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Funny dating stories from both the ladies and the gents!

Michelle Douglas Chief Pattern Disruptor · 19 June 2024 · Leave a Comment

Hello, and welcome to another Wacky Wednesday, where we dive into funny dating and relationship stories. Or, perhaps, more accurately, dodgy stories. Today, I’ve got a collection of tales that will make you laugh, cringe, and maybe even gasp. Let’s get right into it!

The Jealous Ex

Our first story comes from a guy who met a girl on Tinder. She suggested a particular restaurant and insisted they sit at a specific table. Dinner went fine, but he wasn’t particularly interested in her. Things took a turn when she started getting texts from her ex. Turns out, she intentionally sat them in front of the tattoo shop where her ex worked to make him jealous. Yes, it sounds like a plot from a bad TV show, but it happened in real life!

The Life Insurance Pitch

Another gentleman met a woman through a dating app, and they decided to meet up for drinks. The conversation flowed well until the end of the date when she tried to sell him life insurance and pulled out some brochures. Talk about mixing business with pleasure!

The Cat Lady

This next story involves a guy who organized a movie date at a girl’s house. She had a two-person couch occupied by her cat. When he tried to move the cat, she stopped him, forcing him to sit on the floor. Thirty minutes in, he had enough and walked out. Not the most comfortable of dates, for sure, and I’m surprised he didn’t walk out immediately!

The Rapper with No Plan

A woman shared her date with a self-proclaimed musician in his thirties. He insisted on picking her up in his beat-up Honda (there’s the first mistake – never get into a car with a stranger!!!). At the restaurant, she discovered he lived with his ex, their child, and his parents, had no plans to move out, and boasted about cheating on his ex while she was pregnant. To top it off, his Tinder photos were ten years old, and he had several missing teeth. She texted her flatmate for an emergency rescue, claiming they were late for a party.

The Amway Surprise

One woman was excited about her date until she arrived at the restaurant and realized it was an Amway event. She thought she was in for a nice dinner, not a sales pitch.

The Feet Fetish

This last story highlights the importance of boundaries. A woman went on a date with a seemingly nice guy. During the date, she discovered his teeth were black, but she tried not to judge. After dinner, they went to a park, and he complimented her feet, then asked to massage them. Feeling unsafe, she reluctantly agreed but made an excuse to leave shortly after. He followed her, offering to escort her home, but she declined and decided to work on her boundary-setting skills before another date.


These stories serve as a reminder of the unpredictable and sometimes downright strange nature of dating. Whether it’s dealing with jealous exes, unexpected sales pitches, or uncomfortable situations, it’s all part of the adventure, and I would urge you to have a think about why this has happened in your reality.

Always trust your instincts, set clear boundaries, and remember to laugh along the way. See you next time!

Align With Love

Would you prefer to attract dates that you actually ENJOY? You can – once you align yourself vibrationally with having that in your reality!

To learn about how to do this, and so much more, check out the program!

Align With Love

And write your very own love story!

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Related posts:

  1. How to find true love without settling
  2. A tale of a date I went on over 20 years ago
  3. How to Manifest Love by Breaking Energetic Blocks Without Breaking Your Brain
  4. How to Get into Vibrational Alignment with Love (Without Accidentally Manifesting More Situationships)

Love & Relationships

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