How a Convict Killed My Relationship, But Probably Saved Me In the Long Run

Posted: September 12, 2016 in Humor, Relationships

Years ago I briefly dated a girl from Syracuse. She worked out at the V.A. Hospital and it was one of those deals where the more I got to know her the more I questioned why I was going out with her in the first place.

And to be fair, I’m pretty sure she was getting the same vibe from me.

Anyway, the more time we spent together the more uppity and pretentious she seemed to be. I got the feeling she sort of turned her nose down at us Southern Ohioans, ya know? She came from a wealthy New York family and wanted you to know it. Plus, every once in awhile she’d make a comment about one of my friends that made me wince a little.

She was always asking me questions that led me to believe she thought I might have some sort of shady past or something. I mean, I’d done some dumb things but had never been caught. No police record that is still on the books or anything. Bottom line I always felt like I was trying to prove I was good enough for her, and we’d only gone out a few times.

Not a good sign.

But, she was cute so I was willing to look past my reservations about her. She was also a former college gymnast at Syracuse, so she had that going for her.

Anyway, back then I was biking a lot and she was a fitness nut, so we planned a date that included rolling up Route 104 to Circleville, having a romantic (hopefully) little picnic, and heading back.

However, you know me. Best laid plans and all that.

Anyway, all was well as we cruised up the highway, riding side-by-side, talking about whatever. As we passed the Chillicothe Correctional Institute, we saw the prisoners were out in the yard. At this point she really started showing her conservative side, saying things like this:

Look at those thugs over there. What a waste of money. They should all be fried.”

Or . . .

“I have no sympathy of those animals. Look at them having a good time. It’s disgusting.”

Wait. “Having a good time?” I mean, they were in prison after all. Didn’t look fun to me. Still, I’m pretty sure I kept my comments to the occasional, “Yep.”

And then it happens. From the corner of my ear I hear this:


So I look over and there, running along the fence, was an inmate yelling at me. It was a guy I’d gone to high school with and hadn’t seen in forever, mainly because he was doing a 7-10 year stretch in The Slammer.

Oh, for the love of God.

Why me? What were the odds?

At that point I gave him a sheepish wave and kept going. Actually that was my only option since I didn’t want to get shot running over to the fence. It was only when I looked over at my date did I notice I was getting The Judgemental Stare of Death.

I was sort of speechless but I finally said this:

“What? I knew the guy in high school.” 

But she wasn’t buying it. It confirmed her worst suspicions. The rest of the ride was awkward, mainly because she was now convinced I had a horde of convicts as friends.

You won’t be surprised to learn that it was our last date.

Now that I look back at it, my old friend the convict probably saved me from a lot of future stress and annoyances.

Thank God for convicted felons, I guess?

  1. Joe says:

    Damnit I thought the story was gonna end like this “I have a beautiful wife now and the chic i was with then is in prison now” lmao

Gimme a holler.

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