18 Funny First Date Stories That Will Make You Laugh Out Loud

Written by Natasha Funderburk

Have you ever been on a date that spelled (or maybe even smelled) disaster from the start? These 18 funny first date stories are guaranteed to make you laugh out loud, and be thankful that your worst date didn’t end in quite the same amount of despair. And if it did, then girl… you gotta give us the details!

Funny First Date Stories

“Being a single mom I didn’t have a lot of time to date or meet people, so I dated/talked to men on the internet. One guy was really nice, talked about how he owned a construction company, and seemed like an all-around amazing man. We were going to meet for supper. He claimed his truck broke down. Okay, no big deal. I went and picked him up. We had supper, but it turned out he “left his wallet at home.” Okay. Not a big deal – I could pay for dinner. We had a great conversation, great meal, the date really went well. When I went to drop him off at his “home,” – yeah… he was homeless and wanted to know if he could stay the night. No thank you!”

“I dated a guy for three months who was very nice. We went on weekend getaways and he would pay for everything. Then, one day, he finally told me his last name. He was in a motorcycle gang and had been released from prison recently for attempted murder and drug charges. I never talked to him again.”

“My sister had a friend that had a great date, until the goodnight kiss. They were kissing and his front tooth fell out in her mouth. She handed it back to him, and he ran to his car and never called her.”

“I met a man at Granite City for a date and he had adult ADHD so severe that he had to walk briskly around the inner table area every 2-3 minutes to help calm himself down.”

“My current husband; we met online and when we met we couldn’t put our fingers on where we knew each other from. Turns out, I dated and lived with his best friend pre-kids, and we all used to hang out together. So basically, I dated my husband’s best friend.”

“I met a guy at Starbucks once who lived in his car with his 10 cats. When I walked over to his car, the smell almost made me pass out. He stated he cleaned the litter box often. The litter boxes were kept in his car.”

“I went out on a date with a semi driver who asked if I wanted to drive down to Florida with him for a job, but he had to pick up his wife in Florida and bring her back home. I left very quickly.”

“I talked to a guy on the internet for a good two months. He proposed to me before meeting, and wanted me to sell my house to move in with him. He was pretty persistent, as in 50+ text messages a day, 30 phone calls a day. I ended up blocking him.”

“I once went on a date with a guy who was a Dooms Day preparer. He made powdered food, and he showed me his fall-out shelter. He was very proud of his 120 year supply of powdered milk (he was a big milk drinker and didn’t want to enter into the end of the world without milk).”

“I got my period while wearing a white dress in his car on the way to a concert on New Years.” (Spoiler alert: they’re now married!)

“It wasn’t our first date, but one of our first five dates. My current husband wanted to impress me with his fire-making skills at his house. Our date was sitting around his fire pit, eating pizza and talking. He had a real pine needle/fur Christmas wreath that he was suppose to put on his Grandparents grave a year ago, but he never did. So he decided to use that as kindling to start the fire along with his gas. So this year-old, dried-up Christmas wreath and a Mason jar full of gas was mixed together and lit. It was the biggest fire ball I have ever seen. He caught his tree on fire and about set his brand new truck on fire. Needless to say, I now start all the fires. He lost his man card when it comes to fire starting.”

“I went on a date with a dude I worked with, who I had been wanting for months to go out with. I showed up to meet him at a bar to throw darts and he was so hammered. Within a half an hour of me being there, his girlfriend used the “find my phone” feature and showed up looking for him wondering why he hadn’t come home that night.”

“On week 3 of dating my S.O, we had very organic-like date at home in the middle of June. Outside, in our secluded backyard drinking red wine, bottle after bottle in our gazebo, listening to all of our favorite music and dancing – yes, naked. Euphoric and in love to say the least. We drank well into the early morning until he probably had to carry me to bed. As odd as it sounds with being the on only the 3rd date, we spent our prior days together daily. This was just an extra special night.

The next morning I had woken up with the most excruciating red wine (axe in the forehead headache ), and a rumbling bloated belly. Only to notice HE WAS NOT IN BED. I frantically texted him, “where have you gone?” Scared that I might have done something dumb I didn’t remember the night before.
He responded that he was using the only bathroom in the house. 😳😬😰.
I was panicking since I yet have to even let out any fart or a burp the while we were ever together. I quickly responded that I needed to get in there soon, and if he could please hurry just a bit.

My stomach turned from a rumble to a hot soup that was about to fly out my ass! Holding it as much as I could (which is harder after 2 kids lmao), I texted him once more to “Please hurry!” He responded with three little letters: LOL, and that just made me want to bang the bathroom door down.

I couldn’t wait any longer, so I searched to my left, then my right. Right was the window and I seriously considered it but the future flashed of my shit running down the siding! The left was a clean waste basket. My ass couldn’t hold it any more. I frantically ran over and sat my ass over the poor trash and let it all go! It was the worst sound yet the best feeling of relief I’ve ever experienced!

It was all over. As I perked up and realized how mortified I was that the trash looked like a bloody massacre from a mix of cabernet and pino noir, there he was, standing in the doorway laughing hysterically at me! Needless to say that moment will never be forgotten about. We now are in the process of adding a 2nd bathroom!”

“One guy I dated explained to me how he was sleeping with two women who turned out to be neighbors. So he sent the first one flowers to apologize and she returned them. When I made a look of concern he said, “Oh don’t worry. The florist refunded my money.” Ummm, yeah buddy. Your money was what concerned me about that story.”

“I got a wasp stuck in my dress on a date one and literally had to strip naked in the bathroom.”

“I was stalked on an online dating app the 1st year I moved out of state. He was charged with two felonies and a misdemeanor.”

“I had a dude ask me if my boobs were real or fake. Another date, a guy asked me to his house for dinner. All was well until I noticed his toenail clippings on the coffee table.”

“I went out with a guy that told me all this drama about his ex, and also told me how he was a recovering alcoholic and drug user. As he’s telling me this, he proceeded to light a bowl and smoke in front of me. Like, okay, cool homie – you do you, but at least ask if I’m comfortable with it! Lol it was so uncomfortable and I got the heck outta there real quick.”