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Bitch at Us: Bobby Gill of Cupid’s Undie Run

Let us tell you what you should be doing on February 13: running around the Washington Monument, in the snow, in your underwear, with a bunch of other crazy people. Here’s why.

For starters, it’s for charity. Bitches love fundraising. Secondly, it involves day drinking, which means mimosas. Bitches love these too. What really sealed the deal for us, though, is that the race is only 1.5 miles—and it’s not really a race at all. But a festive fun run—with breaks for photo opps and push ups for those who wish.

Lastly, you get to wear cute undies, jammies, or costumes. Cupid’s Undie Run has become a Valentine’s Day fixture of Washington, D.C. and many other cities. It’s a silly, fun charity run that supports the Children’s Tumor Foundation. It’s more of a party than a serious, competitive race that benefits cancer research.

So, if you have a boo, or are looking for one who’s fun, charitable and active—Cupid might help you find them. The Bitch team will be there, running, and fundraising—with a pre-race brunch at Lincoln.

So, register for Cupids Undie Run with the code “BWB” for 25% off and then make your reservation for the pre-race brunch at Lincoln on OpenTable. Brunch begins at 9:30 a.m. and then we head over to the race activities at 12 p.m.

But, before you brunch, allow us to tell you the story behind Cupid’s Undie Run.

We sat down with our friend, Bobby Gill, co founder and COO of Cupid’s Charities to hear what he has to say about undies, running, Cupid’s Charities,—and what you should be doing Valentine’s Day weekend.

Tell us about the start of Cupid’s Undie Run.

During the D.C. Snowmaggedon of 2010, when the city was incapacitated with snow, I received a very important email. My good friend, Brendan, sent an email to me and my roommate, Chad Leathers, proposing this idea of us getting together, drinking, running around in our underwear, and doing it all for charity.

I responded back and said, “Brendan, that’s a terrible idea. Let’s do it.”

The reason we chose the Children’s Tumor Foundation was because Chad’s younger brother, Drew, has a rare genetic disorder called Neurofibromatosis (NF). NF causes tumors to grow on the nervous system. The year 2009 was really horrible for Drew. He spent 183 days confined to a hospital bed. He was so sick he couldn’t leave the hospital or get out of bed. That was really our motivating factor to get up and do something for him and others like him.


So how did you organize the first year?

We decided that we were going to do this and basically split up the duties. Chad created the website. Brendan found a bar. I started reaching out to the local community.

We only had five weeks from concept to race day. We were expecting maybe 50 people to show up. Turns out we had 650 people show up that first year and we raised ten thousand dollars. At that point, we were like, “Holy shit. What have we done? This is awesome.”

So today, six years later and you’re in 39 cities and you’re on track to raise five million dollars.

It has been a wild few years. We’ve had an incredible growth curve that we never would have expected. We didn’t set out to do this with a business plan to strategically get us here. This success is a result of people really getting behind the concept and being really excited to experience something new, fun, and different from any other charity event out there.

It’s truly unlike any charity or running event that you might find.

D.C. was an instant hit–it got great press coverage. People from all around the country started reaching out to us saying that they wanted this in their city.

The first two years we were only in D.C. and in year three we added on five more cities and actually quintupled our fundraising. Since then, we’ve added on new cities every year. We’ve expanded and improved our fundraising tools, incentives and prizes, and what we offer for individual fundraisers. We’ve improved the party every year and strive to make it as much fun as possible.

DC 2014 - Kevin Carroll (US capitol flag)

When did you quit your job and make this your full time gig?

In February of 2013, we raised one million dollars which we hit the morning of D.C. race day. That was a moment of realization that this thing we created was something incredible and also successful. I realized that I needed to put my full self into it and I put the wheels in motion to hire myself full-time. I quit my government job, took a pay cut, and entered the non-profit world. I started working full-time for Cupid’s Charities in September 2013. (Cupid’s Charities is a 501c3 non-profit.)

You were just on the cover of Runner’s World Magazine. Tell us about that.

It is the biggest running publication in the world. I’m on the December cover and it’s the craziest thing that’s ever happened in my life. I’m not just running on the cover—I’m leaping through the air in a small pair of red undies.

The cover just happened by chance. I was browsing the internet and saw that Runner’s World was hosting a contest. So, I brought it back to the Cupid’s team and started pitching different Race Directors to see whose story would be the best fit. The team came back to me and said, “No, Bobby. You’re the founder of this. You used to be an ultra marathon runner, this is your story to tell and you need to pitch yourself.”

What sort of funny things or opportunities have come as a result of your new-found stardom?

They unveiled the cover of Runner’s World on The Today Show. So I went up to New York and was actually on TODAY. While I was waiting in the green room, Martha Stewart walked up to me and asked what I was doing there.

I told her that, “I’m going to be on the cover of Runner’s World this month. I put on a charity run where everyone runs around in their underwear to benefit NF research.”

She was having none of it. Not interested in the least bit. I tried really hard to get to run our race in her underwear but she was having none of it, because she is hard core.

D.C._JimBoswell7 (1)

Cupid’s Undie Run gets pretty wild. Tell us about your best memories from the run.

There’s one guy that comes every year. He looks a little bit like David Beckham. One year he came as a package of H&M underwear that had Beckham on them. He came as “David Beckham’s Package.” His name is Steve. It was hilarious.

Last year, a photo of me began circulating with a beard. Apparently, I am now the face of Lumbersexuality. It started because my friend wanted to photograph me as a lumberjack and he sold it as stock photography so now the photo is just everywhere from Buzzfeed to The Atlantic.

So, Steve dressed up as a lumberjack with a big cylindrical speaker system that looked like a giant log. Basically, as a nod to me, poking fun of my unfortunate relation to the term Lumbersexual.

So what should we wear?

Everyone has their own preference. Wear whatever you want—just get creative with it. There are so many different things you can do. There was a girl one year that wore nude underwear and made “Censored” signs. That was awesome.

It doesn’t necessarily have to be underwear—you can come it in a onesie if you want. We’ve had people come out in a onesie with the butt flap open. We also have a lot of people who will wear underwear on top of tights or normal clothes.

It’s not about showing skin. It’s about being silly.

I like to say, “Let your Freak Flag Fly.” However you interpret that is cool with us, except…

No thongs. No pasties. It’s for The Children’s Tumor Foundation.


So, important question: Bloody Marys or Mimosas?

My girlfriend is allergic to oranges so I feel like I have to go with Bloody Marys here.

And, if you had to invite five people to run and brunch, who would they be?

1. My girlfriend, Jordan, because obviously.
2. Anthony Bourdain because of his knowledge of food, his ability to drink, and his raw humor.
3. Aziz Ansari
4. Jennifer Lawrence
5. Stephen Colbert

What do you say to people who have Valentine’s Day plans—who comes to Cupid’s Undie Run?
Everybody. Singles. Couples. It’s an opportunity to do something fun and totally different. It’s a holiday that some people absolutely love and some people absolutely loathe. Regardless of who you are—it’s a chance to have the most unique and most exciting Valentine’s Day weekend ever. It’s on the 13th this year so you can still go to dinner on the 14th.

Also if you’re single- here’s an opportunity to meet and hang out with 2,000 people—we’ve done half the work for you already.

The Bitches

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