Embarrassing Dating Moments – Part 2

Last week y’all heard about poor Megan’s almost-date where her tipsy, loose-lipped proud papa told a table of men that “she liked to pee in the woods!” It was a shining example of a date that should have come with a warning label.

The Triple D series is all about Disastrous Dating Don’ts. When I asked if any of you had embarrassing moments to share, several brave souls commented. The rest of those cowards just called me.

Below are my two favorite comments from last Friday’s post.

From Catie Rhodes:

I don’t really have any dating stories. I didn’t date a lot. I do have this story, though…

One night, this really weird dude wanted to take me riding in his car. So we’re cruising around. (Note: I grew up in a small town where that was all there was to do–other than get pregnant or smoke dope.) Turns out the dude has a PA system hooked up to his car.

As we pass women he finds attractive, dude gets on the PA system and says, “Hey, little girls.” When we pass a carload of jocks, he gets on the PA system and says, “Hey, sports dudes.” When we pass a carload of old ladies…you get the picture.

He did ask me to marry him that night. Since I was about fifteen, I refused. Ahh, the fun of growing up.

From Amber:

Sometimes the entire universe pulls together to give you a sign that you shouldn’t be dating someone.

Like the time I was having lunch with a guy and this conversation ensued:

“Jerry Springer is sitting behind you,” he said, motioning to a table over my shoulder.
“Very funny.”
“No, really.”
“I’m not turning around. I’m not falling for that.”
“Why would I lie? Why don’t you trust me?”

I turned to look over my shoulder. And there he was. Jerry Springer. Lunching at Friday’s. In a state nowhere near his studio.

“I can’t believe you don’t trust me.” He acted hurt the rest of the meal.

If Jerry Springer shows up on your date, TRUST me. It is an omen of much worse things to come.

From A Friend Who Refuses To Be Named:

As with Megan last week, some of my stories come via phone. Since I have a fairly rambunctious group of friends, I often have to change names to protect the not-so-innocent. We’ll call this woman “Jane.”

Jane was in a dry spell when this date happened. (For the uninitiated, “Dry Spell” means she hadn’t “gotten any” in a LONG time. If you know what I mean.)

She was a little excitable by the second date – she wasn’t seeing a love match, but she was seeing Mr. Get-Between-The-Sheets-RIGHT-NOW. So, in very uncharacteristic Jane fashion, she took this guy home and introduced him to her sheets.

When Jane got up to take a trip to the ladies room, she realized that she REALLY HAD TO GO. (As in, “not potty.”)

Jane’s guesthouse is a small cottage with big windows, and a single master bathroom back in the bedroom (the layout reminds me of a New York apartment). A fastidious girl, Jane just could not bring herself to GO with this man on the other side of that door.

[I was snorting with laughter by this point in her story. My comment was along the lines of: “So you can bring Mr. RIGHT NOW home and tear up your sheets with him, but you can’t go to the bathroom with him in your house??” Her response was: “Not like that!”]

No, our pal Jane grabbed some tissue, climbed out the bathroom window and ran across her backyard to GO behind a bush. Her place sits at the back of a large fenced property so she wasn’t super worried about privacy.

(Of course I asked why she even bothered hiding. Her answer? “I was naked.”)

In retrospect, what Jane should have worried about was security (or a robe). When she jumped down from the window ledge, it shut far enough to engage her window stop — that doohickey latch that keeps your window from opening more than two inches.

She said she has never in her entire life been more embarrassed than when she stood on her front porch naked, ringing her own doorbell. Eventually, her date came to the door and let her in. She got him dressed and gone in record time.

I couldn’t even FIND a good moral to this story (I was laughing too hard). If I’d heard from Jane before Megan, it’s pretty likely Jane would have claimed the #1 spot.

What about you – can you find me a great moral to Jane’s immoral story? Who gets Top Embarrassing Moment – Megan or Jane? If I use this story in a book, how do you recommend I change it (if at all)? And why is bathroom humor always so funny?

Last but not least, did you think of any more embarrassing dating stories for our Friday Fun here at More Cowbell?

About Jenny Hansen

Avid seeker of "more"...More words, more creativity, More Cowbell! An extrovert who's terribly fond of silliness. Founding blogger at Writers In The Storm (http://writersinthestormblog.com). Write on!
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9 Responses to Embarrassing Dating Moments – Part 2

  1. Laura Drake says:

    OMG, those rival mine! This one isn’t about my date, but a date of my sister’s I made memorable.

    My sister wasn’t due to show up with her new guy for a half hour. I looked over at my husband…he looked at me…you know THE look. He joined me in the bean bag chair, and – well, you know.

    My brain is in an estrogen fog, thoroughly enjoying the experience, and suddenly my husband is GONE. No, I mean I didn’t even realize he’d moved – he was just gone. I hear the bathroom door slam. I open my eyes to see my sister, standing in the doorway with her new guy.

    I am spead-eagled on the bean bag chair.

    Coming out of that bathroom after verbally beating up my husband was the hardest thing I’ve ever done, bar none.


  2. OMG! I laughed out loud over this story. I snorted.

    Back off, DEA. Air! I snorted only air.

    All of my “maintenance date” stories were intentionally targeted for search-and-destroy missions during happy hour sessions with Pinot and Grigio. I am now a staid, happily married, compliant, model citizen.



  3. Jane wins – hands down.


  4. Omigoodness! Can’t even imagine getting stuck naked on your own front porch…after intending to make like a bear in the woods. Whoah.


    • Jenny Hansen says:


      Not only would I probably not have been able to get out of the window, it is pretty likely that if I had tried such a crazy thing that God would have paid me back for that silliness.

      It would have been something like a ginormous gash on the hiney from the ledge or a rabid case of poison ivy from the bush. The universe just works that way. Hence, Jane and her front porch bell-ringing moment.

      That was the Big Person upstairs saying, “Jane, stop being such a jackass!”


  5. Jane’s story was funny! Maybe it’s her needing to get it soon rather than not going to the bathroom (they do share the same nerves). 😉


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