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Bobby Gill is a co-founder of Cupid’s Undie Run, a charity organization raising money for Neurofibromatosis research. The half-naked, fully-fun race occurs in multiple cities across the country and world. Register for the run here. If you can’t make it to a race, don’t worry! Feel free to donate here. We highly suggest doing the run because underwear!

Brightest Young Things: What is Cupid’s Undie Run? Or as I nearly keep saying, Cupid’s Undie Runs.

Bobby Gill: Cupid’s Undie Run is a 1 1/2 mile underwear run in February. You’ve got 2,000 people out there running around in their underwear, having a good time. There’s a big party before and after the run. It’s this huge, ridiculous day where everyone is half-naked, and it’s all for charity.

BYT: Finally, being half-naked for charity. We’ve been waiting for this day. What is the charity and how did that come about?

BG: My friend’s little brother had this rare genetic disorder called Neurofibromatosis or NF for short. It causes tumors to grow on the nervous system and can result in deafness, blindness, paralysis, severe pain and all kinds of nasty stuff. We wanted to do something for him, a charity event that stood out. The idea of running around in our underwear and partying in our underwear seemed like a fun thing to do so we went for it. The first year we didn’t even have permits. We just kind of went out there and did it. It was a great time and we’ve been doing it ever since.

BYT: How many years have you been doing it?

BG: This will be our 7th year in D.C. We started here and that first year raised $10,000. Over the years it’s grown and this past year we raised $3.5 million alone and about $8 million since we’ve started. This February we’re hoping to bring in another $5 million.

BYT: What’s it like having a completely selfless, beautiful job while most of us are self-involved narcissists? It’s gotta feel nice.

BG: Of course raising money for charity with this dumb idea we had years ago…to see it turn into something successful that is actually fundraising money for NF research is fantastic. It’s wonderful to see the progress being made.

BYT: Speaking of progress, do you have access to information about the research? I’ve always wondered how that works for organizations whose function is raising money for research like this.

BG: It’s funny you ask that because when we started off we approached the Children’s Tumor Foundation who is the world’s leading organization that funds NF research. We approached them with our idea for an underwear run and all the money is going to go to you guys and they said “Ha ha ha, underwear and drinking and a children’s charity, you must be kidding.” They didn’t want to touch us with a 10 foot pole but they gladly accepted the money. Of course, over the years as we’ve grown, we’ve proven ourselves to be not just a bunch of wild, ridiculous party animals who are doing risqué endeavors on the streets. At this point we contribute to about a quarter of their research budget every year so we have a really good working relationship with them now. With that they’re able to do tons of really good research. There are all kinds of things being done now that weren’t possible in the past because of this greater funding now available.

BYT: That’s amazing. I assume you chose February because it’s more challenging to run in your underwear in the cold, but why Valentine’s Day? Did President’s Day Undie Run just not have the same ring to it? No one wanted to see someone (un)dressed as James A. Garfield?

BG: First off, they do. If we could have a President Taft Run, we would. When we came up with the idea of Cupid’s Undie Run it was conceptualized on January 3, 2010 in an email between 3 people. We looked at the calendar said okay, what’s the next holiday coming up. That next holiday was Martin Luther King, Jr.’s birthday and that did not seem appropriate. We looked at the next holiday after that which was Valentine’s Day. It was more a matter of timing but over the years we’ve adopted the message of Share the Love and Do Something for Others and of course Cupid is a chubby little baby in underwear so it was the perfect combination.

BYT: You’re on the cover of Runner’s World this month. How did you swing that?

photo courtesy of Runner's World magazine. #RWCoverSearch presented by Tag Heuer and Asics.

photo courtesy of Runner’s World magazine. #RWCoverSearch presented by Tag Heuer and Asics

BG: We wanted to be on the cover at some point so I did some Googling and learned there was a cover search contest going on. I proposed to my team, internally, a few of our race directors in different cities who I thought would be good candidates for stories we could tell in hopes of trying to get them onto the cover. I’m generally not one for self-promotion so I was looking for other people to take that spot. Everyone on my team insisted I tell my story, being one of the founders and I used to be an ultramarathon runner. The team felt that would be relevant, of course. We entered the competition. There were 1600 entries which were narrowed down to 100 then 10. They brought us to New York for a big photo shoot and then in late October they unveiled the winners live on the Today Show which was kind of cool. In the green room Martha Stewart randomly came up to me and was like “What are you doing here?” I went into hustle mode and tried to recruit Martha Stewart to run in her underwear for charity. She was not interested.

BYT: You didn’t want to ask Matt Lauer? I feel like Matt Lauer would 100% do it.

BG: I didn’t get a chance to ask Matt Lauer but Natalie Moralis, who was one of the judges for the cover search contest, said she was going to probably run in our NY Cupid’s Undie Run.

BYT: What’s it like being a model now?

BG: That cover shoot…I had 3 weeks’ notice for that. I was not prepared to do an underwear photo shoot. It crept up on me and suddenly they’re taking half-naked pictures of me for the cover of a magazine. I kind of wish I had a 6 pack on that cover.

BYT: Do you have any hot tips for race day?

BG: We don’t really have any rules. We don’t take ourselves too seriously. Get creative, although it is for a children’s charity so keep it PG-13 at the most.

BYT: What’s the most comfortable thing to run in? I would assume, for men, a nice boxer brief. You gotta have support.

BG: Race day is serious business. I go full-on briefs, tighty whities. It’s classic. They kind of keep everything together.

Take a look at last year’s Cupid’s Undie Run for what-to-wear inspiration. We’ll see you at the race!