Dating After Prison – NHSEB 2020-2021 National Case 10

My friend Jamey spent a total of 6 years in prison. Today he’s free and thriving. And just a few months ago, he got married. I asked him to review NHSEB case 10, Dating After Prison. What were his thoughts?

Boxing teammate and friend Jamey with wife Peyton

A natural athlete, Jamey had been a star running back in elementary school. He was fast. Scary fast. “Who’s that little white blur?” fast.

Then in the 7th grade he developed chronic knee pain. No longer the fastest, his popularity and self-esteem took a hit, and he turned to substance abuse.

A couple of years into high school his knees were better, but the bad habits remained. He switched to a vocational track to graduate, and played well enough to earn a football scholarship. It was in college that Jamey got his first opportunity to sell drugs. He found that he was naturally good at that, too.

A drug dealer’s life doesn’t mesh well with the demands of higher education. And when the college experiment failed, the downward spiral accelerated. Jail time became prison time, and winning $50k from a scratch-off lottery ticket just made things worse.

The above excerpt is from Year of the Fighter: Lessons From My Midlife Crisis Adventure, my 2018 memoir on how an ethicist overcomes childhood bully shame by doing something he’d always dreamed of doing – competitively boxing and kickboxing.

Jamey was a teammate, mentor and coach at my boxing gym, Monroe County Boxing Club. He taught me how to not to not be “a moving punching bag,” how to use my endurance as a weapon, and how to push my body into beastmode and beyond.

When we met, he’d already done significant time behind bars. And while boxing kept him straight for a while, he relapsed and found himself in trouble with the law once again. The judge gave him the option to either go back to prison or to Miracle Lake, a rustic Christin rehab facility near Etowah, Tennessee. Jamey took the chance, and the experience changed his life.

He’s been clean and straight ever since, and this summer my family attended a beautiful outdoor wedding where he wed his soulmate, Petyon. I remember when Jamey and Peyton first began dating, and I was there when he proposed during intermission at the annual Monroe County Boxing Club Rumble. So when I read case 10, he immediately came to mind.

He agreed to discuss it, and explained that when he graduated from Miracle Lake and thought about dating again, he wanted to be as transparent as possible about his past.

So he shared his background on his Facebook page, regularly posting about the dark places he’d been, and how much better life was on the other side. He would also share his testimony at church, which is where he and Peyton met. As Jamey put it, “I didn’t want anyone to feel deceived. I wanted to be accepted for who I was.”

However, while he wanted church friends and love interests to know as soon as possible, he didn’t think disclosing his prison time was as important for casual friendships (see ethics bowl case discussion question #3).

“About the friendship thing, that’s not as important to reveal right up front… You wouldn’t want her to find out and feel misled. But with dudes, it may not even come up for a long time. But Peyton, she knew everything. I feel that was important.”

In contrasting the gentlemen in the ethics bowl case (Antoine and Jack – see discussion question #2), Jamey thought they were clearly different. “There’s definitely a moral difference due to the type of crime and their time in prison. One was innocent, the other admitted it.”

Jamey argued that the differing amount of time served by Antoine and Jack – Antoine, 8 years, and Jack, 27– was especially relevant.

“The longer you’re in there, away from society, the more of a criminal mind you could have. Not everyone, but someone doing that much time is definitely going to be different. Their frame of mind – someone doing that much time – it becomes truly institutionalized.”

The implication seems to be that a person would have a stronger obligation to reveal their prison time sooner when a) they were guilty, b) their crime was violent and c) lengthy prison time had altered their character in negative ways. These are all things a potential life partner would want to know. And so Jamey argues they’re better to share immediately in the interests of building trust.

However, Sequoyah High School Ethics Bowl team member Juli Brackett argues sharing prison time could and should wait until the third date. Why date #3?

First dates are often shallow chit-chat. Second dates, when they happen, suggest agreement that there’s long-term potential. But by the third date, it’s clear both parties are open to a serious commitment. The emotional attachment approaches an unspoken but significant threshold. And that’s when someone who’s been to prison should disclose it, argues Juli.

Why not share it on or before date #1? Juli argues this could sabotage what could become a beautiful happily-ever-after. If everyone shared their darkest secrets up-front, no one would get married. Waiting puts both parties in a better position to put past mistakes into context.

The up-front approach worked for Jamey. But maybe he was especially charming. Or maybe the fact that he and Peyton met at church reassured her he was a changed man.

Whether Juli’s or Jamey’s approach is morally best is arguable. But three factors that seem unarguably relevant: 1) whether the person was guilty, 2) the nature of their crime, and 3) time served and its impact on their character.

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