Let Me Break You Up’s Carly Ann Filbin talks petty couples and the Brooklyn dating scene

Dating is really, really hard, especially when you’re surrounded by social media’s illusion that everyone but you is deeply in love, on a beach, self-actualized and blissfully happy. Cleveland-born, Brooklyn-based comedian/writer/actor Carly Ann Filbin realizes this, and has capitalized on the building cynicism to create “the world’s only break up show,” Let Me Break You Up: An Anti-Dating Gameshow.

When she’s not destroying relationships (not really though, there’s way more to it than the name), she’s starring in her web series Single Blonde Failure, investigating what the most overrated sex position is and doing financial planning for those of us who can’t stop spending vital rent money on takeout on her CNBC series Saved – not to mention drinking bleach, “so she can be blonde on the inside.” Now that’s commitment.

We spoke to Carly about petty couples, sex, social media and why Williamsburg is better to be single in.

Let Me Break You Up turns two years old next month! What can folks expect in year three? 
Wow. Ok. Well, I think in year three it’s gonna get bigger in ways no one ever dreamt of. I think I’m going to have bigger fights on stage, bigger celebrities do it; by the end of year three I definitely think it’s gonna be a TV show. It’s gonna get bigger, badder, better. It’s slowly been getting more popular. I just want more people to see it.

And what’s the most golden nugget of relationship advice you’ve learned from the first two years?
I would say, let it go. you’d be so surprised about what people are really holding on to. One of the questions I ask is where would your partner take ME on my first date? And often people answer where he took them on the first date, and if something bad happened on that date yearsss ago, they bring it up, they haven’t let it go. So many arguments on my show, they’re bickering, something’s happened in the past and they can’t let it go.

Always have a mindset of forward momentum, keep on trudging, and that little thing that’s annoying you will pass. People are weighed down by bags of pebbles! It’s like, “A year ago when we went out for dinner with my parents I felt like you were putting too much sugar in your coffee and no one knew it but you.” The partner was like, “What are you talking about?”

If you go to watch it and you’re in a relationship, you feel good about the hardships you have in your relationship. If you’re single and you go to watch it you’re like, I’m so glad I don’t have to deal with this bullshit. It just makes everyone feel good about where they are. I’m biased, of course.

How many couples have you actually broken up, would you guesstimate?
Ok, so, I’ve been doing it for two years almost and I know that only two couples have broken up, months after the show. So what happens is, couples come on my show and it brings them together. It’s a shared experience that they’re able to laugh at. I haven’t created any relationships, but I feel like I strengthened all of them.

I book the couples beforehand. There are a few couples that come to me after the show and want to volunteer, but nobody is coming to make a public embarrassment of their partner, and I’m happy about that.

Do you truly believe love sucks? Are we living in a post-love world?
Ya, I don’t believe that, but it is really fucking hard and we’ve gotta laugh about. I say it at the beginning of the show, but the prize at these shows is getting to date someone. Which is never a prize. It’s really sad and lonely and I feel like I have to laugh about it. The host is definitely a caricature of myself, the very, very bitter side. And when I started the show I was very bitter. If someone would talk about their engagement around me I would get up and leave. The show has sparked my faith in relationships because I see these couples laugh about themselves after the show and thank me. So, I don’t really believe it, but it’s very hard for me.

One time I did this show literally a week after I was dumped and I started crying on stage. I think the audience thought I was laughing.


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What dating game show inspired you the most?
Definitely The Newlywed Game. That’s what my show is, it’s a take on The Newlywed Game. When I was younger, I was obsessed with Room RaidersNextParental Control. I guess I must’ve been in elementary school and there was a show called Stud, I would watch it every night in the summer and my parents banned me from it. I can’t exactly remember the format of it, it was like The Dating Game. I was obsessed with all those shows. I got asked to be on ElimiDate but I was underage (you have to be 21).

All of them together, that was my culture growing up. I just loved them. But now it’s definitely The Newlywed Game. The original Newlywed Game is obviously heteronormative but also misogynistic and so many of the questions are designed to make the woman in the relationship feel bad about themselves. I just wanted to do it justice, I love this format, I wanted to make it more Millennial, more appropriate for the people who’d be watching or playing today. My questions are pretty universal for people who are dating; anyone who is in a union will be able to answer.

How long have you been in Brooklyn?
About five years, I think? I lived in Williamsburg and then I lived in South Slope.

Which one has been better for being single? 
I think definitely probably Williamsburg. Almost no neighborhoods are good for dating, but Williamsburg is good for hookups. And Park Slope is good for peace and quiet and if you wanna fall asleep at a decent hour.


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Are certain neighborhoods actually worse to be single in, or is that too specific in a city where you can get around fairly easily?
I know a couple people who’ve met at bars. I would think the areas with the most bars, that have things that draw people out are good. I guess, that being said, Prospect Park is huge and you could just meet someone in the park. But I think when it comes to dating it’s where you feel comfortable putting yourself out there. There’s a million people out there like “where are all the single people” but it’s really about being where you feel comfortable.

What’s worse for being single, New York or social media?
Social media five million percent. You can be single in New York and still have a good time. You can at least look at hot people even if they’re not sitting with you. Social media, everyone’s putting on their best face, they’re putting up their own perfect story, and you’re watching it as a perfect story. About two years ago, I had a really bad social media problem and went to therapy and the therapist said every single patient had a problem with social media.


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And what about the dating apps, would you count that as social media?
I was really thinking of Facebook, Twitter, Instagram, definitely the dating apps are an extension now.

I think the dating apps, they, for me personally, they take the place of mindless time taken on social media. When I’m on dating apps, it’s like oh, I have five minutes, I wanna be on my phone, so it’s taken less seriously. I think it’s like, just your intentions. If you’re honest, this might work it might not, if you’re on it, and like oh, this is a waste of time, then it is a waste of time.

I’m in a very hippie dippy phase of my life right now.

Do you think New York is a miserable place to date or slightly better than the rest of the world? I’m not even sure which is the more popular stereotype.
I feel like…that’s hard to answer. People don’t move to New York, they’re not like “I’m packing my bags, I’m going to New York, I’m gonna find love.” People are like, I’m the best of the best, and I’m gonna make it in the big city. I feel like relationships are never the priority. That being said, there’s so many things to do, there’s so many people here, and we all are kind of like-minded here, we want to make the most out of our lives. If you can find a good person to date, I feel like the city is your oyster. I feel like it’s hard to find a good person to date.

I did my show in Cleveland. I’m from Cleveland. The dating in a smalltown, I feel like life is less competitive. It’s like, ok, what do you want to do? Be a a teacher, great. You accomplish that when you’re 23. And it’s like ok, what else? People are more prone to settling down. It’s less stressful. There are less cool people, there are less opportunities. It’s more competitive here. But it all comes down to mindset.

Is there a difference doing comedy in Brooklyn versus doing comedy in Manhattan?
Hmmm. No. I don’t think so. I think everyone just wants to go out and laugh. I don’t think there’s a difference. I think there’s a difference in the different scenes, like the very alt Brooklyn comedy scene and the commercial comedy scene, like UCB. I feel like I’m in both. The crowd is expecting something different, maybe something a bit weirder in Brooklyn, but mainly the people just wanna laugh.

Last, but certainly not most least: What is the most overrated sex position?
I’m gonna say this and I know this is against popular opinion: I think doggy style. It creates a lack of intimacy. As for underrated, I don’t even know what you would call this, but one time I was on my side, kind of like curled up and he was straight over me, like missionary, but I was on my side.

The next Let Me Break You Up will be at midnight on Friday, August 18th at UCB East. Tickets are $7.

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