Jimmy Fallon asked people to share their worst first dates, and some were just laughably bad
Romance doesn't always come easily, does it?

As the saying goes, "You have to kiss a few frogs..."
Dating has certainly evolved over the years—we’ve gone from courtship being purely a financial arrangement (not that this trend has ever truly died) to knights jousting for a lady’s favor, to casual hookups, to now, when romance is primarily found through an app more than anything else.
Technology used for meeting that special someone has become so advanced that you can base your search entirely upon specific interests. Like, oddly specific interests. Think a fellow cat person would be the purrfect match? There’s an app for that. Wish to “love long and prosper” with a fellow Trekkie? There’s an app for that too.
No matter the changes, one thing remains the same—dating is awkward. It’s got all the unspoken formalities of a job interview, disguised as innocent fun. The balance between playing it too cool and too eager is hard to find even for the smoothest among us, and usually results in total embarrassment. Even if we aren’t the ones committing those embarrassing acts ourselves, we are often the reluctant witness to them.
Terrible dates might not always be fun in the moment, but they can be just as important as the good ones. They can teach us a lot about ourselves and what qualities we want in a partner. And at the very least, they can teach us to embrace social clumsiness with a sense of humor.
Jimmy Fallon recently asked his Tonight Show audience on X (formerly Twitter) to share a “funny or embarrassing first date story” for his ever popular #Hashtags segment. The best part—some of these awful first dates ended in marriage. There’s hope for us all.
Below, find 15 stories that are truly the best of the worst. How do some of your first dates compare?
1. "After a nice dinner, she invited me to her house. On the way up, inside the elevator, I decided to push the button to stop between floors and give her a kiss... She had a phobia of closed spaces and she smacked my face as a reflex, two punches after we were kissing and laughing.” – @PanqueAlgarvio
2. “His jeans were so tight he couldn’t sit down. Stood at a bar stool the whole time.” – @onlyintheozarks
3. “Waiting 4 my date when an older couple asked me for a ride. my date came up and said sure! We drove them home & they asked us to come in. Date said “sure”. I pulled him back & asked why he wanted to hang w/strangers. He said ‘sh@t! YOU DON'T KNOW THEM!?’ We bolted!” – @natashaham75
4. “Before the date, we had been chatting about books we liked and I talked about a great book I just read. We went on the date. I loaned her the book. She ghosted me.” – @thenextbarstool
5. “The worst first date I ever had was when my date locked his keys in the car and I had a curfew so he had to break his car window out to get me home on time. Didn’t think I’d ever see him again but we wound up married.” – @csleblan
6. “First date movie ‘Basic Instinct’ not realizing how suggestive it was. We just thought it was a mystery thriller! We left the movie discussing how each character could have actually murdered someone. We're married now.” – @Southrnbell_Amy
7. “First date with my ex husband was a double date with his parents. The preview for ‘Speed Racer’ came on, and she leaned over me to say to her son, ‘You know what your dad's nickname in the bedroom is?’" – @theostoria
8. “A friend asked me on a double date as a blind date with his date's friend. I went to the bathroom and came back just in time to hear my date say to her friend, ‘why do I get the ugly one?’ I said good night to all three and headed home, leaving her w/the bill.” – @StevenTrustum
9. “He loved cheese. I was subjected to a 2 hour conversation/lecture about cheese, and why cottage cheese is not cheese!” – @Optimist_Eeyore
10. “He took me to an Asian fish market. We walked around looking at live & dead fish for a while. I don’t like seeing dead animals & I don’t eat seafood. Then we sat on a curb & he pulled out a ziplock bag of pineapple for us to share. I don’t like pineapple.” – @markayhali
11. “My cousin set up a first date for me with a family friend. During a break from dinner, Mr. Man follows me into the ladies’ room, comes up close and says in a low voice, ‘I shave my butt.’ Can’t remember what I said in response but the evening ended abruptly.” – @carli_zarzana
12. “I once took out my high school crush to a sports bar and ordered the spiciest wings there in an attempt to impress her. Not only was she not impressed. The next morning I woke up with heartburn.” –@Dmonster38
13. “My date showed up with his bestie and girlfriend, and they talked through dinner about people I don’t know. Walking to the car, he gave me a wedgie because he thought he hadn’t been paying enough attention to me.” – @surrealDazey
14. “I was taking my date home and was pulled over by the police for speeding. When the cop came to my car, she jumped out and told him she had to get home. She walked home and I never heard from her again. I'm not sure who's #WorstFirstDate it was mine or hers!” – @eastriverbear
15. “After an evening of dancing with a first date, leaving the dance hall, I had to take a quick pee break. Rushing out to the parking lot, I see a lady, I grab her and swoop her around, and plant a big wet kiss on the lips. She was another guy's wife. Oops!” – @seadogskamore
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Mom is totally humiliated after her kindergartner tells the teacher what she does for work
She was clearly mortified.
A mom is embarrassed by her child.
One of the great joys and stresses of parenting is that you never know what will come out of your child’s mouth. When you have young, inquisitive kids, they can say really inappropriate things to people without realizing they were being rude or possibly offensive. TikTok influencer Aurora McCausland (@auroramccausland), known for her DIY cleaning tips, recently told a funny story on the platform about how her son believes she makes a living. The problem was that she heard about it from her child's teacher.
Mom is embarrassed by her child
“The other day, I went and picked my five year old up from school and when I get to his classroom his teacher pulls me inside and says, ‘Hey, today he wanted to tell us about what Mommy does for work and said that Mommy makes videos in her bedroom but only when I'm [he’s] not at home,” McCausland recalled.
Given her body language while telling the story, McCausland was clearly mortified after hearing what her child said to his teacher. It makes it look like she may be posting videos to adult sites while her child is at school, which most people wouldn’t want their son’s teacher to know about.
The good news is that another teacher was there to clarify the young boy's comments by adding, “I think she makes TikTok videos.” The uncomfortable situation was a great invitation to chat with her son about what she does for a living. “So I have to have a conversation with my son about how he tells people what I do for work,” she finished her video.
The funny video went viral, earning over 1.7 million views on TikTok, and inspired many people to share the times when their children had funny ways of explaining their careers. The commenters were a great reminder to parents everywhere that if your child says something embarrassing, it's ok, just about everyone has been through it.
Moms share their most embarrassing moments
A lot of parents spoke up in the comments to show McCausland that she's not the only one to feel embarrassed in front of her child's teacher.
"My son told everyone that we were homeless (because we don’t own our home, we rent)," KBR wrote.
"I work in ortho.. my daughter told her teacher I steal people's knees bc she heard me talking to my husband about a knee replacement," Aingeal wrote.
"My son told a teacher we were living in our car over the summer. Camping. We went camping," Kera wrote.
"In kinder, my son thought Red Bull was alcohol and told his teacher I liked to have beer on the way to school," Ashley wrote.
My niece told her teacher her mom and dad work at the wh*re house. They work at the courthouse," Ellis wrote.
"My husband works as a table games dealer at a casino. Kindergartener, 'Daddy's a Dealer!' We now start every school year clearly stating he works at the casino," CMAC
"My son said we lived in a crack house…There’s a tiny chip in the wall from the doorknob," KNWerner wrote.
"My dad is a hospice chaplain and officiates a lot of funerals. My son and nephew were asked by their preschool teacher if their papa was retired or had a job. They told her his job was to kill people," Tiffyd wrote.
"My son said "my dad left me and I'm all alone" to a random person at the zoo. My husband was just at work," Shelby.
"I am now in my 70s. In my gradeschool, during the McCarthy era, I told my teacher my dad was a communist. He was an economist," Crackerbelly wrote.
"In Kindergarten, my daughter told her teacher that mommy drinks and drives all the time. Coffee. From Starbucks," Jessica wrote.
"Well I once told my kindergarden teacher a man climbs over our fence to visit my mom when her husband is not home... It was a handy man who came to fix gates when they were stuck," Annie wrote.
Ultimately, McCausland’s story is a fun reminder of how children see things through their own unique lens and, with total innocence, can say some of the funniest things. It’s also a great warning to parents everywhere: if you aren’t clear with your kids about what you do for a living, you may be setting yourself up for a very embarrassing misunderstanding. So, even if you think they know what you do ask them as see what they say, you could save yourself from a lot of embarrassment.
This article originally appeared last year and has been updated.