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How to Ruin Your Own First Date

How to Ruin Your Own First Date

5min to read

There are two truths about dating that everyone needs to be aware of:

  1. There are so many ways to mess up a first date, and
  2. Sometimes you’ll be the one who messes it up.

That’s why it’s important to own up to our mistakes – just as some of these Reddit users did as they recounted their worst first dates… that were entirely their own fault.

1. Ruin your date for just $20!

“I offered to pay for the bill.. she insisted to pay half. Didn't fight it, but only had a large bill so I pocketed her money and put my bill in. Anyway long story short I did the math wrong and stole 20 bucks from her. She sarcastically said “thank you” and I thought she was being sincere..”


2. Unsuccessful sweet talk

“We order a small snack for our coffee and as it’s arriving at the table he pulls out his Nokia phone. Trying to make a lighthearted joke I say ‘MAN that has got to be the oldest phone I’ve seen in a while’. I really dug it in, trying to break that friendly wall. Well. Turns out it’s not a Nokia. It was his insulin pump.”


Guess he wasn’t as insulin-to it as she was.

3. A hair-brained date

“I wore a wig for a few months after shaving my head for charity. Went to the bathroom, took it off to straighten it and then walked out without putting it back on.


It’s all fun and games until your wig gets snatched. 

4. Ménage à trois-cious

I didn’t know it was a date and brought my (very new) girlfriend to the movies with us.”


Clarifying whether or not it’s a date is always less embarrassing than this.

5. (Not-so) Mixed signals

“She invited me up to her place, got us each a glass of wine and then took her pants off, at which point I assumed she was going to bed, said goodnight and left.”


When you assume, it makes an ass out of u and me. 

6. A date by any other name…

“I asked his name in the middle of the date.”


Side note: If you need to do this, use one of our brilliant excuses, such as “I’m writing out our wedding invitations” or “I’m assigning you as my next as kin”. Both totally appropriate for a first date. 

7. A blessed date 

“I sneezed just as we were about to kiss.”


It’s snot what his date was hoping for.

8. A quick cash grab 

“For me, It was getting my bank card swallowed by the ATM just before meeting the girl, then awkwardly explaining that I’m not a cheapskate and this has never happened to me, followed by let’s grab a cab to my house so I can borrow money from my mum….I never saw her again.”


Thank goodness for Apple Pay in 2019. 

The silver lining of each of these stories is that the Reddit users had the self-awareness to recognise their own mistakes. Hopefully, they also managed to scrub away some of your own bad first date memories…

Rejig your love life.

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