7 People Describe The Weirdest Date They’ve Had

by Natalia Lusinski

I don’t think I’m alone when I say I’ve had some weird dates. You, too? But what is the weirdest date you’ve had? And did it lead to another one? After all, maybe the person was nervous… or not. One of my weird dates was even televised on Blind Date . But what’s a girl or guy to do when we find ourselves on a weird date?!

“If the weirdness was circumstantial, then give him/her a second chance,” Rhonda Milrad, CEO & Founder of Relationup, Relationship Therapist, tells Bustle. “If weird means that your date took you to a terrible club to hear awful music or made a strange restaurant choice (like a Moroccan restaurant where you tried to sit on an oddly shaped sofa with high pumps and were constantly interrupted by belly dancers pulling you up to dance with them), then yes, give the person a second chance! It may turn out that the odd things that they chose were great examples of their creativity, their risk-taking, and their joie de vivre that you will come to love about them.”

True. So let’s put the above into context. With one of my weird dates, I’d met the guy a few times first through friends and there was nothing weird about it. But when we finally went out one-on-one, The night we were supposed to go out, he forgot about his dad’s birthday party — only, I was already in his car when he mentioned it. So, yep, not only was I meeting his dad on our ~first~ date, but we were also going to the county jail (!) for the birthday party, where his dad worked.

Oh, I forgot to mention the tour he and I got of all the jail cells where famous people had stayed (this was L.A., after all). Nothing like some comedy sprinkled into an already semi-awkward situation — i.e., “Hello, my date’s father. Nice to meet you.”

Afterwards, my date and I got stuck in the parking garage of the jail — neither of us had cash for the parking attendant, and she insisted on cash. Luckily, I found a bunch of pennies and nickels in the bottom of my bag to get us out of jail… literally. He and I ended up dating for a few months — and often laughed about our almost-getting-locked-in-jail story — so you never know.

But “weird” has different meanings for different people. “If the weirdness was due to their personality, then don’t be cajoled into a second date,” Milrad says. “If you felt that your date was odd (told inappropriate stories, revealed way too much too soon), or acted in ways that were antithetical to your values (rude to the waiter, sent back their food many times, complained all night about everything), then you have learned enough about your date to disqualify them for a second. It’s always good to listen to your instincts when you get red flags.”

Below, you’ll find seven people who shared their weird date story.

1. Rachel, 29

The weirdest date I ever had was at the Rainforest Cafe — I honestly thought it was a joke because the guy said ‘he had a great table reserved by the monkeys.’ Little did I know, he ended up picking me up and driving me over there. Once we were seated, we launched into icebreakers, and within 10 minutes, there was a ‘thunderstorm’ (hello, this is the Rainforest Cafe, after all). The monkeys were going wild, and my date got super awkward about it and started saying how he regretted bringing me there. You don’t bring someone to Rainforest Cafe without conviction. Could have been a fun date if he had more confidence.”

2. Mars, 26

“The weirdest date I ever had was when I threw a fake wake for my former roommate. He wasn’t really dead, but moved to New Mexico, so we all knew we’d never see him again. I decided to throw a wake for him, inviting all his friends over to share some fond memories. I also had a crush on this girl he had been speaking to, so I kind of turned it into a date. Turns out dressing in funeral attire, drinking way too much, and sharing stories around a shrine you made of your old roommate makes for a pretty fun date.”

3. Bryan, 36

“Dating and running a fast-paced and growing tech startup is daunting. I’ve tried all of the apps with varying success. The weirdest date I ever had occurred a couple of summers ago when I picked up my date at her apartment building and the first thing she asked me is if I would record her doing the Ice Bucket Challenge. That’s right, this person I did not know had me video-record her with her phone, dumping an entire bucket of water on her head — after which, she dried off and we went out to dinner. She was a cool person, and perhaps she was just testing me to see if I would go with it. We’re still friends (on social media), but I would have to say it was pretty weird. Plus, there was not any real chemistry there to continue seeing each other.”

4. Mariah, 22

“The weirdest date I ever had was when I met a guy from a dating app that was already four beers deep when I arrived, and continued to drink 10 additional beers and five shots of Jameson. He followed up the next day with, ‘I didn’t make you pay, did I?’ THANKFULLY, he was drunk enough to not bat an eye at the $300 tab!”

5. Michael, 26

“The weirdest date I ever had was my first date with an older gentleman. We spent the evening drinking wine and watching movies at his house. It was nice! Until he mentioned his ex-boyfriend, who — surprise! — had just moved out the day before. After 30 minutes of trash-talking his ex, he said that I seemed different — refreshingly genuine. He invited me to move in with him so that I could quit my job and focus on writing (I write and vlog about relationships). This was not my kind of crazy. I chose to wrap up the evening and asked him to lose my number. After a couple days of non-stop texting and calling, he finally gave up.”

6. Robin, 40

“The weirdest date I ever had was with a guy we will call Nick. He had a dog we will call Chanel, who had her own Instagram page. I went over to Nick’s house and he showed me a box with Chanel’s wardrobe in it. Later, as we sat on the couch, Chanel kept jumping between us and started nipping at me and nudging me out of the way. Nick proceeded to have a full-blown conversation in baby talk with the dog. I had previously mentioned my love for gummy bears, and Nick proceeded into the kitchen at some point, picked up a bag he had bought for me, and shook it in the air at me like a treat for dogs. I proclaimed soon after that I had to leave and realized I wasn’t a good girl and never got my gummy ‘treat.’ You can safely assume this was the last date, as the creep factor was high with this one.”

7. Nadia, 30

“The guy swore he was the same age, but looked about 15 years older. He asked what each my parents did professionally and proceeded to tell me what was wrong with women who worked. That was the only date I pretended to be sick and left.”

Overall, should we give second chances to weird dates?

“I say give it another try, as long as the ‘weird’ in question doesn’t feel unsafe,” Molly Lizzio, Licensed Marriage and Family Therapist, tells Bustle. “Always follow gut feelings when it comes to intuition around safety. If it’s safe and just not a great start, give it another try. We get so wrapped up in what's it’s supposed to look like that I think we can sometimes really miss it when it doesn't look exactly how we expect it to."

Images: Andew Zaeh for Bustle, Giphy