...and what they learned from it.
If you’re anything like me, when it comes to dating, it’s a love/hate. At first, you could be super excited about somebody, whether you meet at a party or on an app. But, when it comes to actually going on a date with them, you two may not click the same way. Suddenly, you go from having high expectations to being on the worst date you’ve ever had. But, of course, we learn from every experience, both the good ones as well as the bad ones.
We decided to ask women about their worst dates — and what they learned from them. Perhaps you’ll be able to relate (but hopefully not!).
#1 He Asked Me To Help His Music Career -Kiedra, 33
“Worst date ever! I meet this guy at the movies, because I don’t believe in letting strangers know where I live. He told me he ordered the tickets in advance. When we got to the movies, the manager came out and said the tickets were purchased with a stolen credit card, and the owner of the card called and said they didn’t make the purchase. My date told me he had his cousin buy the tickets and was embarrassed, then just repurchased the tickets. We watched the movie and didn’t really talk or interact during the movie. After the movie, he told me he wanted me to hear something in his car. I was a little hesitant to get in a stranger’s car, especially after the card drama, but, reluctantly, I proceeded. Once inside this man’s car, he played me a mixtape of his own music and asked me for help with his music career.
From this experience, I learned not to disclose what I do for a living until a few dates in to make sure they like me for me — and not what they think I can do for them.”
#2 He Wouldn't Get Out Of The Car -Karina, 40
“Gosh, I had so many bad dates! One of the worst dates was that it was a blind date. I knew he was driving a Mercedes and walked out of my apartment building and saw two Mercedes vehicles, one in front and the other across the street. So, naturally, I got into the one in front, but it turned out to be a woman driver. I was obviously embarrassed about getting into the wrong car.
What I learned is, when going out with anyone, look for the person that makes an effort. The guy above clearly did not care to get out of the car and greet me outside, which would make him a bad long-term partner. NEXT! I still went out with him, but I was mad and made him bring me back five minutes later.”
#3 A Few Missing Details - Bonnie, then-24
“I’m a celebrity matchmaker and relationship expert. When I was 24, I was set up by my godmother, who had a friend whose nephew was in ‘show business.’ Being in L.A., I was excited to meet this celebrity who was single and supposedly handsome. We spoke and he said he would pick me up for a two-hour ride up the Pacific Coast Highway, along with some other couples, and then we’d go to an upscale brunch at a ritzy hotel. Imagine my surprise when I answered the door and there he stood head-to-toe in fringed leather with a red bandana across his forehead. He looked at me in my mini dress and said, ‘Come with me.’ I looked to the street, where I saw his Harley-Davidson Fat Boy motorcycle, along with four other couples on their motorcycles. It was a hot July 4th day and the bike kept overheating, so we had to keep pulling over to the side of the freeway for it to cool off. So what was supposed to have been a two-hour ride up the highway along the Pacific Ocean turned into a nightmare experience. Worst date ever!!!!
What I learned was, even though he wasn’t for me because of our different lifestyles, I set him up with a friend of mine and they had a healthy relationship. Lesson learned: ‘There is a lid for every pot.’”
#4 He Gave Me The Creeps - Malia, 23
“Here is my worst date (so far): I was at a Halloween party and a guy approached me and asked for my number. We texted a little over the next week and I agreed to go out with him. He told me we would eat dinner and do an activity. On the night of the date, he picked me up from my apartment and took me to his place, which was in the basement of an older home. I was confused, but assumed we would probably be making dinner or something there. After entering the house, he took me to a back room, where the lights were dimmed and he had lit candles scattered around the room. His guitar was sitting next to the couch and he told me we would be composing a song together (I don’t sing… what happened to dinner?) and that his roommates had left to give us some privacy (creepy). Thus began about half an hour of awkward song composition.
About three verses into the weirdest song ever written and without warning, he turned to me and asked if I was ticklish (what??). I began to panic and said in my most serious voice, ‘No, I am not ticklish at all’ (which was a total lie, because I am extremely ticklish). He began reaching for me (red flag #423), so I jumped up from the couch and ran to the other side of the coffee table. He jumped off the couch with a big grin and started coming toward me. I ran around the coffee table with him chasing me a couple times before I screamed ‘STOP!’ and ran out the door, up the stairs, and out of his house. A mutual friend informed me that he got married several months after that to a girl he had taken to a Halloween party... Hmm.
Two major lessons from this experience: 1) Meet your first dates in public places. 2) If you are uncomfortable with the situation AT ALL, you have every right to leave, even if it means you leave two minutes into your date. You don’t owe anyone your time, and you don’t have to be nice, because your safety is more important than anything else.”
#5 Three's A Crowd - Emily, 28
“The worst date I’ve ever had was when a guy made me meet him at his apartment, where he smoked weed and watched cartoons before we went to a restaurant closer to my place. He only talked about himself and, about 10 minutes into the date at the restaurant, two of his friends sat down at our table and ate with us. They all talked about DJing and didn’t ask me a single question.
What I learned: I was so caught up in making a good first impression that I didn’t push back on anything the guy did. The first impression is important, but not if you’re the only one trying. Secondly, I learned that it’s nice to have an out. If I had said I would meet him at the restaurant, I would have avoided the whole thing at his apartment and could’ve easily left the date when his friends joined.”
#6 We Had Nothing In Common - Jenn, 23
“I decided to take a risk and DM this guy that was fairly popular around town… surprisingly enough, he answered, we talked for a bit, and he asked me out! So how did the date go? Well, uhm, okay let me try to explain... 1) He wore flip-flops: No. Just no. Like, are you kidding me?! He is a lot older than me and he’s shlummin’ around in f*&(ing flip flops??!! 2) He didn’t pay for me: This is the second time this has happened to me. I spent $8. He spent $30 and he couldn’t pay for my $8 meal?! OUTRAGEOUS. STILL SHOOK. 3) He was funny, but we had no common interests: He was super cool, super laid-back, and so nice… butttt, besides the mutual ‘friend’ we had, we didn’t really have much in common. And, after seeing how he was dressed, I really knew things would probably not work out — lol (I promise I’m not shallow!).
The moral of my super embarrassing story is that taking risks can lead to bad experiences, but the bad experiences are what teach you what not to do next time. I learned that just because someone may be popular doesn’t mean they’re going to be a good person for you.”
#7 He Surprised Me With Kids - Alexa, 37
“It’s hard to choose just one date as the worst, but this one was pretty bad. Not only was my date 45 (!) minutes late — we were meeting in a public place since we’d ‘met’ online — but then he proceeded to tell me why he was late: He had to drop his kids off with his ex. What?! As a rule, I don’t date people with kids (sorry), since I don’t want any, and he couldn’t have said this in any of our message exchanges?! Then he wants to go to ‘a nice place for dinner,’ which ends up being a fast food pizza stand where you get slices to go! We had to order, pay, then wait, and when the cashier said, ‘Together or separate?’ he said, ‘Separate.’ I was seething. I said, ‘Yeah, separate,’ and took my pizza to go — without him.
I learned that when someone starts out being disrespectful — 45 minutes late!! — things will probably go downhill from there, so pay attention to all the little things; they’re really big things in disguise about the person’s character!”
#8 He Told Me He Missed His Ex -Courtney, 38
“When I was around 30, I’d just gone through a bad breakup and decided to finally go out with a guy friend, ‘Mike,’ who’d bugged me for years to date him if I was ever single. He took me to a fancy place (cloth napkins!), but then talked about how much he missed his ex — ‘we may get back together.’ I should have asked him what he was doing out with me then, but my self-esteem was sooooo low from my break-up, I didn’t even care much. We went back to his place — you know what that means, and, TBH, I needed some rebound sex… but then he put on a documentary film he’d produced and wanted my thoughts. What?! This was L.A., but here this guy finally got me home and he wants notes on his film?! Plus, I was exhausted from all the wine we’d had at dinner, but fine… so we spent over two hours watching this film, with him pausing every few minutes to ask for my thoughts and write them down!!!
What did I learn? That I’m not a rebound person, and I’ve also since learned the importance of self-respect: I should have left the date right after he said he wanted his ex back (or right after dessert!).”
#9. He Rated Me -Katie, 36
“This guy took me to a minor-league hockey game (I don’t even like sports!), we had to stand at the back of the arena (he didn’t want to pay for tickets!), he wanted to split nachos (which are really hard to eat while standing!), and he spent the whole date talking about a rating system he has for dates (he said I was scoring at seven or eight). This was at the end of January during my freshman year of college. On the way home, he said we should plan our next date for Valentine’s Day, but I told him I already made other plans (I hadn’t!).
The lesson? This forced me to have to find another Valentine’s date so that I wouldn’t have to go out with that lame-o again. The guy I found instead? We’ve been married now for 13 years, have traveled the world together, and have a beautiful daughter. And when we go to the very rare, occasional sporting event? We always get the VIP seats.”