For new relationships, dates can be hit or miss; especially first dates. Some are bland with the conversation drying up within minutes while others can be an absolute joy and lead to much more. The stories below from Void readers, however, are those rare instances in which something happens on the date that, regardless if you spend the rest of your life with that person, you’ll remember “this” date for many years to come. They are funny, embarrassing and everything in between.


  • It was my first time meeting his parents, and we went out sailing. The boom of the mast broke and sling-shotted my boyfriend off the boat. When he got back on we tried bungee tying the sail. While I was helping out with that, his dad let go of the bungee and hit hit me right in the mouth! I started bleeding and my lip swelled up. His dad felt awful but it kinda lightened the mood! – 18-24 year-old female
  • The first date, I showed at our pre-determined time of 8 p.m. I had an old car that started sometimes, so instead of taking that chance I left it running in her driveway. When she was finally ready 30 minutes later we went outside and my car was burning oil and the whole neighbor was a big cloud of blue gray fumes coming out of my car. – 36-44 year-old male
  • When I was about 14, I went to my boyfriend’s house and we rode bikes out to this meadow to have a picnic. He brought out seltzer water and said that we should pretend that it was alcohol, and kept calling it “bubbly” in an attempt to seduce me. Even at 14, I was embarrassed to be on that date. – 25-29 year-old female
  • High school prom after only dating my husband for four months. First time drinking, got so wasted he gave me a bath and I sh*t in the tub. He still married me though! – 30-35 year-old female
  • In high school, I took this younger girl to a party. I had one beer after being stuffed from dinner. I went to drive her home and for some reason the beer didn’t settle well in my stomach. While I was driving, I suddenly had to throw up. I tried to hold it in, but I threw up and it squirted out of the sides on my mouth. Some of it got on her and it was one of the most embarrassing moments of my life. – 25-29 year-old male
  • First date. After dinner we went back to my place and I fell face first down about 12 steps…all the way to the bottom. He came running down and laid down beside me and very sweetly asked, “What do I do?” I said, “Laugh, please laugh,” as I’m almost in tears and in a horrible position. Had to go to doc to check out my shoulder. Thankfully it was OK. And he still took me out again. – female (age withheld)
  • Talked to a guy long distance for a while then he flew to Jacksonville to meet me for a weekend. I pulled up to the arrival part of JAX and there he was, standing proudly in a Hawaiian shirt. Not your average Hawaiian shirt. It was the one with a red background and green palm trees that you can see from a mile away. Strike One. I said, “Oh, trying to get in the Florida spirit?” Thinking he was joking… he simply said, “No.” Strike Two. About 27 strikes later, on Sunday I surprised him with Jags tickets before he flew out that night. He was on his phone the entire game, so I dropped him off at the airport five hours before his flight. – female (age withheld)