They Had the Worst First Date (But Fell in Love Anyway)

Lindsay Goldwert
October 13th, 2020 | 6 min

Once upon a time, over a decade ago, I met my husband for our first date at a lovely outdoor restaurant and bar in New York City’s East Village. We laughed, we flirted, we ate delicious food. I was also so nervous that I drank too much white wine and nearly tumbled down a flight of stairs when I went to use the ladies bathroom. Our first kiss that night was magical… until a police officer got on his bullhorn and shouted, “Get a room!” (Rude!)

Was it the worst first date of my life? Nope, I definitely had worse. But there’s something sort of romantic falling in love with a person after a decidedly not-so-perfect initial encounter.

While I certainly wouldn’t wish a bad, awkward, or “I never want to see this person again” first date on anyone, they certainly make for great stories to tell your friends and family after the wedding. I'd rather listen to a story about nearly being clawed to death by koalas over a romantic walk on a moonlit beach any day.

Can a nightmare first date lead to a long-lasting love? These five couples told us about their worst first date was the beginning of something wonderful.

Worst First Date #1: “Losers in love”

The woman who would eventually become my wife and I had been friends for a little while before we started dating. We both worked in a library and saw each other all the time and joked around and stuff, but we were both in other relationships. Then she got dumped, and one night after work I took her out for coffee to try and cheer her up.

She was still feeling hurt about it, and I was doing my best to let her vent but then I accidentally spilled the beans about having heard that her ex had already moved in with someone new. I was doing my best to make her feel better but there she was, crying her eyes out. Then, literally a few minutes later, while we were still sitting there, my then-girlfriend called me up and dumped me over the phone. We spent that night talking into the small hours about our fates as romantic losers. Fifteen years and two kids later, we're still together, losers in love.”

-- Nathan and Allison, Meadsville, PA

Worst First Date #2: "In the car for two hours"

“We met online and after talking for five weeks, I was really excited to finally meet her. We decided we would go to New Hope, which is a cute little riverside town with lots of stores and restaurants, around 15-20 minutes from where she lived. After picking her up I took an extremely indirect route that had us in the car for two hours. I was completely on edge the entire time. If we hadn't built up a connection on-line and over the phone before then, I doubt there'd have been a second date. Luckily she wasn’t mad. Actually, she said it gave her time to get to know me.”

--Megan and Tom, Easton, PA

Worst First Date #3: “Nearly ripped to shreds by koala bears”

“We were both journalists in Sydney, Australia covering the Olympics. Somehow, though a mutual friend, we ended up at a dinner together where he learned that I had yet to visit Taronga Zoo and offered to take me there the next day. Because of our Olympic/press credentials, the zoo offered to let us in the Koala pen, which was a really big deal. The zookeeper took us into the pen and told us that it was okay to take photos because the bears slept almost all the time. So my date took a bunch of photos of me posing with the bear, no problem.

When it was his turn to enter the bear pen for me to take his photo, the koala opens its eyes and starts making a frightening sounds. And then all the bears started making those terrifying sounds, and they started bolting all over the place. The zookeeper literally starts screaming “GET OUT! GET OUT! GET OUT!” He literally threw my date back through the gate and screamed at us to freeze where we were and not to move. I was staring at the bears and if their massive freaking nails how they could rip us to shreds.

The zookeeper told us that in his entire decades-long career of working with koala bears, he had never ever seen them react to a human like that or ever moved that fast. Like, ever. And that there must have been something wrong with my date because koalas don’t hate anyone.I have photos of him posing with the bear and the bear like literally starting to freak out behind him.”

-- Amy and Evan, New Rochelle, NY

Worst First Date #4: “I nearly killed him”

“On our first date, I chose some weird martini with Chambord in it and it tasted like vomit. I felt horrible and had to lean my head on the wall. In the middle of the date, I announced I had to go and got in a cab and left. On our second date, I had just come from a reflexology appointment so I was all loopy and I ate all of his fries. Our third date, I nearly killed him by serving fish that had been in my refrigerator too long and had spoiled. He thought I was crazy. I kept calling him after at his office and he would tell his assistant to "take a message.”

Brooke and Neil, Petaluma, Calif.

Worst First Date #5: “My boyfriend had just ditched me”

“My boyfriend and I went away for the weekend to go snowboarding with friends (and friends of friends). On the first day, I did a faceplant in the snow and sprained my ankle. After getting back from the hospital, my boyfriend sort of ditched me to keep skiing. He made me feel like I ruined the trip on purpose.

My friend’s cousin Sid kept bringing me cocoa and Advil and tried to cheer me up. I was so cranky, it didn’t occur to me that this cute guy could have liked me. That night, while my boyfriend was getting drunk with his friends, Sid tried to play cards with me but I was so busy being furious and hurt because my boyfriend was ignoring me. The next morning, we broke up and Sid offered to give me a ride home. We got married a year later.

-- Ginny and Sid, Boston

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