Ah, dating. It can be fun, it can be tiring, it can be exciting, it can be discouraging. It can make your heart swell; it can make a pit form deep down at the base of your stomach. It’s one big swirl of emotions all mixed up into the messy experience that is life.
On this Valentine’s Day, we’re bringing you our team’s worst dating stories—because maybe we’re a bit cynical, because maybe we’ve all been there (“there” being sitting across from a new someone wondering how they’re so different than we thought they’d be), because maybe it’s nice to know we’re not alone in these experiences. The stories below are made up of one part cactus, one part tampon (not combined, oh my god), one part voice memo, one part SportsCenter (on a date…how!!!), one part shameless negging.
After you read ours, we want to hear yours in the comments!! Let’s all give the uncomfortable, awkward moments that once made us cringe new life as ones that now make us laugh, and make us collectively feel less alone.
From our team to you, Happy Valentine’s Day.
Not necessarily a bad date story, but this sums up my overall dating experiences.
In exchange for playing wingwoman for a good friend of mine, she’d usually score us a few free drinks, which was perfect for two broke, recently postcollege ladies. We went to a somewhat notoriously d-bag bar, hoping to score a few free drinks on a Saturday night.
An attractive guy came over, introduced himself as X, and offered to buy her a drink. She accepted, on the condition that he buy a drink for me too. This guy wasn’t exactly her type, and I could tell that she was getting bored, so she “had to use the bathroom” (ladies, you know) and left.
Assuming she’d be right back, X reluctantly struck up a conversation with me. I could tell he was incredibly bored (and quite frankly, so was I, but I had just gotten a drink, so I muddled through).
He got my number and I was really excited until X said, “I should’ve been talking to you from the beginning. I told my friend I was going to hook up with the hot girl at the bar (motioning to my friend).”
Little by little, the conversation got interesting, and X continued to talk with me after my friend returned (and had moved on). At bar close, we were laughing, and it felt as if a connection was forming. He got my number and I was really excited until X said, “I should’ve been talking to you from the beginning. I told my friend I was going to hook up with the hot girl at the bar (motioning to my friend).”
And with that, the night was over.
New Business Director
Three words: seven. hour. date. Seven hours!
First up was dinner with dessert, then we met up with friends for a movie, then we went back to the friend’s house and proceeded to watch SportsCenter, twice in a row. Did you know that after one episode finishes they play it again? Because they do, or at least they used to when this date happened.
It ended with an awkward hug and I’d guess my date said a total of fifteen words the entire evening.
I was dating this nice young man when I was young, maybe sixteen years old. He was the most polite, well-spoken band nerd I could find—a dreamboat. Things were great, and we did all the fun things that Willmar, MN had to offer like walk our dogs and occasionally go to Applebee’s after 9:00 p.m. for half-off apps.
I really enjoyed his company but eventually, I fell out of “like” with him. He meant so much to me and I had never broken up with anyone before! What was the protocol? What makes people happy? Gifts. Yes. Perfect. But what is a good “I only see you as a friend” gift? Easy. A cactus. So, yes, I broke off a piece of my mom’s cactus in the living room, potted it, and drove to his house. I gave him the cactus, broke up with him, then headed home.
I of little dating experience dove headfirst into dating last winter, and from February through July, dating was one of the primary extracurricular activities in my life. Out of all of them, the date that stands out most began where many of them did: on Tinder.
Brian (not his real name!!!) was a writer, too, and a journalist, and we began a nauseatingly in sync back-and-forth stream of messages. We switched to text, the banter continued, and a date was set for Sunday evening.
The downfall of our shortlived dating experience began before the date itself. When we set the date, we hadn’t outright picked a location, but we had settled on a time: 6:00 p.m. The day of the date came and after a looong string of texts, we finally settled on a spot (Fair State, for you Twin Cities locals who want to set the scene!).
By now it was 6:05 p.m. I texted him “Are you heading over there now?” He replied with a voice memo (!!) saying he got caught up with something and would let me know when he was headed that way. Twenty minutes later, I got the “headed that way” text, followed by another voice memo letting me know that “the only thing I would add is that I’m twenty minutes away and you’re probably closer, so a heads up on that.”
By now it was 6:52 p.m., I’d been sitting at my apartment, ready to go, waiting on him for over an hour, and I had already texted and had a subsequently enraged FaceTime conversation with a close friend. I almost canceled the entire thing altogether, but I’d been particularly curious about this guy, so I went.
He was generally nice and mildly intriguing, but the banter in person didn’t match the initial version on the app, the chemistry wasn’t there, and I was never going to get over his nonchalance about wasting my time before we’d even met. Because folks! We all deserve better than that.
The date started at 7:20 and was doomed from the get-go. He was generally nice and mildly intriguing, but the banter in person didn’t match the initial version on the app, the chemistry wasn’t there, and I was never going to get over his nonchalance about wasting my time before we’d even met. Because folks! We all deserve better than that.
I was less charming than I’ve been on any other date by far, and afterword, shockingly, I still got a text that he was impressed (?) and wanted to take me out to dinner. Needless to say, I declined and haven’t spoken to him since.
Creative Director, Founder
1) I sat across from a guy who had the BIGGEST DANGLING BOOGER EVER while I watched him eat a plate of sweet and sour chicken. I told him he had something hanging from his nose and he got all defensive and cut the date short. I guess “snot” everyone can handle the truth.
2) It was Thanksgiving and I was at my boyfriend’s parents’ house. They had a septic system so you couldn’t dispose of feminine hygiene products in the toilet. Over pumpkin pie, I saw my boyfriend’s brother’s dog drag something small along the floor and drop it in the middle of the living room. IT WAS MY TAMPON.
His brother saw it, GRABBED IT WITH HIS BARE HANDS, and ran off with it.
I have never been the same.
7 Lessons I Learned While Finding Myself
The Stigma of Singledom and the Digital Dating Era
Joe’s Advice on Dating, Compromise, Effective Communication, and More
The Most Important Questions You Needs to Ask Before Moving in Together
Six Solo Dates to Schedule Stat
I’m in Love and It’s Really Boring
Owning the Ebb and Flow of Your Relationship
Jackie is the editorial director at Wit & Delight. In her spare time, you can find her running around the lakes of Minneapolis, grabbing a bite at a local restaurant, or recharging at home with her boyfriend and their beloved corgi, Marge. You can follow her on Instagram @jackiesaffert.
BY Jackie Saffert - February 14, 2020
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Thank you for being here. For being open to enjoying life’s simple pleasures and looking inward to understand yourself, your neighbors, and your fellow humans! I’m looking forward to chatting with you.
Ready for this one? Well, I was in my 20’s and doing the online dating thing. I met this guy who seemed cool via email and we arranged a date. I had been really sick with the cold and flu shortly before and even had to reschedule because of it. We did dinner and after the date, I went back to my car and ended up having to stop on my way home to vomit. Not over the sickness yet, clearly. It gets worse. We had a second date which was also fun – hit up a museum and dinner… Read more »
Susie. SUSIE. Oh my god. That is a rough one, but as with all bad dating experiences, it makes for a good story, yes? No? Maybe? I think so.
Every single guy I’ve dated has been discussed, at length and often in *vivid* detail, with one or more of my friends—it’s not weird in the slightest that those minute details were broken down with your coworker; it’s just the biggest bummer that the guy found out. Thank you for sharing your story with us!! And may copy/paste never betray you like that again.
These are great, thank you for sharing!
Thanks for your comment, Odessa! Glad we can all laugh about our bad dates now. 🙂