Rajeev Gupta, 2014 Smallest Penis in Brooklyn Pageant winner, made out in Bill de Blasio’s front yard

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Rajeev Gupta, winner of the Smallest Penis in Brooklyn Pageant, resplendent in victory. Photo by Mary Dorn

In case you missed last week’s eeny-weenie contest at King’s County, rest assured that Brokelyn was there to capture the magic. But that’s not all we did: after watching 28-year-old winner Rajeev Gupta (aka ‘Rajkumar’) capture the hearts of audience members with his earnest, keep-it-in-his-pants show of manhood, we couldn’t resist getting in touch with him for an interview. We met up and talked about his audience-melting pageant answers, what he did with his prize money and how we wound up making out with someone in front of Gracie Mansion.

Okay, so you live on the Upper East Side. How did you even hear about this competition?

RAJEEV GUPTA: Well, I was just hanging out at a bar, chatting with one of the servers. It turned out he was a writer for Bushwick Daily and had just done a write-up of this competition. I love performing, I’ve done a lot of dancing and singing, and I’ve even done personality contests before. It seemed like a lot of fun.


What made you want to do it?

The $200 prize in cash sounded pretty nice. But also, they told us that we would drink for free all night. And that was amazing. The whole night, we were kings. 

Your answers at the pageant were pretty unique. Like, earnest and not woman-hating. What gives?

They asked us, “What do you like to do in the bed?” And I said what I actually feel, “making love.” And everyone thought that was cute. I understand women; they like to be treated with a lot of respect. The other guys were trying to use the competition as an excuse to whip their dicks out and be vulgar. Maybe they thought that that’s part of performing. But none of my answers had profanity. The girls there are college grads, you know? They probably got tons of that at frat houses.

Is it a bittersweet win, considering what the title of the contest was?

Actually, I think the title of the pageant is misleading. They never once asked us how long we were, they never measured. And in a flaccid state, they all look the same anyway. If the contest actually were about size…let’s just say, I would have lost.

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Raj looking down to see where he placed. Photo by Mary Dorn

How do you meet new people here, in general? Do you rely solely on zany genital competitions in order to meet women?

I prefer meeting in daylight, in places like [coffeeshops], without the influence of alcohol. And I may be an introvert, but I’m not shy. I actually meet a lot of people in New York on the subways: I’m usually just curious about what they’re reading, or listening to, or doing on their phones. Human beings are a complex species!

So, how many phone numbers did you get out of it?

Well, I have the date coming up with the two sisters, but before I could really talk to anyone the press people swarmed me. And then, the whole bar emptied out kind of quickly because somebody pooped his pants.

Wait, what?

Yeah, it happened last year, too. Right as the winner is being crowned, somebody poops their pants. I think it’s a fetish or something. Anyway, it started to smell so bad that people just left pretty quickly once the event was over. But I guess whoever it was is nice, since at least they waited until after I was crowned to do it.

So what are you going to do with the $200 cash prize?

Oh, I already spent it. I bought myself new running shoes. I like running.

Have you done anything else as crazy as this since you moved to New York? 

This girl I met, we made out in what was essentially Mayor de Blasio’s front yard. That was pretty great.

How did this happen exactly?

I had met this girl few days ago in Bryant Park one afternoon, just randomly while I was enjoying my vegan lunch from Maoz. Two days later while coming back late from work at midnight, I happened to pass by her building, I texted her if she was up. She replied.. “Yeah, no, why?” I said, “Open your window.” Her apartment was on the ground floor by the street, and there she was, with somewhat sleepy dreamy eyes, she was excited and perplexed. I looked in her eyes and said, “Come out,” after a little hesitation, she walked out. I held her hand, gave her a hug and we walked to the East River, which was only a block away.

As we reached the river, we saw this green grass, moonlight shining on the water of the East River and stars all around. There was nothing better to do than make out! It was one of the most romantic moments of my life in New York. After few minutes, she told me, “Just so you know, we are not far from the Mayor of this city at this moment.” We were not exactly on his lawn, because that’s a guarded fort I believe, but we were very close, we could see his mansion!

Did the pageant seem quintessentially “Brooklyn” for you? What do you think of us now?

Honestly, I think it would have been the same in Manhattan. There might be a smaller turnout. There’s certainly a perception that Brooklyn is more tolerant and quirky. But coming from India, we watch so much American television and cinema. The dream is always Manhattan. My first intro to the city was the show Friends, and when I got here it wasn’t even a real thing! Like, no one can afford that apartment. So, I am looking forward to spending more time in Brooklyn. 

What’s next for you? 

I’m a Fulbright scholar, so I have to leave the US for good in a month when my study expires. But before that, I’m going to go on a road trip from NY to LA. I have this plan to interview 30 families in 30 days across Middle America along the way. They host me overnight, and I talk to them. I want to show a human side to this country that’s more than just coastal.

Stay tuned in to Rajeev’s cross-country adventures and other East-Meets-West musings by following him at @rajeevcinema, or checking out his website at www.guptagoesgreek.com.