7 People Share Their Worst First Date Stories (& It’s Pretty Bad)

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Silas & Grace

An unhappy woman on a date.

I’m gonna be honest, while I haven’t been on any bad first dates, I still get (a bit too much) enjoyment out of reading other people’s stories.

It’s entertaining, share-worthy, and a good reminder that sometimes it’s ok to not go on a date because you feel bad for someone and just pass.

Also, if you need some time to just relax with a cup of coffee and read about other people’s shocking stories, then no judgment, that’s why I made this list.

So take a few minutes, be happy that people are more than comfortable with sharing their (cringe) experiences, and enjoy yourself.

Side Note: Using stock photos for this made these stories so much funnier for me.

1. (Apparently) Not Enough Money

A woman stealing a sleeping man's wallet.
PHOTO CREDIT: EVERETT COLLECTION/SHUTTERSTOCK

“Had a girl try to convince me to cut off my long hair for the date. The first date. She knew I had long hair, it wasn’t a blind date. She also brought her dog unannounced, insisted it go into the bar with her, then only talked about money for the next hour or two, constantly pestering me about how much I made. The second I caved in the date was over. Ms. Moneybags still let me pay the tab.”— Unknown

2. How Dare You Not Know as Much as Me?

A man looking judgingly at his date.
PHOTO CREDIT: FIZKES/SHUTTERSTOCK

Date: Brother-in-law’s brother

“It was at his company’s Christmas party. While on the date, he tried to make conversation with me about photography – something we both liked – but wanted to talk super-technically about equipment.

He became irritated when I didn’t know anything about my camera or lenses, etc. He proceeded to get drunk and belligerent and kept loudly talking about the fact that I wasn’t having a good time. We obviously never went out again, but he was family, so I got to see him a lot. He’d always just hyperventilate when I came into a room.” — margaretb49238f5cc

3. Bringing Your Brother Seems Like a Valid Move

A wallet on a table.
PHOTO CREDIT: KANOWA/SHUTTERSTOCK

“One girl brought her brother along and they stole my roommates pay check off my living room table.”— Unknown

4. Recycling is an Unforgivable Sin

A woman looking away from a man and being unhappy.
PHOTO CREDIT: JUST LIFE/SHUTTERSTOCK

“My favorite one was I picked up this girl and she gets in the car and before even saying hello or anything. she asks me:

“Do you recycle?”

and i’m so blown back by this question, and pause for a second:

“of course who doesn’t recycle?”

and she just says:

“we’re not gonna get along.”

should have kicked her out of the car lol.”

Unknown

5. It Was Her Loss

A toothbrush on a marble surface.
PHOTO CREDIT: ANNA PUZATYKH/SHUTTERSTOCK

“I was talking to someone online once who went on about having bad oral hygiene. I was totally turned off but tried to be polite and said he should set alarms for reminders, he said it didn’t work and needed someone to remind him.

He also said he had such bad social anxiety that he needed someone to make doctors appointments for him. That’s valid, but it wasn’t what I was after in a romantic relationship. I politely told him it wouldn’t work but thank you. He literally told me it was my loss. 😂” — simplysarahish  

6. Concerning Food Choices

A woman angrily staring at a date.
PHOTO CREDIT: FIZKES/SHUTTERSTOCK

“I was seeing a food editor for a while, and to be fair, at the start he was really lovely. Engaging, interesting, funny; all that good stuff.

That said, you know how when a chef comes home from work, often the last thing they want to do is cook? Well, I’m guessing he had that, but for eating good food. Because when I tell you that every time he chose a place to eat, I developed a new food phobia, I mean it.

His work took him to loads of fancy dinners and Michelin-starred restaurants, so I understand if he’s sick of THAT (take me to an old-fashioned caff or run-down local gem of a restaurant any day). I’m not fussy at all, and I love stuff like chicken livers and pickled cherries. In other words, it’s not a money thing or an ‘unadventurous date’ thing; he just had a truly shocking palette.

His culinary offerings included: undercooked pub cocktail sausages inexplicably coated in honey, a bowl of genuinely inedible bacon-flavoured corn puffs, and unsalted bread that was still a gummy ball in the middle. It was meant to be a San Fran-style sourdough loaf.

It turned out he wasn’t particularly into me and had been seeing someone else the whole time, so maybe I should have taken the horrible food as the hints they probably were. Just remember, ladies — a pack of mini pickled onion-flavour cured sausages is not likely to come from someone who cares about you.” — aglover  

7. Cheating + Cops Called

Woman sadly sitting at a table.
PHOTO CREDIT: TWINSTERPHOTO/SHUTTERSTOCK

“Good date. Having fun. Good conversation. Enjoying the nice spring weather on the porch of a Mexican restaurant. We have just asked for the check and then a woman shows up and threw her keys at his face. He pretended it didn’t happen. It comes out (pretty quickly) that this was his girlfriend. They get into a right proper fight in the parking lot and the cops show up.

I can’t leave because my card is inside with the server and it’s taking 1000 years.” — mophilda  

49+ First Date Questions to Help Kill Long Silences

Couple hanging out with each other.

If you’re planning (or want) to go on a date and you wanna make a good first impression, then you’re gonna love these topic ideas.

And I think you’ll especially like them if you hate awkward silences.

Read More: 49+ First Date Questions to Help Kill Long Silences

102 Conversation Topics You’ll (Actually) Wanna Use

Women at a cafe hanging out.

Long silences and not knowing what to talk about next are kind of the worst when you want to be more outgoing.

But no more!

I’ve got over 100 ideas you’ll actually wanna try.

Read More: 102 Conversation Topics You’ll (Actually) Wanna Use

19 (Truly) Helpful Ways to Make Friends as an Adult

Two women talking in a cafe.
PHOTO CREDIT: MONKEY BUSINESS IMAGES/SHUTTERSTOCK

Making friends as an adult can be hard, but it doesn’t have to be.

No really, I created a list of tried and tested and workable ways to make good friends.

You’ve got this!

Read More: 19 (Truly) Helpful Ways to Make Friends as an Adult

Chasing Foxes was started in 2016 as a way for Grace and her husband, Silas, to start traveling. However, they started to realize that they had a passion for improving themselves, and wanted to help others level up their lives as well. So whether it's with cooking, travel, or staying healthy, they want to help you better your life bit by bit, as they do the same.

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Silas & Grace

Chasing Foxes was started in 2016 as a way for Grace and her husband, Silas, to start traveling. However, they started to realize that they had a passion for improving themselves, and wanted to help others level up their lives as well. So whether it's with cooking, travel, or staying healthy, they want to help you better your life bit by bit, as they do the same.

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