Mary Beth Barone Is Here to Save Your Dating Life


Mary Beth Barone is out here doing the good work. After years navigating the New York City dating scene and racking up countless horror stories, she set out on a mission: to rid men and women of their fuckboy tendencies. She swears by her six-step treatment program. Barone outlines her rehabilitation process in Drag His Ass, the comedy show she created in 2019. The concept was an instant hit. Women came out in droves to see Barone’s showcase, which included guest comedians trading relatable dating stories, multiple segments, and hilarious fuckboy trivia. It was so successful (like "selling out venues nationwide” successful) that Comedy Central partnered with the 29-year-old to turn the show into a web series, which premiered earlier this month. Each bite-size episode finds Barone tackling a different toxic habit—such as ghosting, serial dating, and cheating—while dishing out expert advice with her signature dry wit. 

If she isn’t already, Barone should definitely be on your radar. I’m not just saying this because she is the deadpan darling of NYC’s comedy scene with a serious Ashley and Mary-Kate Olsen obsession. I am saying it because she is also curating some of the best laugh-out-loud content out there. There’s the aforementioned Drag His Ass and corresponding meme-filled Instagram account, her regular stand-up specials, and the podcast Obsessed she co-hosts with fellow comedian and internet personality Benito Skinner (aka BennyDrama)—it’s their pop culture take on everything from true-crime makeup to the Kardashian legacy. Barone has been busy in quarantine, and we’re reaping the benefits. 

Curious to know Barone’s thoughts on everything from what not to wear on a date to her favorite Olsens style moment (hint: it comes from Passport to Paris), I jumped on a Zoom call with the comedian. The conversation that ensued is not to be missed! 


(Image credit: Corbin Chase; STYLING: Betsey Johnson dress from @malinlandaeusvintage; Tiffany & Co. bracelet)

Congratulations on Drag His Ass! Where did you get the idea to do a show like this? 

Well, I am a self-described fuckboy addict. At one point, I wasn’t really happy with my dating habits, and I found myself veering into fuckboy territory. I needed to evaluate what I was doing and figure out how to get better results. So I decided that I was going to start keeping track of the number of days I went fuckboy-free on a whiteboard in my apartment. It was in the living room, and my roommates were very supportive of my mission to make it to 100 days. I would update social media with my progress, and I got a really good response from people encouraging me and also being like, "I need to do this.” Eventually, I was like, "You know what, this is a universal thing that people are dealing with right now (and this was like 2019). I’m going to do a show and call it Drag His Ass. It’s going to be a live show, and I will invite other comedians to come on and talk about their dating experiences. I will talk about my six-step process toward rehabilitating yourself if you are also a fuckboy addict,” and then I did some fuckboy trivia and different segments, and it was super fun. The show sold out, and the audience was almost completely women, and I felt like it was good energy and something that people really wanted. From there, I moved the show to a bigger venue in Manhattan, and every single show we did there sold out. It was gaining momentum, and early on, I started an Instagram for it. I had no idea if people would like it, but there are so many tweets and memes about dating and how bad it is, so I was like, "I might as well compile them all into one place.” A lot of times, I think about, Am I just contributing to the noise online? Is this actually a good thing? But when we get messages from people being like "This is my favorite Instagram” and "I come here and feel so much better and laugh so much,” that makes it definitely worth it. From there, we decided to pitch it as a show. A lot of networks saw it as risky, especially with the title Drag His Ass. Comedy Central said they wanted to do it as a digital series, and I’m actually so happy that that’s how it turned out because I think we were able to do a lot that we wouldn’t have been able to do on TV, including keeping the name. I just feel there is a lot more oversight on TV, whereas digital is the Wild West. I was actually very pleased with how it came out. 

So did you make it to your goal of 100 days?

I had some relapses. Relapse is step three in my six-step process to recovery because you are going to relapse, and that’s okay. But now, I can confidently say that I am… Let’s see. I remember the exact day when I relapsed last. I am 478 days fuckboy-free. The program works is what I am saying. 


(Image credit: Corbin Chase; STYLING: Mia Vesper top; Levi's jeans)

In one of the episodes you say, "When I see a guy in a beanie, my first thought is, What’s he hiding?” In your opinion, what are some other alarming fashion choices?

In my intro for my live show, I go through the fuckboy starter pack, and that includes joggers, vaping at formal events, which I do consider a vape an accessory, so if they are vaping out in public or at the Oscars, for example, that is a red flag to me. Wearing a huge watch. I don’t know why, but they love to have a huge watch. Also, when they have that very defined, pronounced line in their haircut. And then, I would say for women fedoras—I had a personal experience with one, so that’s something I am going to avoid—and a lot of bracelets. For girls, it’s stick-and-poke tattoos, and for guys, it’s thigh tattoos. Just be weary. I am not saying anyone that has those things is bad, but I am saying there might be a higher chance, and that’s just based on qualitative data. 

On the flip side of that, what, in your opinion, makes for a foolproof first-date look?

Okay, a foolproof first-date look. I just posted someone’s tweet about this on @DragHisAss. Dressing well as a guy is literally so easy. Wear Converse, straight-leg jeans—not skinny jeans but straight-leg jeans—and either a button-down or a collared shirt or even a black T-shirt. Just show that you put in a little effort without raising any red flags. I think girls have a lot more options because guys don’t look for red flags because maybe girls are just better, but I’m not sure. It’s so tough because I really wasn’t dating much at all before the pandemic, but it depends. When I am going on a date with a girl, I can wear spandex shorts and a crop top with a crossbody bag with my sneakers. Dates with a guy, you gotta really dumb it down, like jeans and a blouse. See, the thing with guys is they get very confused by fashion. So if you are going to a bar to try and meet a guy, it’s good to wear things that confuse them. It’s as simple as painting one nail a different color than the rest. A guy will ask you about that and try to parse out some kind of meaning. So that’s a good conversation starter. 

I want to talk about your stand-up. How would you describe your comedy style? 

Dry. I would say very deadpan. I think it’s social commentary and speaking about my experiences as a young woman living in a big city and just trying to make those things funny. One time, Time Out New York said it was "dark postmodernism,” and I think I clung onto that because it sounds smart but also because I looked up what postmodernism is, and it is accurate. 

At what point did you realize you could make this your career?

My gateway drug [to comedy] was doing improv at Upright Citizens Brigade. I was doing that for a couple months before I bought a little notebook and started writing things down. I was watching a lot of comedy and trying to absorb as much as I could, and I said, "You know what, I’m going to do an open mic at UCB.” It was an all-women’s open mic. You spend two minutes on stage, which is still so terrifying even though it’s 120 seconds. I pretty much said before I went up there, "If I bomb, I will never do it again,” and then, my set went so well. As soon as I got off stage, I was like, "Okay, I think I just found the thing I need to do.” It was that high that you then keep chasing. I think there is a certain level of delusion to setting out to be a successful comedian, and I think I had just the right amount of delusion. 


(Image credit: Corbin Chase; STYLING: Helena Magdalena dress; vintage boots from @malinlandaeusvintage)

Can you walk me through preparing for one of your sets?

I have my tiny notebook. I have so many tiny notebooks. If you see my desk at home, I have a box full of them. I always carry a tiny notebook with me, and the smaller the notebook the better. I usually will write things down that I think are funny. Usually what I’ll try to do for new jokes or a new section, I will try to work them into an existing set. Going up with completely new material for like eight minutes can be a little scary because if it’s all not good, then it’s really not good. So I try to fold it into things that already exist or have been tested. I think what’s nice for me, in terms of adding new bits into existing material, is that all of my observations are pretty distinct and pretty specific, but I can usually piece things together thematically pretty well. I try to be thoughtful about structuring it because there are only so many formats of jokes. When I was planning my The Tonight Show set, I was like, "There is too much misdirection.” Misdirection is really easy to start relying on because you are basically either setting something up and saying something unexpected or you are listing out three things, and the third thing is not like the first two. I don’t want to rest on that because usually you will get a laugh, but I want to know looking back on a set that I challenged myself to have different joke structures. 

You have talked about how special performing live is to you. After a year of quarantine, do you have any live shows coming up that you are looking forward to?

I am dipping my toe back in the water. I did a few shows to prepare for the two film sets that I’ve done in quarantine, for Comedy Central and for The Tonight Show, and it was so nice to brush off the dust and prep for those sets. In October when I was prepping for Comedy Central, I was so paranoid. They were all outdoor shows, but if the mic would touch my mouth, I would put hand sanitizer on my mouth, which I don’t think you are supposed to do. I am pretty sure it’s poison. I was like, "This probably isn’t worth it to keep doing until it’s safer.” So now, I’m slowly starting to schedule outdoor shows. I think I might do an outdoor Drag His Ass this summer. That would be the goal.

You were just in Los Angeles co-hosting an Oscars watch party with your good friend Benito Skinner aka BennyDrama. Who had some of your favorite looks of the evening?

I would say LaKeith Stanfield just blew everyone else away. To me, that was definitely the best look of the night. I think Regina King looked amazing. I love a two-piece, so Carey Mulligan. Even though I think the dress read orange in photos, what I was hearing from the troops on the ground was that it was gold. And that’s an important distinction. I like people who wear crop tops to the Oscars because if I ever go, that would be the plan. I also liked Laura Dern’s dress. It was very risky, and I love a bold feathered number.


(Image credit: Corbin Chase; STYLING: Tyrell top and skirt exclusively @thebreak; vintage heels from @malinlandaeusvintage)

You and Benito host a podcast together called Obsessed, where you talk about everything from Mary-Kate and Ashley Olsen’s career to being left on read by Ariana Grande, and you’ve also done some shows together. Where did your friendship begin, and what do you love about collaborating with him? 

So Benito and I, like all great romances, met at a comedy show. It was at a bar in Bushwick, and we gave each other the eyes. It was like life and fate will bring us together again, and low and behold, it did. We stopped and chatted quickly that night, too, but then, we had a show in a clothing store in Brooklyn, and the green room was the stock room, and sparks flew. We were like, "We need to work together,” and then, we made the JVN as Jesus video, which was obviously an amazing start to any working relationship. It’s nice to have people who you are unconditionally happy for and want to see succeed, and their triumphs feel like your own because you just love them so much. I think those are things that are hard to find in a really competitive business. But I definitely have that with Benito and a handful of other people, and it’s so valuable. They are really the only ones you can commiserate with because they really understand how things work in comedy, which it’s all very messed up. So it’s really amazing. 

I want to go back to Mary-Kate and Ashley for a moment because you are a pretty big fan. In terms of style, would you say you are more of a Mary-Kate or an Ashley? 

I’m a Gemini, so I’m going to do a cop-out and say I’m both because I feel like Mary-Kate was always positioned as the sporty tomboy, and Ashley was the fashionista, but I think there is room for both. They were such style icons to girls our age. I remember being at the mall, and I just wanted those really round, oval-shape sunglasses, and my mom bought them for me. They were purple lenses, and I just saw them on Ray-Ban for sale, and I might just get them. You watch it back now, and some of their looks really do hold up. 

Do you have a favorite look of theirs?

It’s probably going to be Passport to Paris. That was the moment for me. There is one day where they go to the Louvre, and I can’t remember if it’s Mary-Kate or Ashley, but she wears a peasant top and light jeans and maybe one of those bandanas tied around her head. For me, that’s peak. I just bought a peasant top like that at Brandy Melville. 

They did not miss. When I think about what shaped me as a kid and why I’m like this, I really think it’s Mary-Kate and Ashley and Posh Spice. When you watch the videos of them, they are so dead-eyed, but I think that’s probably how people see me sometimes. 

What did you think of Victoria Beckham’s response to Justin Bieber sending her Crocs?

I miss when we could speak in hyperbole like that, but we can’t really do that anymore. But Victoria Beckham can say she would rather die than wear Crocs Justin Bieber gave her.


(Image credit: Corbin Chase; STYLING: Helena Magdalena pants; vintage earrings from @malinlandaeusvintage)

What is your day-to-day style like? 

I would say, most of the time, you’ll catch me wearing some shade of white crop top with jeans and my white Air Force 1s. At my age, 29, I want to find that balance of comfort and style, and I really subscribe to [the idea that] if you look good you’ll feel good. I just went to Proenza [Schouler] on Greenwich Avenue yesterday because I tried on a dress last week and couldn’t stop thinking about it. It’s a little white, almost-peasant dress. It looks like I’m trying to lure you into my cult in Midsommar. I am just ready to wear that out in the day and feel amazing. Usually when I have a really long weekend of working or work really hard on something, I will go buy something. I think, too, as I’ve grown up, besides Brandy Melville, I really do invest in things that I think are classic pieces I will have for a long time. 

What about your stand-up style? Does the aesthetic change at all?

It’s a bit different. For stand-up, I guess it is streetwear but fashion streetwear. What I’ve had to learn throughout the years of performing is that what you are wearing says so much about you to the audience before you even open your mouth. You don’t want to alienate them. You don’t want to look like you think you’re better than them, or they will hate you. I find that brands like Nike, Adidas, things like that feel more approachable than wearing Gucci pants. If it’s a fancy show, I will play that up a bit more with what I’m wearing. For a long time, there was this theory that you can’t show legs in stand-up. You’re supposed to wear pants. But if it’s hot, I’m going to maybe wear shorts or a pleated skirt. Essentially, when you step on stage, your outfit is presenting who you are before you speak, so you want to be intentional so that people make the assumptions you want them to make. 

Drag His Ass is now streaming on YouTube. 

Photographer: Corbin Chase

Stylist: Meredith King

Makeup Artist and Hairstylist: Mary Beth Barone

Executive Director, Entertainment

Jessica Baker is Who What Wear’s Executive Director, Entertainment, where she ideates, books, writes, and edits celebrity and entertainment features.