Six comedians spill their guts and tell us about the romantic failures they won’t forget. Dare to share yours?
As told to Dorian Geiger
“Love is rich with both honey and venom,” goes the Latin proverb.
For the various comedians we spoke to this Valentine’s Day about the romantic failures they won’t forget, this was often the case.
These are some of the most entertaining, poignant, endearing and awkward stories of failed love from America’s funniest people, which goes to show: happily never after isn’t always a bad thing.
Casey Wilson: He was a man amongst men
I’ve had so many spectacularly bad Valentine’s Days but this one stands out.
I was a high school senior in Alexandria, Virginia. I was in DC at Christmas time and I met this guy. A kid. I was a junior in high school, and he was a freshman, in ninth grade.
You don’t often see an “older gal” romancing a freshman. I thought he was like wildly charming, a man amongst men. We started dating – casually – because I lived in Virginia and he lived in DC.
I came to find out he was the heir to a toy company fortune. I was very titillated and intrigued by that.
We’d gone out on two dates and I may or may not have taken his virginity. At the time, I felt very much like it was Romeo and Juliet, like we lived in two different worlds. I went to this public school from that movie Remember the Titans and he went to this very fancy private school in DC. I felt very like we were being kept apart by class structure.
On Valentine’s Day I put my foot down: “You’re coming to Alexandria.” Of course, he had to ride the metro because he was too young to drive.
I decided that we would go to TGI Fridays with another couple. I’m waiting and waiting for him; he was supposed to call me when he got to the metro. I never get a phone call. Now my friends are over, they’re in my living room, they’re very drunk, talking to my parents, and I get this phone call. I think it’s him. It was his mom.
“I want you to stay away from my son. He’s not taking any metro to see you. He won’t be seeing you again – ever.”
His mom broke up with me. I think she got wind of the fact that we had slept together and freaked out.
Look – as a mother of two young sons now, I don’t blame her. Looking back, I was way too aggressive. I wouldn’t want any of my kids dating me. Nuh-uh. Of course, I’m still hanging onto a little anger, but I’m going to try to let it all go because now I empathize with her. I’m in her shoes now – minus the humungous fortune.
Casey Wilson is a writer, actress and comedian who starred in the ABC series Happy Endings and NBC sitcom Marry Me. She is a former cast member of Saturday Night Live. Her film credits include Gone Girl.
Erin Gibson: I got stood up for Katy Perry
I was working as a writer-director at Funny or Die and I had done a video with a celebrity who contacted me a couple weeks later and said, “I want to set you up with a friend of mine.”
His friend is Josh Groban. I don’t date celebrities. I am not on that level, so I was flattered that person thought I could move up the rungs.
So me and Josh are texting, and I suggest we get dinner the next day, which is Friday. And he’s like, “Oh, I think I’m coming down with something.” I thought that made sense since he’s a singer, he’s probably really sensitive about his voice.
On Friday, I go to Sarah Silverman’s birthday party with my ex-husband, who I am still friends with – that’s another story – and he has to leave to go to another party. I’m there alone when I meet this handsome guy. Me and handsome guy talk for four continuous hours.
We were sitting on a pool chair and I had this dumb app on my phone that lets you look at the stars, and it tells you what constellations are what, and we’re doing that, and we’re there so long my one friend there kept coming up and going, “Are you guys on acid? I don’t understand. Why are you sitting here for so long?”
And I’m thinking, “We like each other, dummy.”
The party ends, we get in the elevator and guess who is also leaving the party? Josh Groban and he’s with Katy Perry. He didn’t see me or recognize me. He did me the biggest favor standing me up for Katy Perry because handsome guy is now my husband.
Bryan Safi: I lied about shaving my chest hair
It wasn’t until my senior year of college at NYU that I had come to terms with my sexuality.
I bought a poster of my favorite movie from childhood – Big Business – and put it on my dorm room wall. I threw a comforter on my bed purchased on a trip to Dollywood for my 21st birthday when I was still “straight” – a quilted image of Dolly’s enormous head and hair, an eagle swooping in on her, with the quote, “Oh Bless her Lord, she’s an eagle when she flies.”
And with that, I was ready to date men.
He asked me to come visit him for the weekend and stay overnight. This was something I’d never done. Up to this point, we had only kissed. It shot me up with confidence and then right after, gave me shot of self-doubt. Have you ever noticed that whenever anyone has a crush on you, all you think about is what’s wrong with you?
For me, it often comes down to my chest hair. I had plenty of it, so I decided to shave it off.
When I arrived in Connecticut we got dinner, got a little drunk, got into bed, got going.
“What’s going on with your chest? Did you shave it?”
“It’s really spikey.”
“It’s always been spikey. It’s kind of a sensitive subject.” Lie.
When I got back to New York, things were weird. I hadn’t heard from him in a few days but finally he called and said, “Hey. We need to talk. My throat really hurts. Any idea why?”
“Because you’re sick?”
“Or because you gave me an STD?”
“I think maybe you’re just sick.”
“I think maybe you’re just a liar.”
I was humiliated. How could he call me a liar?!
“I’m not a liar!”
“What about your chest hair?”
I hung up. I was a liar. And it wasn’t an STD. I found out months later that he really was just sick.
Sandy Chansamone: Dating on Tinder … back in the day
I met my boyfriend on Tinder. So you know it’s going to last…
We’re going on three years now.
Whenever people ask me how we started a conversation, I confidently say I’m pretty sure he said something super funny. Months later, I logged into my Tinder account to reminisce about how it all started. It turns out his first words to me were, “Hi Sandy :)” I guess my memory isn’t as good as I thought.
He’s very sweet, wears all black and is all tatted up. He’s a kind soul and we ugly cry at least once every episode of Game of Thrones because there is always a reason to ugly cry watching Game of Thrones. If a dragon is ever at risk of being harmed, our eyes well up immediately. We share the same passion for all you can eat Korean BBQ, and work well as a team.
The one downside to finding someone online, particularly Tinder, is that it is very limited in the information you get. I don’t know what Tinder is like now, but back in my day, Tinder just gave you a first name, age, a few pictures and a short blurb about them.
By the third date it dawned on me: I don’t know his last name.
He told me it’s Landey.
If this works out, I’m going to be Sandy Landey. Sometimes life plays cruel jokes on you.
Molly Kiernan: The best friend that got away
I’m recovered from an eating disorder. My anorexia, bulimia and binge-eating disorder took over my early 20s. It was hard to keep a job, hard to maintain relationships, and hard to even get out of bed most days. Finding comedy was one of the most important parts of my recovery: it gave me something to be passionate about.
My illness really affected all of my relationships, and the one I still haven’t recovered from is a friendship I had in college. Let’s call this person Todd.
I met Todd the first day of my freshman year of college, and we immediately hit it off. We were both a little out of place at this big sports school in the midwest and preferred to spend Saturdays listening to music instead of going to football games. Whenever we went, we’d stand next to each other and pretend to know what was happening.
We were one of those pairings that spent so much time together, everyone assumed we were dating or asked why we weren’t. I really cared about him but wasn’t ready to admit to myself that I liked him as more than a friend. I wasn’t ready to really fall in love.
Todd helped me through some really dark and depressing times, but I made a mistake that hurt our relationship. I didn’t open up to him. I didn’t tell him how much I needed him, how great I thought he was or how we should’ve dated.
Some of this was not my fault. My disorder left me unable to really feel emotions. It wasn’t until I had already graduated from school and went through about a year of intense therapy and nutritional treatment that I started to feel again.
That’s when I sent Todd this incredibly embarrassing email. I spilled my guts about how I thought we were meant to be together, even though I hadn’t talked to him in so long.
When all of your emotions come flooding back at once, you feel them big and hard. It’s emotion-vomit. They get all over the place and come out in weird ways: like a long email sent from a treatment center in Boston to your friend who was now living an entirely new life in California.
Todd responded very nicely but he had moved on. No shit. I was sad, but I understood. I don’t think about Todd romantically anymore. But I think about how our friendship has never recovered. He visits New York sometimes, but I’m never the first one he calls.
I wouldn’t want to date him now, but I miss my old best friend, and in that sense, he’s “the one that got away.”
Molly Kiernan is a comedy writer and performer and can be regularly seen performing at the Magnet Theater in NYC. She is the creator, host, and producer of Molly’s Guilt Free Comedy and Ice Cream Social, a variety show about self-love and celebration.
Neal Medlyn: In junior high I gave my date a $300 “mum” of flowers with a teddy bear in the middle. She was mortified
I grew up in a tiny town in East Texas which has a tradition of homecoming mums. Homecoming is a football game and after it is the homecoming dance. Traditionally you invite someone to be your date, kind of like prom but open to all comers.
The homecoming mums were gifts you’d give your date: elaborate flowers with ribbons and football-themed gewgaws hanging all over them in your school’s colors.
When I was in junior high, after going through a phase of rabidly collecting comic books, my allowance money started to pile up since I rarely left my bedroom where I spent most of my time writing house music on my keyboard. I asked my friend Michelle to be my date. It seemed obvious it was just as friends, but I think I hoped it would be more than that once she saw my moves on the dance floor.
To that end, and because I was flush with cash, I went to the florist and bought the most expensive, insane, elaborate mum of all time. I think it cost almost $300. It was, like, five feet long. It had a teddy bear in the center of the flower. I seem to remember it lit up. It was crazy.
The day of homecoming, I gave it to Michelle, who was mortified. She wore it for a few minutes, I think to humor me, but then took it off because, like I said, it was an insane thing to give someone. It was the first of many times in my life that I did or gave someone something that was wildly out of scale and ended up being embarrassing for everyone involved.