They say there’s never a good time to break up with someone.

It’s always either an upcoming holiday (you can’t break up with someone on Christmas!!!) or it’s someone’s birthday, or graduation or JAZZ FEST and then there’s that already-booked vacation to the mountains coming up and no one wants to lose their deposit on a villa.

But even if you somehow find a lull in your (and your significant other’s) schedule you then need to figure out the best place to break up with them.

The most humane place possible. Like euthanasia.

Would it be more pleasant for someone to be broken up with in private? Or a public place?

Would breaking up in the apartment you share together make it awkward because then, who leaves?

Or would it be worse having to tip a server once the conversation was over?

I certainly don’t know what’s better, but I can tell you from personal experience the absolutely, unequivocally WORST time and place to dump someone:

The day before their birthday.
On a boat.
In front of parents.

This happened to me three years ago to date.
Well, three years ago to date yesterday.

See, TODAY IS MY BIRTHDAY (Go shorty!!) and thanks to Kyle, I will always think back on the year my super courteous boyfriend broke up with me the day before my birthday. On a boat.

And we didn’t get to dry land after that for another 45 minutes.

Kyle and I had dated on and off for two years and I broke up with him the previous November and we were doing the super successful “let’s still sort of date to see if we can work it out/lessen the blow” thing.

But that just made the break up more torturous, and one particular fight (that he started) ended in a dramatic “CAN’T DO THIS ANYMORE! IT’S OVER!!” finale.


Kyle’s parents busied themselves with what little they could find on the tiny motorboat, after overhearing the entire conversation.

I was considering taking a life jacket and jumping overboard. I remember staring at the water, wishing I was a dolphin.

“I guess you don’t want your birthday present now huh,” Kyle said, interrupting my dolphin thoughts and I almost slapped him.
I had actually forgotten it was my birthday in my state of shock.

“What it is?” I asked, quietly.

“A motorcycle helmet,” Kyle said.

The pink, half-shell helmet I was supposed to wear when riding on the back of his motorcycle.

I glared at him through my red teary eyes and shook my head in the way people do when they’re trying really hard to suppress full-on rage.

OH, Kyle GUESSED that I didn’t want the present that can only be used by spending more time with him?

His dad coughed from the back of the boat.

I sat by myself in the front of the boat all the way back to the marina and then spent another 40 MINUTES in the car with Kyle and his parents back to my house.

I insisted that my twin sister, Joy, would pick me up from the marina, but Kyle’s dad refused to leave me there by myself.

I didn’t say anything in the car ride and did my best to not sniffle too loudly.
Thank God for big round sunglasses that cover half your face.

When we got to my house, Kyle’s mom got out of the car, gave me a hug and said, “I hope you have a Happy Birthday,” and then paused and added, “Well, a Happy Birthday considering…”


I returned the hug and said thanks, and we both knew we’d never see each other again.
And we both knew that her son was an asshole.

So, while there’s no good time or place to break up with someone, breaking up with someone on a boat the day before their birthday in front of your parents is probably the worst place to do such a thing, aside from the delivery room and the alter.

Ruining someone’s birthday in this manner will also get you in trouble with the karma Gods of the Sea.

Because, haha, not even a year after the breakup boat scene, Kyle accidentally SUNK HIS BOAT when he had too many people on board and a big wave overtook it.

It sank to the bottom of the harbor like all of our hopes and dreams, and “Sea Tow” had to fish it out for a hefty price.

I laughed my ass off when I heard about it, and laughed my ass off again when I repeated the story to everyone I knew.

Including my parents.


One thought on “TOOLBAG TUESDAY

  1. Anonymous

    Well, with a name like Kyle, he MUST be a douche. 😉 Just kidding!

    It makes a great story! And a douche like that does not deserve Jennay. My favorite line… “And we both knew her son was an asshole.” Totally!

    There are so many tools and douches out there, I think you should practice your Spanish and expand this concept to “Douchebag Domingo” and write a Sunday blog.

    Love ya,


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