The hottest days of the year call for a Summer Fling. This week, we're deep-diving into sex, dating, and relationship drama, here.

By Maria Del Russo
Jul 28, 2018 @ 5:00 am
Dearest Creative

If you’ve been on enough first dates in your life, you know that most of them are just fine. You get dressed up, you meet someone at a bar or a restaurant. You chat long enough to figure out if they're the type of person who keeps their cereal boxes in the fridge. If they’re not, you agree to a second date. And even though things often don't remotely resemble a romance novel, some of those "just fine" dates will lead to everlasting love.

Then there are the dates that go terribly: stilted conversations, awkward kisses, sweaty palms, and the occasional lost wallet or peed bed. And you know what? Some of those end in marriage, too. If you're single, you may think all your married friends met in some made-for-TV meet cute, the likes of which will never happen to you. But married folks often think back to their first dates as the same awkward, bumbling misadventure as everyone else's. There's something hopeful in that.

Don’t believe us? Ahead, find six less-than-perfect first dates that, seemingly in spite of it all, eventually led to “I do.” Keep these in the back of your mind the next time you’re hiding out in the bathroom, texting your friends about the nightmare first date you’re currently on. You never know — that nightmare could be your one great love.

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A Ghost of Bad Dates Past

I met Keith on a dating website a few weeks after a terrible breakup, attempting to get back in the game. We chatted for about two weeks before he texted that he would be at a bar in my neighborhood and I should meet him for what would be our first date. When I got there, he wasn’t alone — he was with three coworkers. After a few hours, his coworkers left, and Keith took me to his favorite bar in the area, where he exclaimed that his friends were not going to believe he found a “girlfriend.” And just like that, the night went from possibly salvageable to one of the most awkward of my life.

Keith reached out a few days later to ask me out again. And since I believe everyone deserves a second chance, I said okay. We went to dinner this time, and it was somehow more awkward than our first date — conversation was dry and stilted, and weirdly annoying. After that, we mutually ghosted one another.

A year and a half later, I had signed up for a singles’ trip to Israel. At the orientation, I spotted a familiar face — Keith. There were safety issues in Israel at the time, but knowing I had a connection to home through Keith made me feel safe, even though we had been keeping things platonic. During a particularly scary night that involved us being evacuated from our hotel, Keith grabbed my hand and told me we’d be okay. Something clicked in that moment. I started to see him in a different light.

Four days after we got back, Keith asked me if I wanted to give it another shot. Nine months later, we were living together, and five months after that we were engaged. We’ll be married two years in September. —Lindsay L.

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Wasted Youth

Jason and I went on our first date in the winter of 2009. We were in college, so we went to a volleyball tournament and then out to dinner. During the tournament, he introduced me to his friends as Natalie. (My name is Nicole.)

After dinner, we headed back to his apartment to watch a movie — and make out on his futon. But while we were making out, his super drunk roommates burst into the apartment. They apologized profusely, but I was mortified. Jason went to help them into bed, and while he was helping them, his particularly loud friend continued drunkenly “apologizing” for barging in. During his speech, he said that he hoped I would give Jason a blow-job despite their intrusion.

I didn’t do that, but I did go on a second date with Jason, which went much better. Our three-year anniversary is in October. —Nicole S.

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So my husband and I met when I was 22 years old. I went out with a bunch of girlfriends to a bar, and our group started talking to my future husband’s group of friends. He and I started chatting and dancing, and there were a lot of Bacardi and Diet Cokes being consumed on my end.

I ended up going home with him that night — really drunk. I slept with him, and when I woke up he next morning, I had peed the bed because I was so drunk. I had no idea where I was, who the guy was, or what his name was. (I was able to figure out his name because he had a business card on his desk.) When he saw the pee mark, he just offhandedly mentioned that we must have been really sweaty. I think he knew, but he wasn’t going to embarrass me.

I was living at home at the time, and I didn’t want this seemingly random guy to know where I lived. So I asked him to drive me to my friend’s place who lived down the road. The conversation in the car wasn’t awkward. But on the way home, I realized I’d misplaced my purse — cell phone, wallet, everything. So when he dropped me off and asked how to get in touch with me so that he could see me again, I told him to text the phone in case I found it.

Later that day, my friends and I went back to the bar to see if I could find my wallet and phone. It turns out that they had the entire purse. They’d found it in a trash can. When I turned my cell phone on, I had a text message from my future husband, telling me he had a great time and wondering if I wanted to get together again sometime. I texted him back, and we went out to dinner a couple of weeks later and started dating from there. Now we’ve been married for seven years and have two kids.” —Claire M.

I woke up next to a guy after a blackout in Nicaragua. He asked me if I wanted to split a burrito and a spliff. I said yes. I didn’t remember how the conversation even started, but we are getting married at the end of the year. We’ve been together for five.” —Marissa B.

My fiancé and I dropped MDMA on our first meeting at the local pub. I tried to kiss her on the dance floor and she swerved — she swerved hard. —Brodie

Nervous Wrecks

My wife and I met online, and our first date was at the Tick Tock Diner in NYC. We were sitting there very awkwardly and kind of conversing when all of a sudden she starts crying her eyes out. I panicked, thinking something was wrong, and she insisted she was just nervous but the tears would not stop flowing. What was worse was the terrifying forced smile she mustered through the tears. The waitress packed our food and we took it to go.” —Deanna

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I ended a long-term relationship and, a few weeks later, confessed my crush to a coworker who said she felt the same way. I asked for dinner later in the week. I was stupidly nervous. I tried to think of everything. I rented some movies for us to watch, planned dinner at a nearby Chinese restaurant, and bought a sweater vest.

Holy shit, I had no game. I picked her up and fumbled through conversation. We barely spoke through dinner. It was awful. We eventually got back to my apartment, which was mostly cleared out because my ex owned most of the crap in it. We started watching a movie, and it’s just dense, London-fog tension. I ask if we could go for a walk to kind of air out some of the awkwardness.

I drag this poor girl around through neighborhoods for, like, three hours. In November. After way too much walking and being unable to make eye contact, we go back to my place. We sit back on the couch. I ask to hold her hand. I relish the minor moment of of triumph. I start to apologize for being so awkward and stammery. She says it’s okay. She looks me in the eyes and says "you got this." I kissed her. We were just married four days ago. —SnatchingVictory via Reddit.

 

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