23 Real Men and Women Share Their Best and Worst First Dates

My now-husband and I met through friends during our junior year of college, and after hanging out with the group a few times, he asked me to go to dinner one night. I remember being really, really nervous and picking out at least five different outfit options with my roommates before putting on a fashion show and finally settling on one. There were all these butterflies, and about an hour before Radley was supposed to come pick me up, he texted me, saying, "Warning: I accidentally buzzed a bald spot in my hair." It was hilarious, and when he picked me up, he was so shy and sweet about the whole thing. I found it pretty adorable, and the giant, four-inch-by-two-inch bald spot on the top of his head totally broke the ice. Four years later, we were married, and we've been together six years now. Oh, and for the record, he hasn't buzzed his hair since.

This photo is from about a week after our first date. Not pictured: the bald spot.

One time, my date showed up for our first date with two wrapped presents. In the likely case that you've never received wrapped presents from a practical stranger, let me tell you: it's a little uncomfortable. The first was a bottle of wine and an opener, which was reasonable and appreciated because the restaurant was BYOB. But, as he opened the bottle he proceeded to tell me he didn't like wine and I'd have to drink it myself. The second package had a red rose tucked in it and revealed an inch-thick, stapled printout of Oprah's online guide to starting a book club "because every woman loves Oprah, right?" Cue long sexist rant about things women like. Every moment that followed felt like an SNL sketch. I guzzled wine while I learned the man's spirit animal is a half lion, half turtle, and someday, when he's in better shape, he's going to get a tattoo across his stomach and chest. He did not receive my final rose.

My first OKCupid date is probably to this day the worst date I've ever been on. I had the guy meet me two doors down from the bar I was working at in case it went terribly/he was a total freak. He showed up to the moderately nice restaurant in a t-shirt and baggy jean shorts, was about three inches shorter than his profile claimed he was, and didn't make eye contact with me the entire time, choosing instead to play with the candle on our table. To make matters worse, there was an issue with our food, and mine came out 20 minutes before his did. The whole date was so awkward and awful that I literally jumped into a cab to get away from him at the end of the night, had it drive me around the block, and then went to the bar to drink away the anguish with my co-workers.

I should preface this by saying we eventually broke up, but I'll always remember my first date with my ex. We were hanging out with a bunch of mutual friends and he kept staring at me, so I asked him why. He hesitated, then confessed, "I'm staring at you because I think you're pretty." No one had ever been that up-front with me before, and I was totally done in. We split off from the group and went to dinner alone. It was two weeks before Valentine's Day, and the restaurant was decked out in holiday decorations. It was awkward and perfect at once, and by the time we left the restaurant, it had begun to snow. He literally dipped me and kissed me on a snowy New York street corner. It was probably the closest to Sex and the City I've ever been.

Mike and I met at a grocery store for our first date so that we could get food to make dinner together. We walked around the store, and I don't think he ever stopped talking. (I later learned that this is how he always is.) We couldn't settle on anything to have for dinner, so we just got ice cream. But then when we were waiting in line to check out, he said to me, "Someone once told me that if two people have the same color eyes, they're a match made in heaven." I, of course, asked him what color my eyes were, and he said, "Same color as mine — I guess we're a match!" It was almost three years ago that I fell for that cheesy line, and now we're engaged!

I was in high school and had met a guy briefly before we decided to go to Magic Mountain for our first date. Worst. Idea. Ever. He was superloud and obnoxious and yelled at the ride workers when his seat belt was too tight. Lucky me had to spend the entire day with him. Obviously we couldn't go to a bar or anything, but I should've stuck to ice cream or something that offered an easy exit for a date gone bad. Lesson learned.

UPDATE: Lisette just spotted her not-so-magical date on the The Millionaire Matchmaker as yes, the millionaire.

One of my most memorable dates was in high school. I went on a double date with a girl Kristen, and we set up my friend Keith with her friend Karen. Dinner was at the Rainforest Cafe, and the girls ordered salads. Karen was trying a new salad and ate about half of it until she realized it wasn't exactly to her liking. We asked if she wanted something else or part of our meals. She said, "No, that's OK, I've done this before, I'll have it taken off the menu." Karen proceeds to pick up a large forkful of salad, plucks a long hair off the top of her head, and wraps it around the salad on her fork. "Waiter, waiter, there is hair in my salad!" Karen yelled across the restaurant. Not only did they take her meal off the check, but we didn't pay for any of our meals that night. Now it may sound like Karen was the crazy one, but two weeks later I ended up dating Karen and not her friend, Kristen, my original date for the evening. 

I spent the Summer going into my senior year of college studying in Rome. Abroad with my best girlfriend, we spent the days in museums and the nights in bars. On our second night out, we got picked up by a cute pack of Italian boys. We paired off, and I spent the night using my broken Italian and figuring out his fractured English. After a few fun nights out, I decided he was more trouble than he was worth, so Stefano and I "broke up."

My BFF still continued to see her guy, and at the end of our time in Rome, he offered to drive us to the airport. Awkward, my "ex" was in the backseat to accompany us to the airport. (This took place when you could still wait at the terminal with loved ones at the airport.) We all waited for our flight, looking at magazines and books in the terminal gift shop. Sarah and I were on one side of the shop, Stefano and Daniele on the other side. This is when I noticed that Stefano was holding a magazine up VERY close to his face sort of examining/reading? I turned to Sarah and said, "Don't you think it's a little strange how close Stefano is holding that magazine?" My question was received with uncontrollable laughter, like I was not in on the joke. "Heather, soo, yeah — Stefano, is blind. Not like blind blind, but like can't see out of his left eye and can only make shapes out in his right eye." Yeah . . . so the blind guy wanted to date me.

So I met this guy on Halloween. I don't remember what he was dressed as, but I was in a full '70s-inspired ski suit, like something Farrah Fawcett would have worn if she was on the slopes. After a few drinks I agreed to a date with him. I don't know how to say, "No, I'm not interested." He was a very nice guy, very, very nice guy. Supersweet. I just wasn't ready for any sort of commitment. So then he called me the next morning and was like, "Can't wait to see you." We were texting, making plans for the date all day, and then I was just thinking I can't do this. But instead of saying I can't make it, I said my aunt died and that I had to fly home to Kentucky. He was very caught off guard.

A couple years later we reconnected on Facebook — I don't know why — and I agreed to meet him for a drink. And he said, you know when you said your aunt died I didn't believe you and thought you were trying to get out of the date. And I was like, "No, she did die. It was horrible." I just pray to god that nothing will happen to my real aunt thanks to my lie.

If you're single and own an iPhone, you've likely downloaded Tinder — who hasn't? Is it for everyone? No. Was it for me? Nope, but there was one exception. From the start, I was inundated with messages that ranged from extremely cheesy to overtly obnoxious. So, when I noticed a simple, "Hi, Katie!" it was refreshing. Debating over the perfect reply I responded with, "Hi!"

Adorable texts were traded back and forth for a few months. Yes, months. I would occasionally tell friends about the "Tinder guy" and they would all reply, "Wait you still haven't gone out?" Me: "Ummmm . . . no." After two months, a close friend got wind of "Tinder guy" and pulled me aside to set me straight. His advice: be aggressive. Me, aggressive?! Fine, what do I have to lose? Guess what: it worked. We set a date.

But now there's a problem: after three months of texting, what do we talk about on our first date? We'd already covered the basics: work, family, and Miley Cyrus. Cut to the day of the date. We decide to meet up for drinks . . . at his house. Editorial note: don't do this. In hindsight I realize the entire scenario screams murder. What in the world would we talk about in person, face-to-face? Duh, Katie, the same things you text about. I was really overthinking it. Conclusion: it was the easiest date ever. If you've already exchanged emojis with someone, sharing a bottle of wine should be a breeze. Or you could just make out for a few hours and avoid talking . . . that happened, too.