Our 10 Best Accidental Dates

Twenty-Something Tuesday

It’s spring, and love is in the air. Sometimes the best romantic moments happen when you least expect them. They are made all the more beautiful by your lack of planning, and maybe you never feel better than when, in the poetry of Drake, you got your hair tied/sweatpants/chillin’ with no makeup on. Here are a few couplebrags for those of us at LD who have loved those non-date nights.


The Time We Got Lost In Pittsburgh

For our first date, my now-husband and I decided to go up to Mount Washington in Pittsburgh. For anyone who’s unfamiliar with the ‘Burgh: Mount Washington is a hill on the opposite side of the river from downtown, where you can take “the Incline” (which is like a sort of tram that goes right up the edge of the hill) to a lookout point with the most beautiful views of the city. We took a bus downtown, then a train that would supposedly take us to the Incline. Well … we couldn’t find the damned Incline. We ended up walking for three hours around strange neighborhoods in the dark, talking about everything in that exciting first-date kind of way. Eventually, we found ourselves walking up a hill and Google Maps was telling us we were on the right track to find the Incline. We came out on top of the hill … and realized we’d walked all the way up a weird back route to the TOP of Mount Washington. Not an accidental date per se—oh, it was very much a date—but this accidental blunder set the tone for a most perfect, derpy relationship.


 Accidental Pittsburgh Date II

The last date I went on with my husband was also in Pittsburgh. This time around, we returned as triumphant Young Professionals (hur dur) and stayed in a fancy hotel downtown, because why not? After a very heavy night of drinking, we woke up late and realized we needed to get back home to Virginia, since real life was calling n’at. But first: we needed hangover food. We sat and laughed hysterically about nothing in our hungover delirium over a feast of McDonald’s fries, got coffee, smoked cigarettes by the river, dipped our feet in the (freezing cold) fountain, bought souvenirs, and wandered around for five glorious hours. I asked him a very silly question about the job he’s been doing for months now, and suddenly, secretly felt transported to that first-date-fluttery feel. We ended up getting home really late that night with a mountain of work to catch up on, but the accidental Pittsburgh date was entirely worth it.


Hallowe’en to Hallowe’en

A couple of months into my year abroad in North Carolina, I went to a Hallowe’en party and got chatting to one of the guys who was hosting. Actually, I was dressed as a dark angel, and I accidentally hit him in the face with my halo as I walked by. It’s a cliché, but from the moment we met, it really did feel as though we’d known each other for years. We sang Beatles karaoke, debated over Aaron Sorkin shows, then got Jimmy John’s sandwiches and stayed up talking until 4 a.m. It really wasn’t a date, though we did become boyfriend and girlfriend a year later. But it was definitely the start of something big: We’re getting married next Hallowe’en.

– Jodie

A Cute Date with Cupcakes

I had a huge crush on this guy for months. We had hung out a lot in our larger group of friends, but had never hung out alone and I was dying to get some one-on-one time with him. One day, out of the blue he texted me saying he was in my area and asked if I wanted to meet up and hang. Obviously I was ecstatic, and he asked what I wanted to do. I was craving cupcakes, so he picked me up and we made an impromptu trip to DC for Georgetown Cupcakes. We spent the rest of the afternoon exploring the city and hanging out. No, it wasn’t an official date—I admit that I did hastily run up to my room to look a bit nicer, and my Dad called me out on blushing, but neither of us entered that day 100 percent sure as to whether we were hanging out as friends or as more than friends. However, I had a fantastic time, so I texted him a few days later to go on a real date—and we went on to date for a year and a half after that!


Burgers on the Side of the Road

My adorably accidental date happened on the way to a “real” date. My boyfriend and I made plans to go on nice, official dinner date out to balance our days on end spent at home watching Netflix in our sweats. We both planned all week to make this a real night out. We had decided to go to dinner on a Friday night, only to realize that the restaurant, that didn’t take reservations, had an hour long wait. We were starved, and with one “Are you sure you want to wait that long for a ‘real’ date?” look, we were off to the closest drive-through burger joint. Rather than take the food home and spend yet another night on the couch we drove around for half an hour looking for a park bench or something to picnic on. After finally finding something, we got out of the car and were hit with a cold, blustery wind that made eating outside no possibility at all. We ended up sitting in my car on the side of the road, eating fast food straight out of the bag, laughing, talking and being silly as ever. Even though we planned to go on a nicer date, this favorite romantic memory happened out of those plans falling apart and us appreciating the only thing that really matters on a dateeach other.


The Second Date of the Evening

I went on a Tinder date one weekend and we really hit it off. We were constantly texting but, you know, Tinder, so I wasn’t about to cancel the dates I had already set up—especially since he was going out of town. So come Saturday night, I was on my way to another date, but I texted him to ask how his trip was going, and he replied that he had actually come back early. I realized he was really the person I wanted to spend time with, and in the texts during my sneaky trips to the bathroom, he offered to meet up at a bar across town at 11pm. I made some lame excuse to the date and bounced. Due to festival traffic, I didn’t actually get to the second bar until midnight, but as soon as we sat down we were completely absorbed in each other. We barely even noticed when the bar closed at 2 a.m.; outside we kissed for the first time and I floated back home. Later I found out we met up WAY past his 9:30pm bedtime and he was already lying down, in pjs, but mustered up the energy to come see me. That was six months ago, before I wrote this about him, and he still waits for my punctuality-deficient ass and I still float after seeing him.


There’s Always Time for Prosecco

My exboyfriend in Italy was a lot of things, not the least of which were playful and spontaneous. One afternoon early in the relationship, we were running errands or something and he basically said, “Fuck it, you want to get a drink?” We put everything on pause, found a bar, and got a couple glasses of prosecco. I just thought it was so glamorous to stop being busy in the middle of the day and indulge in some bubbly. I mean, why not?


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Chicago Pride Parade 2013

The first year I lived in Chicago, I was big on experiencing every major parade, street festival, 3 p.m. bar crawl I’d ever heard recommended. One of our biggest, and really, best, events in the summer is the Chicago Pride Parade, which I was super excited to see for the first time. I’d made plans to go to the whole thing with my gay best friend, but he canceled that morning, so I called Doug, this guy I was casually seeing/make out with, to see if he wanted to go. Doug turned out to be the greatest parade companion—at 6’7, sitting on his shoulders meant I could see everything despite the rows of people in front of us. After the floats went by, we headed to the beach, which was basically empty since everyone was still swarming the gay bars, and laid together in the sand on the most perfect sunshine-y day, with him being an amazing sport about me kicking sand on his face. TL; DR, Doug stopped being my back-up plan after that day, and he and I have been together since.


Nasty Beer, Tasty Tinder Date

Ever since I broke up with my year-long boyfriend about a month ago I’ve been Tindering it up (because yes, Tinder has become a verb). I never thought I’d be on Tinder but I’ve actually had tons of fun and some great experiences. That’s right—I regret nothing. It was a Saturday morning and I was chatting with a cute tall guy (bless the tall men). He was nicely up-front about the fact that he was from out-of-state and only in town for the weekend for work, and would I like to just hang out? Cute guy, no expectations so I can just be myself, alcohol, and out on the town on a gorgeous night? Yes please! We went to this awesome taphouse that has a jillion beers (I know nothing about beer) and I was like, “This one has a cool name so I’ll try it!”, but of course it was terrible. I get another (better) beer, we drink, we talk, we laugh, and we exchange Tinder horror stories. We walk around, get more beer, he convinces me to dance (which only happens with alcohol and consists of jumping up and down), and bam we’re making out against the bar’s wall and it was fabulous. And I was not expecting that at all, which made it all the more fabulous. We say goodbye at the end of the night and I might never see him again. But, darlings, consider me a convert to spontaneity.


Accidental Summer Concert

My current manfriend and I were on our second date, and things were really going well. He had met me at my office after work and we wandered to a Thai restaurant downtown for dinner, where I miraculously pretended to be tough enough to handle the spice level. Our first date had been surreal: five hours of nonstop conversation that kept us up until 3 a.m., stunned that we had found each other. But second dates are always trickier, especially when the first one sets such a high bar. Still, the conversation during dinner flowed naturally, and we moved to a nearby park after to continue our chat. Just when we were starting to feel shy and a little unsure of what our next move would be, we noticed a crowd gathering toward one side of the park. As luck would have it, our city’s coolest outdoor concert venue was hosting a free concert that night. We lounged on the grass as night fell and admired fireflies to the sound of acoustic guitars. It was a perfect night that foreshadowed a great year to come.


Dinner at Home

My current relationship (1 1/2 years so far, go us!) was founded on a regular casual hookup schedule that began in my junior year of college. We met as friends through mutual friends until one night when Jagermeister stuck its licoricey finger into our fate and prompted a sloppy 4 a.m. makeout. After that, we stayed friends, simultaneously taking advantage of the “benefits.” After coming over just for hookups got old, we eventually got more creative with our evenings. One night, I ended up making dinner for him from my freezer stock of my mother’s pesto sauce on angel hair pasta and some frozen veggies. Simple college fare, which we paired with a private bedroom screening of “Juno.” It was a typical dinner and a movie date long before I recognized that we were dating. I actually continued to ignore the steadily blooming relationship through the many similar nights in the weeks and even months to follow. It took a whole lot of distance (three months spent 5,000 miles away) for me to realize who I really wanted to be closer to. I still count that night as our first date, whether or not we intended or anticipated it to be.


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