I’m sitting here with my roommates and we’re a couple glasses of wine deep and getting an ab workout from laughing about our collection of hilarious stories from dating in the city this past year. We all go through the dating stage at some point in our lives. For us 4 though, its been happening unanimously in the recently rated ‘top dating city in the country‘ (you go Chi-town).. so the last 6 months have been pretty interesting to say the least. Here are some of our true life dating fails that are too good not to share..don’t know whether to laugh, cry, or become a nun:


“When I left the date he sent me a venmo request for half the meal”


Him: “Actually I get that a lot, and that I could be Adam Levine’s twin” (looked nothing like Adam Levine)


“Things went downhill when his top knot started looking better than mine.”


“I got food poisoning and threw up on him on our first date.”


“I panicked at the end of the date when he leaned in so I shook his hand.”


“When you go to check his Facebook for the first time 10 minutes before your first date and it says “in a relationship”


“It was kind of like a school project. 40 days with a 40 year old.”


(Had been dating for a couple months) Him: “I met a girl at the bar last night you would LOVE.”


“In bumble pic: Orlando Bloom. In person: Elijah Wood from Lord of the Rings”


Him: “I’ll be right back”        *never saw him again*


“It was going pretty well and the conversation was so good until he pulled out pictures of his boyfriend.”


“He wasn’t paying attention to me on the boat so I got on his jetski to get some fresh air – ran over a plastic bag in the water that got sucked into the motor and ruined the engine.”


“Told me he went on dates with two of the girls sitting at the table next to us”.


“He talked about himself during the entire first date. Then ‘all of me’ by John Legend started playing at the restaurant and he kept look up at the speakers and doing this weird winking thing.”


“I called him Dave the entire night. His name was Dayne.”


“I thought the candle in between us was fake and there was good music so I started dancing with it as a joke then lit my hair on fire.”

Here’s to knowing you’re not the only one with awkward failed attempts at love! Lesson learned: you can’t take things too personally, sometimes people are just really, really weird and awkward. And sometimes it’s you. And you know what.. these dating fails really make you appreciate the good ones so much more when you find them! You have to kiss some frogs first, ya know? Have your own that’s too good not to share? Join the convo in the comments below. There’s no such thing as bad dates, just golden stories.. xo liv

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Showing 13 comments
  • Nicole Y

    These are so funny! The dating phase is a love/hate phase lol!

  • Mallori

    These are SO funny. I once had a guy pick me up for the date. He asked if his shirt was okay, I was totally kidding and responded “no way, that’s a terrible shirt” (it was a solid color polo), he then grabbed another shirt from the backseat and changed his shirt!!!! To another solid color polo.

  • Keri

    Haha 😂 these are awesome. I feel like some of these could make it into a movie! My worst first date was with a guy who took me to play sand volleyball with his “couples” friends and it was so awkward because I watched him play the entire time…I was in a boot 😩 How rude, and that was our last date!

  • Kelly Hoover

    This is just TOO funny! I love this post!

    Happy Monday!

    Kelly Ruth

  • Hannah

    These are GREAT! Once, I was on a second date with a guy and his phone rings. It was another girl calling to FaceTime him… And he answered and had a full on conversation with the girl. 😂

  • Keri Elaine

    These are hilarious and I can’t believe a guy was rude enough to as for a Venmo after.

  • Carly Guggenheim

    Hah these are hilarious! The food poisoning one happened to me except it was the first time meeting his parents and sister… and in a parking lot! 😖😂

  • mariah

    what camera do you use for you blog and what blog website do you use?

  • mariah

    what camera do you use for your blog?

  • mariah

    also what blog website do you use as well?

  • mariah

    also what blog website do you use for your blog

  • Davida

    OMG this was too funny! Thanks for sharing!

  • Anna

    I laughed out loud reading these! Amazing post hahaha!

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