May 24, 2022

4 Hilarious Dating Fails—& what they taught me about Kindness.

Friday night on a long weekend, I find myself researching how to make chocolate croissants.

I may never attempt them now that I know; however, having learned that the whole process is complicated, I will never take another croissant for granted—especially the chocolate, gooey ones.

My home has become a writing and art den, and single living has its perks, yet I still wonder about partnership.

What do I wonder you might ask? I half jokingly wonder if learning how to make French baking will bring a good man. They say, after all, the way to a man’s heart is through his stomach, which is possibly the second heart on top of being the second brain anyway.

This leads me back to the effort involved in actually putting myself out there. Although I do not feel ready, I am mentally preparing for the day that I will try again…

Because as far as dating goes, I am hot mess and there have been so many dating fails. If you need a laugh please read on and learn from my mistakes.

Dating in the modern world can be a challenging task.

The various ways we meet people have expanded and yet the traditional date still stands as the best way to get to know someone. There are many suitable places and things to do for first dates or dates in general. My word of caution here is to be mindful who you arrive with and who you leave with. Try to be present and aware of yourself and others.

Here we go:

1. Several years back, I had a sweet Jack Russel Terrier who thought he was human.

He came with me everywhere, and this included dates. One summer night, I waited to be picked up and jumped into a vehicle which I thought belonged to my date, only to find a complete stranger. My dog figured this out before I did and he was so scared he lost control of his bladder. After several apologies and offering to clean the young man’s car, I cautiously exited the vehicle.

He said as I was leaving, “It is great to meet you—and you have the sweetest dog.” I sighed and smiled again, apologizing profusely. The lesson here is to be mindful of the car you are getting into. Another lesson is that we meet great people along the way—even in non-dating situations. Dogs provide a great way to meet people!

2. Another unskillful dating fiasco was set in a darkened upscale restaurant.

I was feeling a little on edge and nervous, and after a trip to the bathroom for some mirror self-talk, I returned to sit down at the wrong table.

The man I sat down with was also surprised, yet he listened as I placed my napkin in my lap and began to babble on. I was surprised when I felt a tap on my shoulder and my actual date asked if I was going to return to join him or finish the rest of the night with the stranger. My face turned a bright shade of crimson. Gratefully, my mistake helped release the tension between us, and what followed was laughter and an enjoyable evening.

3. Fast-forward a few years—in a movie theatre, I grabbed the wrong man’s hand during a frightening scene. 

I didn’t realize it until my date looked over at me, puzzled, and then had a good laugh. The stranger, however, said nothing and let me hold on for dear life. Human beings are generally compassionate and kind.

4. My last and final fail I will share is the time I went on a dating hiking tour.

After using the washroom, I returned to a guided tour with my dress tucked nicely into my underpants. While touring and sightseeing, it wasn’t my date who noticed my undies, but a complete stranger and a gaggle of older women who had the best laughs of their lives.


I could go on and on forever. I dread first dates, but unfortunately, there is no other way to get to know someone. Even though I would like to fast-track through it all, I know there is no other way. So I am preparing, although I sincerely ask: can we really prepare?

I can proudly say, however, that I am ready to put my dating woes and fails to rest. At this life stage, I know who I am and what I want and need. If mishaps happen, I will laugh—for isn’t dating supposed to be fun?

We can often get consumed and overthink everything, scrutinizing and studying our romantic interactions, and yet this rarely helps us in the end.

What I have learned from my mishaps is we are human, and we have to put ourselves out there in order to get to know people. We are not alone in our mishaps, and everyone is nervous and excited during those preliminary encounters.

I might never feel ready—so maybe it is time to just begin.

Read 13 Comments and Reply

Read 13 comments and reply

Top Contributors Latest

Renee Fesser  |  Contribution: 67,215

author: Renee Fesser

Image: Shiebi AL/Unsplash

Editor: Catherine Monkman

Relephant Reads:

See relevant Elephant Video