Lovelorn Lookyloos Into the Prison Pen Pal Program

Imprisoned Bachelorette #3: Ruby

AGE: 26
HEIGHT: 5-5
WEIGHT: 137
HAIR COLOR: Blonde
EYE COLOR: Blue
SEXUALITY: It’s Complicated
MARITAL STATUS: It’s Complicated
CHILDREN: It’s Complicated
CONVICTED OF: Bank Fraud
CURRENT RELEASE DATE: 11/01/2011

“Ballers holla @ me!! Seeking male who will treat me like the princess I am. Loves hard working honest men. Hates dishonesty. I love to be naked. I do everything completely naked. Dishes, housework, EVERYTHING! I think I miss being naked the most. Do you like to be naked?”

My thoughts: Woah, woah, woah! Let me get this straight: “Hates dishonesty?” You’re guilty of BANK FRAUD! And speaking of dishonesty, how about you post an actual photo of yourself, and not one of Scarlett Johnasson.

But what do I expect from a website with ads for “Online Scuba Lessons”?

A couple of months ago this same site changed its slogan from “Single women that need you to write to them” to “MILFs in prison – Women that want you”.

After much deliberation (i.e. ogling), I finally picked a winner:

IMPRISONED BACHELORETTE #1!

I’ll learn her name later.

Yeah, I know Bachelorette #2 was the clear favorite. But there’s no way I stand a chance with a classy convict like her. And I have the nagging suspicion that Bachelorette #3 is really a man. Wouldn’t be the first time…

The next step was to send the lucky “winner” a message introducing myself. I also included a couple photos of yours truly. I wanted something that said “sensitive and hip” without making myself look like a giant douche bag:


Definitely not a douchebag.

And here’s my dashingly romantic letter:

And so my romantic dreams were dashed against the proverbial brick wall like so many hot female convicts in a catfight. I wonder if the Humane Society has euthanized those two grey tabbies yet? Maybe I still have a chance…

Today’s Real Winner (Tie):

Chairman Meow and Fidel Catstro

Pages: 1 2