The Most Experienced, Wisest Person Ever

Submitted by Chris:

Pauline was six years younger than I was.  We sent e-mails back and forth, called each other up, and decided to meet in person.  One weird thing about her: she seemed in a rush to impress me, so much so that she came off as a bit arrogant.  I'll give an example: I told her that I had a few relationships that ended bad.  Her response?

"Well, you don't know what a bad ending is to a relationship.  I've had so many that I'm a bit of an expert on them."

I'm sure she didn't mean to come off sounding "I'm better than you," but it wasn't just evidenced in this exchange.  Anyway, I figured that there would be nothing wrong with giving her a shot.

On the date, any amount of haughtiness that she inadvertently showed me before went through the roof.  The girl was dead set on proving to me how much wiser she was.  I felt like this went way past simple nervousness.

I told her, "I had a rough patch with my dad when I was in my mid-teens, but things are mostly better now."

Her response?  "You had dad problems?  The problems that I've had could fill a book!  I'm like the go-to girl among my friends whenever they have problems with their parents, since I've had almost every situation happen to me."

Okay then.  Uh... a good friend of mine passed away in high school.

"You think that's rough?  Three of my friends have committed suicide, two are still in a mental institution, and I'm the 'crisis person' of another one."

What a lively competition we were having.  I told her, "Wow.  You've sure had a lot happen to you."

She agreed wholeheartedly.  "I've had more things happen to me at 25 than most people in their entire lives!"

That statement was a monumental turn-off.  What a stupid thing for an upper-middle-class white girl from Kenilworth (Illinois) to presume.  Maybe I should've given her another chance, or maybe she was just super-nervous.  Either way, I wrote her off at that moment, and nothing more she said in our "bad-lives-pentathlon" made me feel anything more than a desire to stop spending time with her.

Someone with more experience.


  1. "What a stupid thing for an upper-middle-class white girl from Kenilworth (Illinois) to presume."

    Totally agree, I hate it when people claim to have such hard lives when they don't know they're born. Not that Im such an expert on it myself, but jesus I would have hit this girl.

  2. you could have backhanded her, then told her to add that one to her list.

  3. You think that's bad?? I've had MUCH worse dates than you!

  4. ^ I agree. You think THIS date was bad?! The girl from this date had someone hit her, rape her pets, steal her children and give her cancer! If only you could begin to IMAGINE what has gone on in her life!!

  5. This is another not a case of the bad dates.

  6. Should I feel bad at laughing out loud upon reading 12:41PM's comment?

  7. @ 2:50.........no

  8. Can you imagine what sex with her would be like? "You think that orgasm was good, wait till you hear about the one I had LAST night!"

  9. Once it was clear what her MO was, I think you should have tried one-upping her with the most ridiculous things you could think of. Start off small with something like "I used to hang-glide off of mount Rushmore until I was attacked by a pack of Bald Eagles" and then move on to how you invented time travel and are really disappointed that her name isn't Sarah Conner.

  10. This story has a happy ending. After this date, that girl packed up all her stuff, moved to nyc, started doing sketch and changed her name.

    You know her now as Kristin Wiig.

  11. Why on a first date were you bringing up parental problems, crappy past relationships and dead friends? I may have tried to out-drama you myself just to lighten the mood...

  12. she just one-ups you. big whoop. be glad it was just a one time date and not someone you have to see and talk to everyday...

  13. +1 5:53

    I can't imagine this guy gets many second dates when he shoots himself in foot with his mouth.

    I know women love to hear about failed relationships and all the negative things in their date's life because it sets a great mood.

    Keep it light and funny. No negatives.


Note: Only a member of this blog may post a comment.

Content Policy

A Bad Case of the Dates reserves the right to publish or not publish any submitted content at any time, and by submitting content to A Bad Case of the Dates, you retain original copyright, but are granting us the right to post, edit, and/or republish your content forever and in any media throughout the universe. If Zeta Reticulans come down from their home planet to harvest bad dating stories, you could become an intergalactic megastar. Go you!

A Bad Case of the Dates is not responsible for user comments. We also reserve the right to delete any comments at any time and for any reason. We're hoping to not have to, though.

Aching to reach us? abadcaseofthedates at gmail dot com.