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My Greatest Regret Is Not Making Out with a 500-Pound Woman on a Shitty Talk Show

My biggest regret, the one that haunts me to this day, the one I think about more than any other, the one that sends me into cold sweats is, “What if I had agreed to appear on that sleazy talk show pretending I dated a 45-year-old 500-pound woman back...
May 26, 2013, 2:00pm

Illustration via Flickr user Christian Paparcuri

I’m writing this on my 33rd birthday. I’m sitting on my patio out in Greenpoint, Brooklyn, enjoying the quiet and fresh air. I’ve exceeded the expectations people had for me as an unconfident runt who grew up in North Jersey as well as the expectations I had for myself. I get to do comedy for a living. I have a beautiful girlfriend who is kind to me. My collaborators, my friends, and my community support me. I feel good. My life is good. I haven’t always felt like that, and I’m grateful that I can take the time to remind myself of it.


Yet on this birthday, I am sitting around thinking about regrets. Maybe it’s because birthdays are a time for self-reflection, and I’m the type of person who looks for any opportunity to ponder life. Probably it has to do with the fact that I had a dream when I was a freshman in college that I would only live to be 36, so a small part of me views this as the tail end of things since I’m neurotic and can’t forget a death dream. (It was very weird. I was lost in a forest, panicking, when a being of pure light who emanated serenity stopped me in my path and said, “Don’t worry, you’re halfway there.” I immediately realized that he wasn’t talking about being halfway out of the forest, he was talking about being halfway through my time on earth. I then realized that he was me post-death and was letting me know things ended peacefully. I woke up screaming, severely disturbing my roommate, a man known far and wide as the Russian Bear. Anyway, hearing about other peoples’ dreams is the fucking worst.)

As a largely unsuccessful comedian, I’ve become someone that younger people sometimes find and ask for advice, which I’m happy to give, even though it makes me feel old. I find myself dropping the same pearls of wisdom over and over: “Don’t feel shame about taking antidepressants, it’s an outdated stigma.” “Seriously, please don’t kill yourself.” “No credit is worse than bad credit.” “Leaving pee on a toilet seat is the worst thing you can do to your fellow man.”


But most of all, I tell people that they have to avoid living with regrets. They’ll eat you up inside. I know they eat me up. “What if?” is just about the worst question I can ask myself, and I want to avoid it at all costs for the rest of my life. And I have some huge what ifs that still bug me:

“What if I’d kissed Shelli on the banks of the D&R canal?”

“What if I’d stayed in Los Angeles in 2004?”

“What if I’d followed my gut and dropped out of Rutgers after my sophomore year?”

But my biggest regret, the one that haunts me to this day, the one I think about more than any other, the one that sends me into cold sweats is, “What if I had agreed to appear on that sleazy talk show pretending I dated a 45-year-old 500-pound woman back in 2001?”

Some background: I started performing at the Upright Citizens Brigade Theater when I was 20 years old. There were a lot of other manic, creative people there who were uncertain what they wanted to go for, let alone how to go for it, and it felt like home. It changed my life. Starting out so young was great—I was too dumb to be intimidated by the people around me. When I was 21 I was on a team with Rob Corddry and Jack McBrayer and I was sharing the stage with people like Rob Riggle, Rob Huebel, and Paul Scheer on a semi-regular basis. It was the most challenging, exciting shit in the world. I immersed myself in it and just tried to keep up.

Back then, I was known as a promising young comedian. People wanted to do stuff with me. I had a run in with a shady manager at one point who sent me out on a hand modeling audition without telling me that’s what it was, despite the fact that I have a skeletal deformity that gives me claw-like hands. I would occasionally get asked to be in other comedian’s videos, or to do shows with people I respected. It was a good time.


One thing you should know about me is that I have always looked very young for my age. Only now am I starting to look age-appropriate. For example, here’s me at 13, looking about nine:

That baby fat would stick around well into my high school years. I didn’t hit puberty until my junior year, and the process wouldn’t complete itself until I was in college.

So when I was 21, I was fresh-faced and tiny. My first paid acting gig was playing teenagers in sketches on Late Night with Conan O’Brien. Casting me meant they wouldn’t have to pay child labor wages.

I still don’t know who tipped off the booker of that sleazy talk show about me. I was still living with my parents at this time, and early one morning their phone rang. My mom came downstairs, excited.

“It’s a producer,” she said. “Fun!”

Now, in my memory, the show this person worked for was Rolanda, starring Rolanda Watts. But a quick google search tells me that that show ceased production in 1997, meaning it couldn’t have been hers. In any case, this producer was from the type of talk show that got popular in 90s—the ones hosted by wannabe Jerry Springers where KKK members would fistfight Black Panthers, or GG Allin would be a panelist talking about how getting raped by him would make a teenage girl’s life.

“We’re working on a piece here and we thought you’d be great for it,” the producer of the undefined show said.

“OK,” I said, already sensing a bizarre situation.


“We want you to come on our show and claim you date a 500-pound black woman. We’ve already got the 500-pound black woman.”

“Wait,” I said. “This is a talk show, right?”


“So aren’t the things supposed to be real?”

She burst out laughing.“Oh, almost none of it’s real. At best, people are lying and don’t think we know. We always know. We make most of it up.”

“OK,” I said. “Sorry, I’m a little confused. Can you explain this whole thing to me again?”

“Basically, you’re a scrawny white kid,” she said. “I hope that’s not insulting. It’s just true. And we have this 500-pound black woman. And we want you two to say that you date.”


“So the whole crowd can yell at you,” she said. “The 500-pound black woman is also 45 years old. We want people to tell her she’s ruining your life and stuff like that.”

“Wow,” I said.

“I know, right?” she said, her excitement mounting. “I don’t know if you’d be into this, but we were hoping you would make out with the 500-pound black woman in front of the crowd. That will really drive them nuts.”

“I have to think about this,” I said. “When do you need to know by?”

“An hour or so would be great.”

“Can you call me back then?”

“Sure,” she said. “I really hope you can do it! We can pay you three hundred dollars.”

I hung up and trudged upstairs to my kitchen, where my mom sat at our table, excitement washing over her face.

“Is it something good?” she asked.


“A talk show wants me to make out with a 500-hundred pound black woman,” I told her.


“A talk show wants me to—”

“I heard you,” she said. “That’s not acting. That’s not what you’re trying to do.”

“I know that,” I told her. “I’m not sure if I should do it.”

“Why would you?” my mother asked.

“Because it’s a chance to be on TV,” I said. “Maybe it will be good for a reel? And it would be kind of amazing to have footage of myself getting booed by a talk show crowd.”

“I don’t know, Christopher,” she said.

“I mean, like in a pro wrestling way, that would be really fun.”

We sat there, my mom sipping her tea, me staring at the ground. I ran over all the possibilities in my head. It would be hilarious to tell my friends to watch. But I’d only been on television once or twice before. What if this got in the way of the rest of my career? What if this was the last thing I ever did on TV? That would be a bad legacy to leave.

And worst of all was the emotional side of it. I’d watched enough talk shows to see what they were going for. People were going to yell at me and tell me I was crazy. But worst of all, they were going to mock this poor woman for her size, her age, and, knowing the intelligence level of these shows, probably for her race. It would be pre-supposed that it would be insane to love this woman.

It felt hurtful. I tossed the idea around in my head —she was a grown woman, able to make her own decisions. Maybe she was the most confident person in the world and would find the situation as funny as I would. But maybe she really needed that $300. Or maybe her self-esteem was so low that she was ready to wander up there knowing she was a lamb being led to slaughter.


Then there was my mental state—at the time, I was pretty consistently depressed and full of self-doubt. And I had social advantages. I was male and Caucasian, the things that are easier to be. This woman had to put up with enough already. If she was going to head up there, I didn’t have to be a part of it.

“That poor woman,” my mother said.

“I was just thinking the same thing.”

The producer called back a little later. I told her I couldn’t be a part of it.

“Oh no!” she said. “How come?”

“It just feels far away from what I do,” I said. “It makes me nervous.”

“I get it,” she said. “Maybe next time.”

I hung up, and I regretted it immediately. I still regret it today. What a dumb fucking choice. If I had footage of myself screaming at an unruly crowd who was mad I was making out with a beautiful big-boned woman, I could die happy. What an over-thought, over-sensitive, regrettable, piece-of-shit decision. Not a day has gone by when I haven’t wished I was less of a sad-sack melodramatic turd.

I could have been on a skeezy exploitative talk show making out and yelling at white trash audience members. I could have had my heel turn. I could have spent a glorious afternoon telling dirtbags with opinions to fuck off and let me live my life. I would have been lying through my teeth. I would have been good at it. And I would have had video of the whole thing.

I’ll go to my grave knowing I missed one of the greatest opportunities ever offered to me. Don’t make the same mistake I did. Take your chances, go into the unknown, don’t think too hard about the dumb shit life brings to the table sometimes. Make out with your metaphorical 500-pound black woman and leave regrets behind.


Previously by Chris: The Strongest Dwarf in New Jersey