explain to me what this is because I’m not 100 percent sure.” With queer relationships, you’re kind of making everything up as you go. And with so many cis-het relationships, there’s a societal story and a narrative that’s laid out for you that you can easily just fall back into and follow, and let that take the wheel. You can just say, “I know I’m supposed to do this.”

What I thought was interesting about this story is that these are straight people who are trying to come up with their own outside-the-norm situation. To me, that feels really relatable.

a man and a woman sitting at a table eating food: Young-White, left, and Francesca Reale appear in “Dating and New York.” (IFC Films) Young-White, left, and Francesca Reale appear in “Dating and New York.” (IFC Films)

Q: Were there any moments in the script that particularly resonated? For me it was little things like seeing a Co-Star push notification show up on a character’s phone while they’re swiping on a dating app.

A: The breakup scene on the subway. There have been multiple times [laughs] — okay, I wouldn’t say multiple. There was one time in specific that I can remember … you get broken up with and you just start bargaining. You just start throwing out these milestones that to you were a big deal, but really at the end of the day don’t change anything. When he’s like, “You FaceTimed with my mom!” Well, Mom probably just called and they happened to be in the room and they were like, “Oh, hi, Mom.” You blow these things up into epic proportions and really stew in this sense of betrayal.

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Q: Another thing I found interesting about the movie was its inherent understanding of dating in the Internet age. That kind of understanding is part of your whole thing, too. Everyone loves your Twitter account, Instagram, all of that. What is Internet fame like? I think it can be a difficult concept for many people to grasp.

A: There was a moment in time where [my face] was my avatar on Twitter and I would post pictures of myself. And then I made a conscious decision at some point, like, I’m just going to become an entity on here. I don’t want to be a person [laughs]. Sometimes if I post a picture, I’ll get replies like, “That’s what — this is what he looks like?!” I kind of like the whole “Wizard of Oz” thing behind it.

Besides that, I would say it can be interesting. Especially with dating, there have been times when I’ve been on dates and someone will bring up something so hyper-specific and I’m like, “What are you talking about? I don’t get it — like, grapefruits?” I’m just kind of laughing along and then I’ll remember, “Oh, wait, I tweeted about grapefruits a couple of weeks ago.”

It can be interesting, weird, odd, surreal to be perceived at that level.

Q: I mean, there’s literally an account documenting your deleted tweets.

A: Exactly, exactly.

Q: Do you know who runs that account?

A: I’ve actually met that person! And they’re really cool. They’re great.

Q: Oh, yeah? What was that like? It must have been kind of strange, too.

A: I honestly was like, “You’re doing archival work, thank you.” I totally could just not delete the tweet. But at this point it adds a layer to some tweets sometimes where I’m like, this will actually be funnier as a deleted tweet.

Q: The art is the deleted tweet. We’ve talked about different parts of your career, and you’ve dabbled in all sorts of things. How would you describe your overall approach to picking projects?

A: What I try not to lose sight of is just going toward projects that feel interesting and challenge me and that subvert what is expected of me or even what’s expected of a genre. I started in comedy, and at the core of comedy is usually a reversal of expectations, or a surprise, or at its molecular level just something that tickles you. Or is odd or interesting or a little bit off the beaten road. That is always what’s going to excite me about projects. It’s that and, “Would my 12-year-old self, 16-year-old self, 20-year-old self, how would they feel about this project? Would they be excited for this?”

Q: Have you always known you wanted to work in the entertainment industry?

A: Yeah, kind of always. From a child, I used to be, like, “Why won’t my parents be stage parents? I want this so bad.” I would watch “Degrassi” and just seethe with jealousy, like, “I wish that were me.” But I’m ultimately happy it didn’t go that route because I got to just be a person for at least the first quarter of my life.

Q: What era of “Degrassi” would that have been? Was that the Drake era?

A: So it was a little bit of the Drake era going into the new, new generation … Man, after J.T. got stabbed, that rocked my world. That really rocked my world. Stuff like that, I would watch and be like, “I wish I were getting stabbed.”

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