Love Letters from Prison

When soulmates become cellmates

Technology is a crazy thing sometimes… Wait, this post has absolutely nothing to do with technology! Let me re-boot here; Many people believe that things happen for a reason. I don't really subscribe to that notion, but it's little things like what happened the other night that make me question my stance. I was hanging with my sweetie and one of her best friends. Eventually we started talking about dating and mating (what a surprise) and that's when things became a lot more interesting when talk of a prison pen-pal cropped up!

I was drawn in and began rubbing my hands together in anticipation. Apparently my gal's friend, Sarah, was getting some sexy correspondence from a local inmate. I was floored and it was awesome. I've never known anyone who had been exchanging romantic messages from a prison inmate. AWESOME!

Instead of getting too deep in details, I figured I'd share the letter here. I've changed the names so as to protect the apparently non-innocent, otherwise everything else is verbatim, even misspellings.

Wednesda July 14, 2010

Dear Sara,
How are you? I'm good. Just a chillin' villain. This is Angel's good friend, Keenan. Hopefully you saw my photo & are up to your standards physically.

This probably about the only time I've appreciated the phrase “chillin' like a villain.”

As for the rest of Keenan, I am tall. 6ft and 195lBS. Got a cool build. You know how “they” say the typical convict reads every book and works out all the time? Here about, 1/2 of people locked up work out regularly or are educated. I am one who fits that category I guess. So my mission is to get that bedroom body hard as steel I'm almost there too. Not conceited or feel like I am better than N-E 1 but I am confident.

Crafting abs of steel behind bars of steel. Nice! Oh and referring to himself in the third person is a nice touch, too.

Keenan is very playful, sarcastic, love to laugh  & have fun & make jokes out of situations to ease tension.

Keenan is approaching Shatner levels of self interest.

Yes, you'll laugh hella hard & my smile is infectious. You notice how you have sick or negative people that you wanna strangle? Not me. I got a good heart & like to lookout for people. Stay positive, rain or pain.

What am I going to say here, people? Maybe, just maybe, Keenan has given us just a little insight into how he got into prison in the first place. (Urban Dater Pro Tip: If writing to a woman, from behind prison bars, it would be wise to avoid using violent terms. Example: “strangle.” Bad, bad, bad)

No one is perfect and never do I claim to be. I have a habit of being brutally honest & won't lie. It's bad because you come across people who are controlling & only want your truth to be theirs, or demand the real but can't handle it. I also blaze herbs every now & drink from time to time. I am not one that goes clubbin a lot. I do play pool & will whip the skinn of anyone. You are included Yes ma'am dominoes, chess, pinochle, checkers, darts, video games, I'm “init”.

Pinochle? Really!!?

I dress for the occasion but prefer to dress casual. you know, some slacks & a button down wit some duffalinos or Stacy Adams is cool. Summertime is mandatory shorts & tank tops. Like now, it feels like we're stuck in the Amazon or on the Sarengetti. It's cool though cause in this weather you sweat more during the workout. You got a music lover, animal lover, & kids are the shit 2. They're funny. But I listen to damn hear everything. Reggae, reggaetion, Salsa, Cumbia, Megengue, so you know.

I have to give up to the guy for recognizes the value of Stacy Adams footwear. I'm just sayin'.

Hope to hear from you soon. For real. Thanks for shooting your hook-up. Get at me.

Yours Truly,
Keenan Sampson
CDC #V007885
PO Box ——
San Bernardino, CA 92860


Is it cool for me to call you sometimes on your cell phone? Yeah you dealin with a gentleman & a respectful individual.

If this isn't the start of something loving, I'm not sure what is.

Author Profile

Alex is the founder and managing editor at the Urban Dater. Alex also runs: DigiSavvy, for which he is the co-founder and Principal. Alex has a lot on his mind. Will he ever get it right? If he does, he'll be sure to write.

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  1. Hi Please check out my website I am in the middle of writing an article about women and men that fall in love and marry prison inmates. A large number of sociopaths are found in prison they have plenty of time to hone their skills. I would love to use your letter a perfect example (of Course with all credits due): several things in this letter give him away and I would love to pint them out. thanks

  2. My husband is in the Federal house terminal island Cali. He’s been down 6 years married him in Idaho 2010 he’s less than 90 days to half way house. Many love letters. I love Brian I’m his wife Rayne

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