The man who made a business out of breakups

A new play debuting at this year’s Capital Fringe Festival combines real-life DC dating tales with the story of those who outsourced their breakups to one man — the Heartbreak Hitman.

Lily Strelich
730DC
5 min readJul 12, 2018

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Who among us has not been a veritable breakup doula for close friends? What if you could get paid for that service? Jonathan Kiekbusch was a savvy entrepreneur who got paid to break up people’s relationships for them, and his story was covered in an NPR Snap Judgement segment that aired in 2014. Writer Leigh Giangreco heard that segment and knew right away it would make perfect fodder for a romantic comedy.

Four years later, her play “Heartbreak Hitman” debuts at Capital Fringe Festival on July 20, a rom-com combination of “Up in the Air” and “Hitch.” We caught up with Leigh about channeling Nora Ephron, canvassing DC neighborhoods for juicy breakup stories, and why City Center is the best breakup spot in the city.

Writer and director Leigh Giangreco (right) instructs Will MacLeod.

How did you first hear about this story and how did you determine that a play was the best way to tell it?

I was just doing some cleaning around the house and had the radio on WAMU when I heard this story. The way Jonathan told it, it just sounded made for a rom-com and for some reason I thought, “I’d love to write this.”

Originally, I was writing a movie, but reality quickly caught up with me and I decided to start small — a Fringe play seemed like a logical first step.

You chose to set it in DC in order to write this city a love letter the way Nora Ephron (all hail) wrote about New York. How did you go about doing that?

I’ve always felt DC got the short end of the stick when it comes to movies — especially rom-coms. There’s “The More the Merrier” from 1943 and “Born Yesterday” from 1950, but after that, the most love DC gets on the silver screen is some cheap flyover shot of the Capitol in a Michael Bay movie.

New York is always cast as this romantic city, but Ephron herself curses Washington in her roman à clef, “Heartburn.” I love DC in the same way Ephron loved New York, so I studied the way she portrayed her favorite city in her films and books. Setting is so important in her movies that it nearly functions like a character itself. This is especially true in “You’ve Got Mail.” If you watch the movie (and the commentary from Ephron like I did!), you’ll see how she wanted to paint New York — and particularly the Upper West Side — as a village or a small town. She does this by pointing out small quirks like the airborne bagel flour that never really settles, or staging a tiff between Tom Hanks and Meg Ryan at Zabar’s.

Even though my play is about breakups, it’s also my love letter to DC. So we start off in a federal building, to represent the caricature of soulless Washington that probably comes to mind for people who don’t live here. But each place Jo and Jon visit is meant to peel back another layer of the city and show the audience how much life and romance there is here. So we go to Yum’s and taste mumbo sauce, we squeeze between the bookcases at Capitol Hill Books, we dance at Jazz in the Garden. To me, each of those places shows a particular quirk of DC.

We go to Yum’s and taste mumbo sauce, we squeeze between the bookcases at Capitol Hill Books, we dance at Jazz in the Garden. To me, each of those places shows a particular quirk of DC.

Capitol Hill Books is this crusty jewel of organized chaos and its close quarters especially appealed to me for a rom-com scene. I find bookstores so romantic because when you think about it, a book is like a horcrux where each one you pick up reveals a little piece of your soul. It’s the perfect way to introduce our romantic leads to each other and to the audience.

Eliza, played by Katie Kramer, and Sam, played by Jeronique Bartley, have a couple’s quarrel.

You also canvassed the city for real-life local breakup stories to include in the play — what was that process like? What did you learn about DC dating that you weren’t expecting to?

I started that process after Maryam Fatima Foye, artistic director of the Hissing Black Cat Theater Company in Anacostia, read my script. She liked it, but she noted how many of the characters sounded the same. I realized I needed fresh voices and different perspectives, so I did what any journalist in need of a good quote would do: I went out and conducted man-on-the-street interviews.

I literally just biked and walked all around DC — from Anacostia to Navy Yard, Brookland to Shaw, Columbia Heights to Dupont Circle. I’m a journalist by day, so I have no qualms about talking to strangers. I had a little more trepidation with this assignment, but surprisingly, few people rebuffed me. Instead, I think I ended up functioning as a free therapist for many of the people that I interviewed.

Sam, played by Jeronique Bartley, comforts her friend Jon (Walter Riddle)

I think I ended up functioning as a free therapist for many of the people that I interviewed.

But DC breakups aren’t unique (maybe with the exception of the woman who found out her boyfriend was a closet conservative). I expected to find differences between ages, neighborhoods, wealth and professions, but you realize the universality of breakups. You can’t buy time to heal from a heartbreak and age doesn’t always equal wisdom in love.

What’s the best breakup spot in DC?

I guess that would depend on what kind of breakup it is! I wouldn’t want to ruin a spot I love, so I would never break up with someone on Capitol Hill, the National Cathedral, or Meridian Hill Park. All of those spots are too lovely for a breakup. It would have to be somewhere completely soulless, so…probably City Center, which I avoid at all costs. The HUD building also has an appropriate, dark milieu too for a breakup, but I still respect Marcel Breuer’s Brutalist architecture more than City Center.

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