10 Dating Stories That Made People Want to Swipe Left Forever

Relationships
3 hours ago

Dating can feel like a rollercoaster – thrilling in theory, but occasionally nauseating in practice. These 10 dating stories take awkward encounters to a whole new level, proving that love might not always be in the air, but disaster often is. After reading these, you might just want to delete your apps and invest in a good book instead!

1.

I went on a date with a girl I met in an online chatroom to see King Kong at the cinema. I was in my young teens and the ending absolutely shattered me, even though I knew it was coming. I cried. Not a lot, but a couple tears.

She noticed and asked incredulously if I was crying. I just nodded and without saying anything further she got up and left. Never returned any of my messages after that.

Oi_Kimchi / Reddit

2.

We’re joined by another couple, and we chit-chat with them. The woman hands her boyfriend a small gift bag. The guy opens the bag and finds a card with an ultrasound pic inside. The man is visibly upset and embarrassed, telling her that she knows he doesn’t want any kids.

A hushed argument ensues and the woman disappears into the bathroom. He tells us that he doesn’t even like this woman and really doesn’t want a kid with her. We finished our meals in awkward silence and often wonder what happened to those people.

tiredmommy13 / Reddit

3.

A guy pulls out a chair for a girl, she doesn’t realize what he’s doing, awkward pause. She sits down, the guy clears his throat and starts coughing because he cleared it too hard. She doesn’t know what to do, ignores him, picks up the menu.

Waiter comes, she asks her date if he knows what’s good, he says he’ll have what she’s having. She hands the menu to the waiter and orders seafood. Awkward pause, he’s allergic to seafood. He takes the menu back and says he’ll have a steak, the waiter leaves.

They sit staring, not quietly looking around or at their phones, staring at each other in silence until the food comes which they eat in silence. My girlfriend and I were on the edge of our seats waiting for something to happen.

THATsyracusefan / Reddit

4.

High school. My awkward phase. My mother tells me I’m pretty, and I finally get up the courage to ask out the cutest guy in my year to the movies. He says, “I’ll have to think about it” and takes my phone number, which I thought was a good sign.

We texted a few times, arranged a meet-up at the movies. Gets to the day, I’m getting ready to go, make myself look all pretty and do my hair nice. I get to the movies. He’s there, but so are all his friends.

All of them including the guy I liked are laughing at the absurdity that he could ever want to go out with me, laughing at the fact I got dressed up. It was all a big prank. I’ve never been so humiliated.

Madeleine227 / Reddit

5.

“Oh, you are too early! You see, I really want to go out with X and I decided that if he hadn’t asked me out by next Friday, I’d settle for you, so could you please ask me next Saturday? Because then I’ll know if I have to or not.”

This was not Junior High or High School. I was 32, she was 30, both of us divorced with children.

KYHY / Reddit

6.

I’d just checked in an older woman, possibly in her early 60s/late 50s, with a young man who couldn’t have been older than 25. Midway through their meal, I went to check up on them, asking, “Aw, are you taking Mom out today?” They both turned with straight faces and the young man said, “She’s my girlfriend.” I whispered an apology and just peeled myself away.

***saidwhuttt / Reddit

7.

I work in a restaurant where we make our own ketchup, and some people don’t like it. Fine, whatever, if you’re nice I’ll bring you the secret Heinz ketchup as long as you don’t tell anyone. Anyway, a woman is seated at my table looking super excited and tells me she’s on a blind date.

This dude shows up on his phone, ignores my hostess, and eventually finds the woman waiting for him. He kept talking on his phone for 15 minutes, and when he finally hung up, I went to the table. He tried to order for her, which embarrassed her, and for himself ordered a well-done steak and fries.

When I brought it to him, he asked for A1 and real ketchup. When I informed him we had neither, he grunted and said he had ketchup packets in his truck. As soon as he walked out the door, she asked for her half of the check and her food to go. I helped her leave out the side door before he could even come back. It was awkward serving him after that. He used 7 ketchup packets.

TheDoubtfulGuest / Reddit

8.

The date was going very well. We met at my work in a video store, bumped into her a couple times, and then saw her while doing laundry. We talked for a couple hours, then went to my place. At some point, I realized that I’d forgotten her unique version of a common name.

I knew I’d get it wrong and it would be obvious. I snuck into my roommates room, woke him up, and asked him to walk out like he didn’t know she was there, so that he could act embarrassed and introduce himself before I “had a chance”.

Unknown author / Reddit

9.

On a first date with a girl, we decide to just drive around after dinner. We had a great time exploring and found this creepy road back in the woods that was closed, and I decided I wanted to be a rebel and go around the barriers, but she got a little freaked out and objected.

That’s when I realized, from her perspective, some guy had picked her up and took her back in the woods in the middle of nowhere on the first date. Unintended, creepy as hell, but had a second date!

midget9 / Reddit

10.

In 10th grade for prom, I did a big romantic ask involving our school’s marquee (the big signs with interchangeable letters outside some schools) and she said yes. However, the night came, I picked her up, she refused to take pictures with me, and barely ate her dinner.

Turns out she’d used me just to get a ride to prom (on the outskirts of Houston, around an hour away) because she didn’t have a car and her actual date lived out where the prom was and didn’t want to drive into town to pick her up. Literally, the second we walk inside, she runs away and jumps into the other guy’s arms.

Archany / Reddit

You know a date’s in trouble when even the waiter can see the sparks are fizzling, long before the breadbasket arrives. In this article, waiters became the unintentional audience to romances crashing and burning before they even took off. If you’ve ever had a painfully awkward first date, these tales might just make yours feel like a love story in comparison!

Preview photo credit tiredmommy13 / Reddit

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