My chat with stand-up comedian Stef Dag, the Hot & Single host getting people laid in NYC

By Charlie Sawyer

Updated Jun 29, 2023 at 10:59 AM

Reading time: 7 minutes

It’s 4 pm on a Friday, I’ve had a sip or two of Sauvignon Blanc, and I’m getting ready to sit down for my Zoom call with stand-up comedian and content creator Stephanie D’Agostini—or as she’s known online, Stef. And before I hear any tuts about me sampling some chilled vino before interviewing a big time creator, it’s definitely what she would’ve wanted.

I’ve been wanting to chat with Stef for some time now. Despite the fact that we’re only six months into 2023, Stef’s already become a staple within the online comedic space as well as the New York City stand-up scene—and that’s not even including the impressive recognition she’s had as a comedic sketch writer, journalist, and video director in previous years.

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One of my favourite things about modern-day girlies, especially those who operate within a comedic setting, is their ability to disarm audiences, particularly male audiences. For so long, we were fed this idea of the classic “female comic” trope. It was an archetype which was deeply entrenched in this notion that women were not only incapable of being authentically funny, but that even if they could tell a joke or two, it would only ever cater to female audiences. And that’s of course not even getting into the gender constructs which to this day impact femme-presenting and non-binary entertainers.

Stef is naturally funny, and yes, her humour is rooted in her experience as a woman, but she’s also just inherently jokes. As we began chatting, one of the first things I wanted to ask her was how she feels the stand-up space has changed and what it is about that change that’s helped diversify the inner sanctum, if you will.

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“I think what’s cool about stand-up now is that so many people are doing so many different kinds of projects. So, 10 years ago, stand-up was the avenue that everyone was taking to get noticed, but now people are doing digital stuff—and I think it’s partially because stand-up can be very exhausting and time-consuming, with little reward for a lot of people,” Stef explained.

The creator also mentioned this concept of a “tent-pole” comedian, in other words, someone who financially holds up a particular comedy club or venue, subsequently making it more difficult for newer acts to get a look in.

Stef continued: “It’s been cool to see the shift in that everyone can find their own audience which is really nice. You don’t have to become a club comic.”

Another big thing for me was finding out who exactly it was that first inspired Stef to get into the comedy game. Some of us obsessed over Tina Fey, while others were hooked on all-things Absolutely Fabulous—I might’ve been born in 1999, but reruns exist, okay? For Stef, her first comedic love came in the form of American comedian Amy Schumer. Divisive as she might be, Schumer did play a role in shifting the way women in comedy were received.

Whenever women have told what society would deem as a “dirty joke,” one of two things happen. They’re either written off as some foul-mouthed diva whose only shot at being funny is by telling a cheap joke, or they’re pigeonholed as the “sex” comedian. Schumer’s comedy series Inside Amy Schumer definitely included some pretty iconic episodes like the Last F**kable Day segment, but it also highlighted the fact that women are absolutely capable of  holding their own on screen.

Other comedians who helped shape this new era are people like Mindy Kaling and Tiffany Haddish, both female comics who didn’t shy away from the more explicit content and were trailblazers in their own right. Oh, Stef’s also a superfan of Phoebe Waller-Bridge—any Fleabag fan is a friend of mine.

Stef’s carried on this idea, with one of my favourite videos of hers being titled: ‘Quizzing my guy friends about v*ginas.’

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I mean, in general, I’m a fan of all the content Stef creates in which I get to watch men struggle. What can I say, I’m just like every other modern-day girlie.

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The next thing Stef and I jumped into was her career background and which of her previous or current projects fed her the most creatively, aka, I was asking her to choose her favourite child. As someone who grew up wanting to be a serious actor, “win an Oscar for a Disney Channel original movie” and only got into stand-up for a “dare,” Stef has an extensive and insanely impressive portfolio.

Some of the creator’s career highlights definitely includes her newsletter, or as she sees it, “a place where it gives me the space to not just be funny. I can write about an actual experience I have and be funny within it, but humour isn’t the end goal.”

Another serious career peak, and the avenue which first introduced me to Stef, is the TikTok digital series Hot & Single, wherein the comedian (as the host) interviews a plethora of different eligible individuals and finds out why they’re single and, most importantly, if they’re the problem. The entire show, which is produced and platformed by Overheard New York, feels like a conversation which could play out on a friend’s sofa after one too many Aperols, and the reason why it’s so entertaining and authentic is because Stef as the interviewer puts herself in as vulnerable position as the person being interviewed.

@ohhotandsingle

Find the love of your life at Club Nowhere, open 0 days a week. #hotandsingle #hotandsingleouttakes #overheard @stefdag

♬ original sound - Hot & Single - Hot & Single

Yes, we hear funny stories and anecdotes from the central subject, but Stef also lets people in, she tells jokes and gives us a glimpse into her life in a way that immediately makes viewers feel a part of the joke.

Sadly, however, TikTok and online media can be a double-edged sword. It can propel you up, and then drag you right back down, and Stef knows this: “It’s hot right now, but i’m excited to see how it evolves and what else this show and community becomes. I try not to be too attached to it and just enjoy it for what it is right now.”

Throughout our conversation, it dawns on me that Stef really doesn’t have too much of an idea of how popular she truly is. When we speak about my own personal obsession with Hot & Single, she looks genuinely surprised, as if she can’t fathom the idea that the show she created and hosts is internationally loved online. Don’t worry though, I think I told her a creepy amount of times how much I love it.

@ohhotandsingle

Meet CJ. They're a polyamorous double scorpio looking for someone to be a parent to their toothless cat. #hotandsingle #overheard @stefdag

♬ original sound - Hot & Single - Hot & Single

Speaking about how the show first came to be, Stef explained: “So, I was basically hired by Overheard as a Senior Creative and to jumpstart their video department because I had been directing videos previously somewhere else. And so I had a bunch of show ideas that I was like down to do and I didn’t necessarily want to do dating, I was down to do dating but I was a little afraid of pigeonholing myself into dating. I’ll do a car show next. Overheard has a newsletter and it had a segment called Hot & Single and it was big each week. They would post about some subscriber who’d written in and then people would respond and write in to date them. So, I thought ‘What if this was the idea?’ but there are so many men on the street shows, it’s truly an epidemic of its own kind. Obviously, I didn’t want to add more to this.”

“Most men on the street shows are montage, videos of a bunch of people saying three lines and you’re just trying to get a funny sound bite out of it. And the host is really just like a vessel, the host doesn’t really add anything to it. So, I wanted this one to be more intimate. I wanted people to leave the video kind of knowing who the person was. I wanted to definitely put my own two cents in. Then once we started doing it for a while, I realised there’s also this matchmaking element. What if people actually go out and then that kind of got me excited because if I get one person laid, that’s sick,” she continued.

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And if anyone was wondering if it gets flirty in the park, we have a confirmation straight from the director herself that it does: “I think the original idea when I pitched the show was ‘let’s do a dating profile in real life’ because I was on dating apps the last two years, very passively, and I just thought we’re all broken and we’re all bad at flirting and creating human connections in person. So, this was my attempt to remedy that I guess, because I’m sitting this close to people and almost harassing them a little bit and it disarms them. And I like that.”

@ohhotandsingle

MEET AJ, the gentle dom who just wants to be ignored. #hotandsingle #overheard

♬ original sound - Hot & Single

After informing Stef that the Hot & Single background audio is as catchy as any Hans Zimmer soundtrack, and buzzing with excitement over the fact that the show is now travelling to Los Angeles to film episodes and could potentially be going international in Barcelona, we moved on to what her advice would be for anyone, particularly any young women, wanting to get into the comedy space.

“I don’t do this anymore, but in my early 20s, I would think ‘Alright, I’m gonna write ten new jokes every day. I’m gonna write four sketch ideas. I’m gonna write a packet for TV.’ And it was probably the worst things I’ve ever written in my life, those need to be burned. But I guess that instills some sort of discipline, you have to have discipline, even though it’s fucking comedy,” Stef explained.

“I think anyone can do it, but you have to do it. The number one thing I hear when I’m on a date with a guy is ‘I’ve always thought about doing stand-up.’ But it’s like okay, go do it. Get up tonight and go do it. My advice is just to get up and do it. Whatever you’ve been talking about for five years, just do it. Stop talking about it.”

And she’s right. There are way too many 17-year-old TikTokers out there for any of us to stay sat on our arses, wasting away those few last precious years of youth we have left.

In terms of what’s next, I mean the possibilities are endless—the girl is literally only 27 years old. However, she might be coming to a TV or potentially bookstore near you very soon. Talking to me about a long-term project she’s been working on, Stef explained: “It started off as a YouTube video and then it became a digital idea. And then I was gonna write a book and now it’s a TV show. So, finally, when I give birth to it, whatever form it comes out as, I think that’ll be the scariest thing, when it’s over. I’ll be ‘Whoa, what do I do now?’ That’s been my guiding light for so many years.”

There was really only one appropriate way to wrap things up. I needed to find out about Stef’s recent trip to Europe, her thoughts on European men, and most importantly, why it’s so important to have at least one sultry summer under the sun.

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Her conclusion? European men are harder to be silly with (probably because Google translate can be a massive cockblock), there aren’t enough public toilets, and, last but not least “every girl NEEDS a slutty summer in Italy. It builds character and should be paid for by the government. Some countries send their young men to mandatory combat training when they’re 18, why can’t we send our girls to Italy?”

And while not everyone might be able to live out a Lizzie McGuire fantasy and ride around Rome with an inappropriately-aged fake popstar, you will probably be able to find a 5 ft 7 Italian stallion to spend some time with. And, as Stef graciously reminds me, “they have better personalities anyway.”

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