Sex & Relationships

Think Your Ex Was Bad? Read These Terrible Dating Stories

Friends of FLARE rounded up their legit worst dating experiences—all for your enjoyment

A photo from the series Friends where Rachel is on a bad date with Jon Lovitz

(Photo: Getty Images)

Dating can be the worst.

Between deadbeat dudes, f-ck boys, ghosting and straight-up terrible first impressions, getting to know someone romantically can leave you feeling… drained. Just watch any season of The Bachelor or The Hills if you need further proof. If you’ve ever felt like love is a battlefield loaded with shitty dudes waiting to stomp on your heart while making you pick up the cheque (or at the very least waste your precious time), have no fear—we’ve all been there.

In that spirit, some friends of FLARE generously agreed to share their most terrible dating stories. From not-so-discreet hook-up requests to poop-stained PJ pants, here are tragic things that have happened to us IRL. You’re welcome, and no, we’re not sorry for sharing.

Unforgivable first dates

A GIF of a guy on a first date

(Source: Giphy)

The guy who valued “experiences” over “things”

The Starbucks date didn’t start off terribly—he was about 5 inches shorter than he’d claimed to be, but was also WAY cuter than his profile photo, so I felt like it all balanced out. (And to be clear: his actual height is a non-issue; lying about it was the downside.) But when we actually started talking, I felt like all this dude wanted to do was prove how ~*intellectual*~ and different he was. Strike one: He said he preferred to spend his money on experiences rather than things. I agreed, and started talking about my love of travel—at which point, he interrupted me to say I probably “still owned Uggs though”… and then he LOOKED AT MY SHOES TO SEE IF HE WAS RIGHT. At that point, I realized I didn’t need to wait for three strikes. I immediately came up with an exit plan: I needed to pick up a gift for my niece at Sephora. He followed me to the store, sharing his thoughts on makeup and opinions on girls who wear too much of it all the way. We did not go on a second date.—Stacy

Date rating: 4/10 

The guy who was next-level creepy 

My foray into online dating wasn’t exactly what I expected. Prior to this particularly horrendous date, I’d only met someone from Tinder once (he was a bouncer at a club I frequented and we played Mario Kart for two dates before calling it quits). After hearing a few success stories, I decided to give it a shot again. I was 24 and living with my parents and figured new year, new me, right? WRONG. My Tinder date, first of all, showed up to our date spot—a Timothy’s Cafe—unfashionably 30 minutes late. He then proceeded to tell me about his anti-sex Catholic upbringing, his desire for a homemaking wife and his penchant for feet. I am not one to judge people for their fetishes but, correct me if I’m wrong, this defs wasn’t a first date talking point.

The date ended with a somewhat unwanted sloppy kiss beside my parents’ van in the parking lot, and a strong desire to never see this human being again. Turns out, he had other plans. I’d let it slip where I worked, which was a fair distance from where I met him and where he lived. A week later, he appeared at my place of employment… for a—wait for it—interview. He reached a whole new level of creep. Once he got hired, I requested shift times that did not overlap with his. Eventually, he got fired for harassing a client, which I warned my boss about at the time. Hate to say I told you so, but… JK, I love it.Meaghan

Date rating: 1/10 (the tea he bought me was good, so the “1” is for Timothy’s)

The guy who wanted one thing…

When I was 17, this guy from the high school across town would not stop texting me. I wasn’t super into him, but when you’re 17, WTF do you know? (I’m 22 now, so I consider myself extremely wise without anything left to learn #JustKidding). Anyway, this dude kept asking me to hang out at his house—which I was not at all interested in—so I switched it up and asked him to meet me at the local coffee shop. I figured, this way, I could see if he was down to talk or if he just wanted to hookup. Unsurprisingly, it was the latter. He texted that something abruptly “came up” when I’d already been at the meeting spot for 30 minutes. The kicker? We went to the same party a few weeks later, and he a) acted like nothing had happened, and b) tried to make a move. Gross, huh? —Meghan

Date rating: 5/10, because even though it didn’t happen, I’m sure it would’ve been weird

The guy who wanted to reinvent the dishwasher and hang with Obama 

After online dating for a while, I was so over exchanging endless text messages before actually making plans for a first date. Instead, if a dude seemed to have decent spelling and a job, I was down to meet up and decide in-person if there was something there. I set up one such first date at the pub down the street from my house. In the hour leading up to the date, my phone would not. stop. buzzing. “I’m driving to the subway station,” my date wrote. Fifteen minutes later: “I’m getting on the subway.” Twenty minutes later: “I’m getting off the station.” Two minutes later: “I’m walking up the street.” Cool story bro, just get here. 

And then he did—wearing grey sweatpants and a Bob Marley t-shirt. We sat down in a booth and he immediately starting talking about everything from his childhood to his job. I started ordering doubles. Clear that this wasn’t going to be a two-way conversation, I went into interview mode. He mentioned that he was an inventor at heart, and that one day, he was going to be so successful that he would be in a photo with the then-U.S. president Barack Obama, pointing at his new bud and saying, “Yeahhh, this guy!” 

OK, so what are some ideas you have for inventions? I asked. He proceeded to tell me about how he wanted to revolutionize the typical kitchen, constructing a wall with a variety of different sized slots in it. Each slot corresponds to a particular type of plate or bowl (Note: the related dishes had to be bought separately from the kitchen reno, but as he explained, that would be a “one-time purchase”). After eating on these dishes, the user would put it into the appropriate slot where it would go into the wall, get washed, dried and put away. And he called it the “T-Wash” because his name was Trevor. THIS IS A DISHWASHER BUT SO, SO MUCH WORSE. 

When T-Wash, as he has now become known, got up to go to the bathroom, I texted my friends to tell them the date was a dud. They agreed to meet me at the subway station and when T came back, I informed him that I had to get going. “Well, this was fun, when can I see you again?” he said. “Um, thanks but never?” I responded, trying to catch our server’s eye (I wasn’t about to stick him with the bill for my drinks after a short AF date that ended with me bailing). For some reason, even though we were basically the only ones in the bar, the server took her sweet time coming over to us and as a result, I had to sit there and, at T’s request, explain why I wasn’t down for date numero dos. (Fun fact: It turns out that he changed from his work clothes into sweatpants because I “seemed like an easy-going chick.”)

As soon as my debit payment went through, I waved goodbye and booked it out of the bar. It was only when I was recounting this story to my friends later that night that we realized, T was stoned the entire time.Ishani

Date rating: 4/10

The guy who lived for a thrill

In the summer between my third and fourth year of university, I went on the worst date ever. After a night out, we were heading back to his (read: parents’) place and stopped into a bagel shop for drunk food. After ordering, he said “watch this” and proceeded to steal a package of smoked salmon from the fridge and put it in his coat. I was too scared to do anything, so I quietly waited for my food and got out of there ASAP. The rest of the walk back was spent listening to him talk about how he and his friends always do that between shovelling pieces of smoked salmon in his mouth. I was SO ready for bed by the time we got to his house, but JK there was no bed for me and apparently not even a couch. Instead, he led me to a sleeping bag wedged between a treadmill and a toy box in a basement that looked like it was straight out of a horror movie. I obviously couldn’t shut my eyes and I debated leaving to sleep in my car… but I was too afraid I’d wake his parents. Erinn

Date rating: 3/10 because the bagel (which I paid for, BTW) was pretty damn good

Bad boyfriends 

A GIF of reality star Justin Bobby

(Source: Giphy)

The guy who couldn’t keep it out of his pants 

I was in my early 20s when I dated a much-older dude who swept me off my feet despite countless red flags, like excessive drinking and the hydro he “borrowed” from his building’s hallway via excessively long and obtrusive extension cords. We dated for a couple of months until I was unceremoniously ghosted. Keep in mind, the trauma of an early-aughts ghosting was far more severe than present-day ghosting because you couldn’t keep tabs on an ex via social media: If you didn’t bump into them IRL or sad gal-call them, they were legit gone.

I moved on and eventually my roommates and I moved to a new apartment where we decided to make some extra drinking money by holding an impromptu yard sale. We set up piles of stuff on our curb and I decided it was high time to pull out the “ex file,” a.k.a., the box of his junk that I’d had moved from one apartment to the next in the tragic hope that he’d call someday for a do-over. A passerby giddily snapped up his Polo Ralph Lauren pyjama pants for a cool $2 before returning minutes later with a look of pure shock on her face. She handed me the pants and asked me to look inside. There it was, on one of the last artifacts of our crappy relationship: a shart stain. I wordlessly gave the woman her toonie back, threw the soiled jammies in a sewer and collapsed in laughter with my two best friends. And to think I always hoped he’d get his shit together.—Jenn

Date rating: 0/10 for literally being the shittiest boyfriend ever 

The guy who was just an ass

We’d been dating for about a year and, admittedly, I had gained bit of weight. I went over to his house to hang out, as you do when you’re 17 and have zero income, and after watching literally hours of him play Xbox, I was hungry (GOD FORBID). I went for a handful of cheese puffs to which he replied, “Exactly how much weight have you gained?” Mother f-cker. I WISH I had replied: “180 lbs of asshole.” —Alanna

Date rating: –180/10 

The guy who wouldn’t take the fall

I went to university on the east coast in my mom’s hometown, and she would occasionally drive out from Ottawa to visit me and the rest of her family. One spring, she made the trip in my dad’s brand new, super shiny Cadillac, but didn’t want to do the return trip. So, she flew back, and my then-boyfriend and I decided we would take on the 17-hour journey. Everything was going totally fine, until one particular pit stop. I went into a cheese shop in Quebec, solo, and came out to find him scratching at the hood of the car with the back of the keys. I asked him what the hell he was doing, and he said he was trying to get bird poop off of the hood. Like, fine, but with the back of the keys?! Needless to say, he left a pretty noticeable mark in the paint, and we spent the rest of the drive stressing about how we were going to fix it and what we were going to say to my dad who was waiting for us in Ottawa. Fun side note: my dad was about to meet this boyfriend for the first time. We ended up deciding that I would take the fall, because my dad had to love me, you know? When I told him, he asked me how I could be so stupid. “I honestly have no idea,” was my response. Eight years later, and three years after the end of that relationship, I finally told my dad it wasn’t me… but he said he knew all along.—Tara

Date rating: 3/10—only because it made for a good story

The guy who was a hot, drunk, poetry-loving mess

Let me preface this story by disclosing that this experience happened during a dark, dark period of my love life.

I was walking into a dive bar with a friend on a chilly Saturday night a few Decembers ago when she bumped into a co-worker outside. Her co-worker was with a group of his pals, and one of them was particularly intoxicated and tragic: he introduced himself to me by revealing he had just been dumped. I was trying to be polite and made small talk about how relationships are the worst la la la la. If that wasn’t enough of an overshare, he then said he was really into poetry (?), and started reciting a monologue from the Leonardo DiCaprio version of Romeo and Juliet, in what I assume was an attempt to woo me. Please keep in mind NONE of this was prompted as I had legit just met this dude on the sidewalk.

I still cannot understand why on Earth I gave this man my number, but before we parted ways, I forked over my digits. In the second stupid move of this story, after he texted me, I agreed to go on a date with this weirdo. I invited him to meet me at a New Year’s party a friend was hosting at a venue. Like the time we first met, he showed up drunk. Now realizing the mistake I had made, I excused myself to the washroom and left him at the bar. As I was leaving the washroom, I heard a huge scuffle and saw bodies jumping in to break up a fight. I ran to see what was going on and LO AND FREAKIN’ BEHOLD my date was being dragged off another partygoer. Naturally, the party’s bouncers kicked him out. I wish getting booted out of a bar was enough to turn me away, but like I said, it was a dark time in my life. We went on a few more dates until he ditched our dinner plans last minute because “he had a stain on his pants and needed to wash them.”

I’m happy to say we no longer speak. Laura

Date rating: 2/10 (I love Leo)


“Why I’m Giving Up Dating Men and Just Staying Home”
Three Types of Guys I’ve Met Dating Online as a Single Trans Woman
It’s Tough Being Black on Tinder, But I’m Not Giving Up
What It’s Like Being Aromantic on the Most Romantic Day of the Year