Most Embarrassing First Date

Since we were on the subject of “Nuts and Dates” in yesterday’s post, I wanted to share this one with you. Since it’s from “The Tonight Show With Jay Leno” you may have already seen this. If you haven’t, please read and enjoy.

Jay Leno went into the audience to find the most embarrassing first date that a woman ever had. The winner described her worst first date experience. There was absolutely no question as to why her tale took the prize!

She said it was midwinter… Snowing and quite cold… And the guy had taken her skiing in the mountains outside Salt Lake City, Utah . It was a day trip (no overnight). They were strangers, after all, and had never met before. The outing was fun but relatively uneventful until they were headed home late that afternoon.

They were driving back down the mountain, when she gradually began to realize that she should not have had that extra latte. They were about an hour away from anywhere with a rest room and in the middle of nowhere! Her companion suggested she try to hold it, which she did for a while.

Unfortunately, because of the heavy snow and slow going, there came a point where she told him that he had better stop and let her go beside the road, or it would be the front seat of his car.

They stopped and she quickly crawled out beside the car, yanked her pants down and started. In the deep snow she didn’t have good footing, so she let her butt rest against the rear fender to steady herself.

Her companion stood on the side of the car watching for traffic and indeed was a real gentleman and refrained from peeking. All she could think about was the relief she felt despite the rather embarrassing nature of the situation.

Upon finishing however, she soon became aware of another sensation. As she bent to pull up her pants, the young lady discovered her buttocks were firmly glued against the car’s fender. Thoughts of tongues frozen to poles immediately came to mind as she attempted to disengage her flesh from the icy metal. It was quickly apparent that she had a brand new problem, due to the extreme cold.

Horrified by her plight and yet aware of the humor of the moment, she answered her date’s concerns about ‘what is taking so long’ with a reply that indeed, she was ‘freezing her butt off’ and in need of some assistance!

He came around the car as she tried to cover herself with her sweater and then, as she looked imploringly into his eyes, he burst out laughing. She too, got the giggles and when they finally managed to compose themselves, they assessed her dilemma.

Obviously, as hysterical as the situation was, they also were faced with a real problem. Both agreed it would take something hot to free her chilly cheeks from the grip of the icy metal.

Thinking about what had gotten her into the predicament in the first place, both quickly realized that there was only one way to get her free.

So, as she looked the other way, her first-time date proceeded to unzip his pants and pee her butt off the fender.

As the audience screamed in laughter, she took the Tonight Show prize hands down.

Or perhaps that should be ‘pants down.’ And you thought your first date was embarrassing!

Jay Leno’s comment… “This gives a whole new meaning to being pissed off.”

Oh, and how did the first date turn out? He became her husband and was sitting next to her on the Leno show.


You can’t help but wonder if after such a bonding (and unbonding) first intimate experience together, whether a “golden shower” became a favorite part of their foreplay, leading to love making. Or if not regularly, then at least on their anniversary! “Honey, don’t send me no flowers, just give my ass that golden shower!”

But that would have never happened if it was me in that situation. Not because I wouldn’t do it, but because I always keep a can of WD-40 in my car. It’s an excellent lubricant, and sometimes it’s the only thing that works when you really need to free up something that’s frozen. Like frozen nuts, bolts and uhh, even butt cheeks!


WD-40 can free up just about anything.

Okay, so I guess we now know that it’s not the only thing that works for frozen butt cheeks. Lol ;-) But now under those circumstances, which “solution” would you prefer? Lol

Yes folks, the story on Leno of how that couple first met, is a true story. It’s all part of this peculiar phenomena we have in this day and age, where lots of people are saying “Please! Please!! PLEASE!!! I wanna be next! Please let ME be the next one to totally humiliate myself in front of a mass audience! Because I’ll do ANYTHING to get on TV!!!”

It’s almost like a kind of mass exhibitionistic masochism that so many can’t resist. They’ll do just about anything, no matter how degrading or humiliating, just as long as they get their 15 minutes of fame – and hopefully much longer!

But at least their story was really funny! And at least I think, so much better than watching Jerry Springer, and an angry confrontation between a furious wife and her transgendered husband’s lover, who is also a lesbian-identified male, and the guy who got her sister’s gay teenage daughter pregnant when he forgot to bring his dildo that night. Everybody ready for some major chair throwing?

And that’s entertainment? To each his/her own brand of madness I guess…

But yes, that couple’s story on Leno, in it’s own wacky and weird way, was heart warming as well as butt warming, drippingly sentimental, and maybe a good advertisement for WD-40 and also rubber mattress covers.

But most of all, it was majorly FUNNY!!! So I’m glad that she had whatever she has, to enable her to share it with us! As well as the rest of the world…


About Chris Sheridan

I’m a 56 year old guy who is young (and immature) at heart, and I love humor and laughter. Married for 22 years, but still enjoy all the glories of womanhood everywhere, even while dedicated to one woman only - and I hope my wife never finds out about her!
This entry was posted in Humor and tagged , , , , , , , , . Bookmark the permalink.

19 Responses to Most Embarrassing First Date

  1. That’s an interesting one to tell the grand children one of these days….

  2. xdeviantonex says:

    Well nice to see it was one of those love at first squirt kind of stories!

    As for the comment you made about people making asses of themselves these days for a short moment of notoriety I have only two words, reality shows!

    It is like driving by a car wreck, the average person does not care what happened, only if there is a good amount of carnage. Many examples to show the downfall of man range from jackass to jersey shore. Guess that is why some people are willing to swallow a bull testicle down with a seaotter shake. They are in the spotlight for a moment and getting paid for it as well, like you say.

    Goood thinking about the wd40, personally I go for 20w50 synth blend for less viscosity and thermal breakdown!

    • Reality shows… I could do an entire post on reality shows and the kind of people who participate in them, and I’m sure that you could too. We live in very strange times these days.

  3. Oh god that was hilarious!! And I love that they married LOLOL ..

    I am with you on what people call entertainment those shows that have everyone bitching at each other and airing their oh-so-dirty-laundry on air .. totally freak me out!

    I mean heck have they not heard of blogging!??! ;)

    • Glad that you enjoyed. :-)
      As far as those kind of shows, well I guess people have always loved freak shows long before TV or the internet. But I think that the carnival freaks had more dignity than some of these dysfunctional families who want to stick just how effed up they really are, in everyone’s faces, for all to see.
      Blogging? You have to be literate in order to blog… Most of those types don’t qualify.

  4. Hoo Sze Ling says:

    When I first started reading, I began to feel horrified. But knowing that they got married in the end made it kinda sweet and cute.

    Talking about “putting out” on the first date!

    • Lol @ “putting out” And I know what you mean about them ending up getting married. But if they are true soul mates, and this is how Fate brought them together, then Fate clearly has a sense of humor sometimes! Lol :-) Thanks for stopping by and commenting here. :-)

  5. Posky says:

    Everything about that story was fantastic. I’m going to give a friend nine cups of coffee and see if I can get into a similar situation.

  6. benzeknees says:

    Have heard this story about the couple on Jay Leno before, but it never fails to tickle my funny bone! I am so sick to death of all these idiots on TV trying to grab their 15 minutes of fame by doing more & more outrageous stunts. When is it going to end? Will someone have to die? Let’s hope it never goes that far! But in a day & age where celebrities are deified just for being celebrities, can we blame the general public for want some celebrity of their own?

    • Hiya there! :-) Yeah, I can also read this one over a few times and still chuckle about it.
      I’ve often thought about how back in 1968 Andy Warhol said that “In the future, everyone will be world-famous for 15 minutes.” and how it seems like he was predicting the social phenomena of youtube and Reality TV. I think the truth is that Warhol wasn’t predicting anything – he just thought that it sounded like a cool thing to say.
      But now it’s like everyone wants to be famous for at least 15 minutes, and for some, even if it means doing stupid and ridiculous things, or being famous for being repulsive and disgusting.

      But I can see what you mean about the worship of celebrity fame, and how it drives the mass appeal of a fame that anyone can attain, and often without the benefit of any real talent, but instead, just shock value or sheer novelty.

  7. Pingback: Feeling Left Behind and Out in the Cold? This One’s for You. | Word Play

  8. Teeny Bikini says:

    That. was. awesome! OMG! Have a great holiday! Loved it :)

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