Twice per month, without fail, the two most different people in my life cross paths.  One is a young, energetic white woman excited about her life.  The other is an old, exhausted black man who regularly prays for death.

They have nothing in common.

Except me.

She was a late bloomer, a college dropout movie theatre manager who found her way and graduated with honors from UCLA, earned a Masters degree from Bristol University in the UK, and is now in the PhD. Program at Virginia Tech.  Her name is Caitlin.  She is my eldest daughter.

He found success young, a college football player who lost his way and descended into drugs and spiraled from user to addict to dealer to killer.  His name is Charles.  He is my prison pen-pal.

She grew up privileged.  He grew up fast.

She has spent 30 years on planet Earth.  He has spent 30 years in a federal penitentiary.

She will someday be known as “Doctor.”  He will forever be known as “Bed 122889.”

The fact that I have a daughter does not surprise most people.  The fact that I have a prison pen-pal surprises everyone.

It started, as many stories do nowadays, on Facebook.  Between the semi-forgotten high school classmates I didn't even like back then and the bazillion Roller Derby girls and the total strangers who Friended me for no apparent reason, I came across the profile of Thomas “Hollywood” Henderson, a badass linebacker for my favorite football team, the Dallas Cowboys, back in the '70s. He played in three Super Bowls.  Hollywood's life has been something straight out of, well, yeah, Hollywood.  His story has a familiar and predictable start:  football star to drug addict to prison.  But then it turned:  unlike many, he turned his life around and became a drug counselor.  Then it turned some more:   he won the lottery.  Did he fall off the wagon and plunge into the abyss?  Not hardly.  He stayed clean, and was rewarded by the universe by winning the lottery again.  I Friended TH (as he refers to himself) and followed his posts.  I liked them.  And him.  He is honest and open and often refers to his addiction and his recovery and even manages to drop God's name in there once in awhile without being preachy (no small feat).  I'd comment on some of his posts and sometimes he'd reply (or laugh) at one of my comments here and there.

One day TH posted asking his Facebook friends to contact someone he knew from the old days.  Charles.  He said Charles was forgotten and alone and no one deserved to be either, much less both.

I did a little research.  Charles had killed a man in a drug-related argument.  Convicted of Manslaughter.  Theoretically eligible for parole.  Theoretically.

And then, as one of those do-gooder guys, I wrote my first letter to a prisoner.

A week later, Charles wrote me back.  Handwritten, old-man shaky (he is about 60 but, having spent half his life in prison, he writes and sounds older).  He seemed thrilled to have some outside world contact.  He explained a little about his plight (unlike most inmates he has never claimed innocence; his plight referred to his inability to secure parole) and asked if I would help him.  He attached a long list of names of people he wanted me to contact on Facebook (full circle!) to ask them to write to him.  He had a parole hearing upcoming and was looking for character support to take to the parole board.  I said sure.  But many of the names were common, and some of them were not on Facebook.  I wrote back and said I needed better descriptions – approximate age and ethnicity would help.

Thus began several months of back and forth, receiving his lists, detectiving on Facebook, and writing to his people.  I had no idea who they were to him, where he knew them from, what they thought of him.  In all I believe I wrote to about 100 people.  To the best of my knowledge, none ever responded to Charles.

Charles writes me back like clockwork.  Caitlin on the other hand has never sent me back a card.  If she wants to say hi, I get a text or e-mail.  But having visited her, at various places across the country and the world, I have seen all my cards proudly displayed.  At two per month, they mark her time away the same way a prisoner might use chalk lines to mark his time inside.

In the meantime, every couple months I go on a card-shopping run.  My local Hallmark shop at the mall closed, so I'm pretty much limited to my local Rite Aid drugstore and the supermarket.  I rarely vary in my searches.  The “Miss You” section for Caitlin and the “Encouragement” section for Charles.  Neither is as varied as you might think.  The cards all look very familiar, and I wouldn't be surprised if over the years they have received duplicate cards from me.  But both wisely never mentioned it if they had.

Writing content to Caitlin is easy.  I tell her how I'm doing, how work is going, the latest I have heard from her sisters, sports update (the Dodgers if it's baseball season; Cowboys if it's football season), weather update, tell her that I miss her and I love her.  Done.

Writing to Charles has proven more challenging.  Encouragement is good, sure, but encouragement to do what, exactly?  For a long time it was a matter of keeping his spirits up while awaiting his parole hearing.  Eventually though, that day came – and did not go well.  Denied again.  Charles was despondent.  Talked suicide.  And I had to really think about how I wanted to respond to that.  It's easy to say don't do it, you have so many reasons to live.  Problem was, I couldn't think of many.  But ultimately I decided to tell him to hang in there, that of course the news was a devastating blow but my God, after 30 years surely he had built up a high tolerance for pain.  Plus I added there is always a grace in doing for others, and that giving brings its own joys – just as I had received joy from writing to and hearing from him.  He wrote me back – he heard me.  And somehow he gets up in the morning and makes it through another day, even though he and I know full well he will never live another one as a free man.  Neither of us say it.  But we both know it.

And on it goes.  My “I miss you” cards to Caitlin and my “There but for the grace of God goes Caitlin, or her sisters, or me” cards to Charles. I feel so badly for him.  And so happy I am not him.

My daughter Caitlin will soon be coming home for a family wedding.  My prison pen-pal Charles will never go anywhere again.  They will never meet, one with more things to do than time to do it and one with nothing but time.  One with everything to live for and one with nothing to live for.  They live in the same country at the same time but in different worlds, in different skins.  The only thing they have in common is that on the 1st and 15th of every month, envelopes with their names on them are placed into my mailbox, and in those few hours until the mailman picks them up, their lives, unbeknownst to them, touch.  

R.J. Colleary is a writer living in California.

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THE 1ST & 15TH

R.J. Colleary