All my worst dates have ended with karaoke. Eight years apart, two surprise attacks, and the sobering realization that the only way out is through.
The first time, I was 19. It was one of my first dates ever, with a cool film school guy who gave me two options: a moody dive bar in Silver Lake or a lively karaoke spot downtown. I let him choose, having learned from all the dating “how-to” guides that it wasn’t desirable to be picky. I told him, however, that if we went to karaoke, it was purely to observe. Under no circumstances would I perform.
The issue isn’t social anxiety. Shyness isn’t sanctioned in my family, and I’m a Sagittarius. The problem is that I’m a slightly above-average singer, which is the worst possible level of talent for karaoke. You have two options: be aggressively decent or performatively bad. Neither appeals to me as a former almost-pop star.
Yes, you heard me.
At 17, I made my mom take me to audition for The X Factor in Los Angeles. With her as my Kris Jenner, I somehow advanced three rounds, each time shocked to discover I had beaten girls belting “THIS GIRL IS ON FIIIIIIIIIIRE” perfectly on-key.
It quickly became clear the producers were less interested in my vocal abilities than in my chaotic relationship with my momager. When I accidentally admitted I’d been fired from a toy store for giving out too many friends-and-family discounts, my mother scoffed: “Sorry, we have a lot of friends.”
What was decidedly NOT Kris Jenner about my mother was that she felt compelled to inform the third-round producers that there was no way in hell I would skip college to become a pop star. Rest assured, she was immediately fired. And that’s why Dua Lipa is where she is today.
So naturally, public singing is kind of a touchy subject for me. Unless I’m several cocktails deep with lifelong friends or absolute strangers, I’d rather not lay my soul bare.
Which is why coming out of the bathroom to find my date at the front of the restaurant, a microphone in each hand, made me want to evaporate into thin air.
“There she is!” he announced, waving me toward the front. The place erupted in applause, as if I’d arrived at the end of his crowd work. Then the first few bars of “Genie in a Bottle” hit, and I realized I was in a hostage situation.
There was only one logical way out of this. Make it everyone else’s problem.
I started whisper-singing like the greats before me, immediately recruiting strangers to cover any notes requiring actual range. By the time the song crescendoed, I had sandwiched myself between a spirited group of Korean tourists belting along. I thought we were all killing it. Until my date scornfully yelled, “My date hates me! She’s running away!” into the microphone.
The energy instantly shifted. I even heard a few boos. This was no longer a duet but a duel.
When we sat back down, I reminded my date that I’d warned him against making me sing. Without missing a beat, he grinned. “Don’t worry. I have two more songs. Solo.”
I drank the rest of my wine, suffering through his greatest hits as he seemed entirely unbothered by the fact that he had forever ruined “Genie in a Bottle” for me.
After the date, I learned that being picky was much better than public humiliation. And for seven glorious years, I managed to avoid surprise-karaoke. Until I met a man who made the first guy look like an amateur.
The first left turn was when he ordered a piña colada at 8 p.m. on a Thursday in the dead of winter. When I made a joke about it, he got defensive. Great... this was going to be a long one.
Slurping his frozen drink, he informed me that there were only two categories of hot girls: thin and thick. He briefly paused due to a brain freeze, then informed me that I fell into the latter category. I nearly spit out my martini. But he wasn’t finished with his unsolicited performance review. My eyebrows were a bit too strong. My jeans could benefit from a lower cut. And my deep voice was on the cusp of sexy and annoying. If only I could work on my vocal fry.
I took a generous sip of my martini, then repaid him with my own analysis, informing him that his energy toed the line between “is this a bit?” and “are you actually this psychotic?”
When the server approached with the bill, she admitted that she and the rest of the staff had been placing bets on how long we’d been dating. Her guess? Two years.
I snorted. Apparently, we had great chemistry. Maybe that’s what happens when you never want to see someone again.
After drinks, my date walked me home, and when we got to my doorstep, he asked to use my restroom. I obliged because I'm a good person and I didn't feel like I was in danger. He was my height.
I showed him to one bathroom and used the other myself.
When I returned to my living room, I found him standing in front of my TV with the instrumental version of Grover Washington Jr.’s “Just the Two of Us” cued up, ready to serenade me.
Before I could muster a response, he launched into a full song-and-dance routine. I stood there, agog, as he twirled around my apartment singing in a strained alto. When he finally finished, I applauded, hoping to signal the end of the evening.
Unfortunately, at some point during dinner, I’d made the fatal mistake of revealing one of my favorite songs was “I Will Survive.” So he queued it up, telling me that I owed him a performance in return.
Cornered, I performed a haphazard rendition of the ‘70s hit, complete with choreography designed to usher him out the door. But he didn’t get the hint. So I told him I had a curfew. In my own apartment. At 27.
When he asked to see me again, I thanked him for his thorough assessment of my entire personhood but told him I didn’t quite feel a spark.
The next morning, I awoke to a Venmo request for half the bill.
By brunch with the girls, I was basically Paul Revere, foaming at the mouth with breaking news.
Everyone knows a bad date makes for a great headline.
First dates are already an absurd social experiment. You’re meeting a complete stranger to determine whether you might someday merge lives or accidentally unleash your freak.
And when it’s bad, it can be so good. Unless you feel unsafe. Then obviously leave. Otherwise, you’ve suddenly gone from romantic interest to investigative journalist, documenting the madness in pursuit of a thrilling story.
A boring first date, on the other hand, is frankly a waste of time and calories.
I put my theory to the test on Instagram, asking my followers which was worse: a bad date or a boring one. Of the 103 people who voted, 62% agreed that a boring date was the bigger offense.
Within minutes, my DMs became a compilation of dating disasters I now refer to as Now That’s What I Call Trauma! People recounted dates from years ago in forensic detail. And as the submissions poured in, I found myself cackling at the modern courting tragedies.
So, courtesy of those who lived to tell the tale, I present the Hall of Famers.
The Art of a Bad First Date:
The Overplanner — There is such a thing as doing too much. Selecting a nice spot for drinks or a light activity is thoughtful, but picking someone up at noon with flowers, then subjecting them to a full day at LACMA, a forced photoshoot, and a five-course meal where the entire restaurant sings “Happy Birthday” borders on kidnapping. Keep it to two drinks, one location, and no flowers. A first date should never last longer than a 9-to-5.
The Method Actor — Sometimes bits are fun. They’re a product of good banter. But there’s a reason they’re called bits. They’re meant to end. One reader took a girl on a date to an escape room (which might be worse than karaoke, but I digress) and suggested they roleplay as members of Pablo Escobar’s crew. Somehow, his date interpreted this prompt as “woman with Southern accent” and committed wholeheartedly to the role. She refused to break character long after they’d escaped, carrying her Southern drawl through dinner despite his gentle suggestions that they return to reality. As a rule, method acting should be reserved for pretending you’re enjoying the date.
The Woo-Woo One — Listen, LA is full of basic astrology chicks. I proudly subscribe to that club. But it’s a little unusual when a man brings a girl back to his place and casually reveals that an entire wing of the house is sectioned off to preserve his late mother’s energy, right?
The Fraud — One reader went on a date with a man who claimed to be a 25-year-old doctor. As the evening progressed, his résumé began to unravel. Turns out he was a 30-year-old nurse who allegedly lied because “nobody respects nurses.” UM. Nurses save lives! Liars are lethal! At least he came clean. I once went on a date with a man who refused to tell me his age, instead offering to let me guess within a five-year range. When I guessed 33–38, he nodded along. The next day, my cousin discovered he was 42. Come on, people. It’s modern times. I can find your blood type with a first name and a mutual!
The Opportunist — Men should always pay for first dates. Sorry, I said it. It’s about the gesture, which is why the recipient of said gesture should keep it chill. This isn’t your excuse to run up a tab. One reader’s date insisted on a pre-dinner donut stop before ordering the most expensive cut of steak on the menu and housing three different desserts. Girl, did you come for a shot at love or to break your intermittent fast?
The Accidental Catfish — What happens when you show up to a date thinking you’re meeting someone else? That’s the problem with not saving numbers. One reader agreed to a date with a man she’d confused with another guy she was interested in. When she realized her mistake, she pulled off the performance of a lifetime. And what was she rewarded with? A man who lectured her for not wearing heels (to R&D Kitchen, pls) and told her she’d have trouble finding a husband if she didn’t cook three homemade meals a day. Lol. I hope he finds the superwoman who will serve him salmon in stilettos.
The Hothead — I’m partial to lovers not fighters, so I can only imagine what one reader felt when her date’s argument with the man in the neighboring booth escalated to the point where the other man took off his shirt, ready to fight. It’s just like... who wins in that situation? And where is security?
The Monologuer — We’ve all been there. I’m sure I’ve done it. Actually, I know I’ve done it. But then I remember conversations are a two-way street. One reader went on a date with a man who punctuated every sip of his drink with another tale about his career. She nodded along until he finally asked about her line of work. She told him it was a long story, but she’d share if he was interested. He said no. OK PERIOD, KING. NO IS A FULL SENTENCE! After dinner, she set off on foot, unaware that he was walking behind her while she gave her sister the tea. He overheard her less-than-glowing review, startled her with a “Hey!” then headed straight to his car, leaving her to walk home alone. Come on, if you’re going to monopolize someone’s evening, the least you can do is offer them a ride home. But only in silence.
The Trauma Dumper — There’s being emotionally available, and then there’s being held emotionally captive. One reader went on a date with a man who got so drunk he unloaded years of unresolved family trauma before collapsing into her arms, sobbing. She showed up expecting drinks and left with a crash course in psychotherapy. She works in finance.
The Two-Timer — If you’re living a double life, best not to choose a popular restaurant for your bad behavior. One reader was out with a man when an irritated woman approached their table to tell him that her friend (we’ll call her Sally) was trying to reach him. Flustered, he didn’t notice the woman discreetly slip my reader a note, which alleged that he’d declared his love for Sally, failed to disclose an STI, and ghosted her just days earlier. Horrified, my reader made him call the poor woman, then slipped away to join the girls at the neighboring table. Days later, my reader found out he’d told Sally he was only meeting up with an old fling to end things while also asking my reader out again. Is it time to reboot John Tucker Must Die?
Let these stories be entertainment, not cautionary tales. In a world so measured and algorithmic, there’s something refreshing about the spontaneity of human connection and its inevitable disasters.
There’s also great freedom once the possibility of romance dies. The pressure is gone. The fun can begin. So what if it doesn’t work out? Now you have another piece of amazing lore.
As we’re reminded in one of the greatest films of our generation, A Cinderella Story:
Even if the game ends in karaoke.
[A NOTE FROM THE AUTHOR]:
I once tried to escape a date midway through dinner at the Black Cat in Silver Lake by hiding in the bathroom, only to lose my nerve when the managers offered to sneak me out through the kitchen. Instead, I swallowed my pride and returned to the table.
He looked up at me. “Did you get my text?”
I checked my phone. It read: “All good in there? Or did you fall in?”
All I blurted was, “Baby, that’s just IBS,” before sprinting to my car.
your best piece yet! when are we getting a book!!!???
My only issue with your writing is that I can’t see your face. You have the talent of a writer and a face for Vogue. Thoughts and prayers during this difficult time.