On Love and Prison: How The Criminal Justice System Has Failed Us

01/05/2017 11:35 pm ET Updated Jan 06, 2017

When I was in high school, I fell in love for the first time. It was a fearless kind of love that was genuine and fun. He was older and pretty much everything I never saw coming. He’d show up out of the blue with a bashful smirk and hover by my locker until it was safe to skip class. His timing was impeccable too; I hated math and had already determined its lack of significance in my life. Plus our connection was undeniable. He had a soft, unassuming side that drove me crazy. I loved the way he honored us, making me his magnet. And though we were young and carefree, still learning how to successfully function in society, there was always a deep understanding between us — even though we came from two wildly different worlds — from opposite sides of the tracks. But as days turned into months, and months turned into years, we watched each other grow wholeheartedly, for the better . . . and from the walls of a jail, desperate to make sense of the hand he was dealt.

Raised in an upper middle class household with sit down family dinners, a canopy bed with ruffles, and regular sack lunches with the words “have a good day, I love you” written on a napkin from my mom, only proved how fortunate I was. Rules and curfews and vegetables were non-negotiable, sometimes making me feel stifled and misunderstood, especially as the stubborn recluse of the family. Nighttime would come and I’d still be stuck at the kitchen table per my father’s commands, refusing to eat my broccoli. I fucking hated broccoli, and was determined to make a point for as long as I needed to, knowing that every second I sat scraping my fork against the plate — pushing the veins in my dad’s neck to bulge — that I was loved more than anything in the world.

When I met my then boyfriend (we’ll call him “J”), I knew my parents would disapprove. “He’s on the fast track, Natalee,” they’d say, reminding me about my extracurricular activities and school — and sessions with my awkward math tutor who never figured out how to pluck the hairs from his nose. But I didn’t care. The loss was too big to bear. Besides being in love, J needed me. His reality was tightly wrapped in survival mode, leaving him to fend for himself after his drug addicted dad abandoned the family. I saw the hopelessness envelop him everyday. I saw the fear sneak up inside of him as he waited for his mom to come home from one of her three jobs. So when he would show up at my locker, full of adventure — and valid reason to escape, I nearly followed him to the ends of the earth.

After a year of begging, my parents finally caved and got me my own phone line for my sixteenth birthday. I continued to keep J’s struggles private, knowing it would only lead to more questions, until one day, while I was at school — standing alone at my locker — my mom overheard him leave a message from the county jail on my answering machine. It went something like “wrong place at the wrong time. I’m sorry. Know that I love you. Go to math.” The truth was, he wasn’t at the “wrong place at the wrong time.” He made a poor decision — albeit with good intentions — and got caught, recklessly trying to survive his circumstances while everything around him fell apart.

I paced my bedroom for days, quietly trying to figure out how I could get into the jail to see him, which was impossible without a parent or guardian. I barely left my room because I was afraid I’d miss his collect calls. Time ticked slowly, making me lose hope, until one day my mom knocked on my door, told me to get my things, and that she’d inform my father about our visit after we came back. I knew she didn’t want to take me — and that it was well beyond her comfort zone, but she did it anyway. And goddamn did I love her for it. Never have I cherished another human being the way I cherished my mother that night. She saw me . . . and felt every blow of my sadness.

As expected, we looked like a couple of deer caught in headlights as we entered the prison. We were a sitcom waiting to happen.

“How does my lipstick look?” my mom asked, her button-up freshly ironed and hair sprayed into thick curls. I laughed, wiping sweat down my jeans while an officer handed over our paperwork.

“And my teeth, anything in my teeth?” she continued to ask, smiling awkwardly.

“Seriously?” I laughed again, imagining what my father would think once he caught wind of our whereabouts.

I watched as she signed our names, wondering what would happen once the anticipation wore off. Luckily, the wait wasn’t too long and we were escorted into a small booth with a large piece of glass separating our good intentions — and quiet fears.

“You okay, mom?” I asked, hoping her claustrophobia was under control.

“Couldn’t be better,” I remember her muttering under her breath as she held onto the wall, her sarcasm far from lost.

Together, we silently watched as groups of men wandered around a windowless room, wearing bright orange jumpsuits and black sandals. My body felt like Jell-O as I watched J make his way up to the booth, his smile cautious and his eyes weary.

“Thank you,” he said, looking at my mom as he picked up the phone and sat down. I waited while he stared at me through the glass, quietly examining my trembling hands before moving his gaze back over to my mom . . . who stood in the corner with full-blown hives and a steady casing of tears.

“Natalee,” he spoke softly, waiting for me to make eye contact. “It’s going to be okay.” Gripping the phone cord, I sat unable to speak. All I could do was stare at him and wonder how his life would’ve been different had he experienced the same kind of stability and care that I did. I longed to see him happy and resolved, but instead I saw his coked out dad and resentful mom rob every ounce of his being, leaving him to pick up the pieces and somehow persevere unscathed. I wanted so badly to ask him: what would’ve had the power to change your course?


For the past few weeks, I’ve been reading a number of open letters to President Obama regarding criminal justice reform, which has brought these memories back in strong waves. So much that it feels like it was just yesterday. John Legend, a tough advocate — and someone who has courageously spoken about his own mother’s substance abuse and incarceration — has shed new light on the inequalities and “moral failings” that continue to plague our justice system, particularly for non-violent drug offenders and juveniles. With the U.S. having the largest prison population in the world, it’s alarmingly evident that a serious problem exists within our policies. There are 2.2 million people in the nation’s prisons — with half of the people serving time for a non-violent drug offense.

Adam Foss, another powerful advocate for criminal justice reform, and a Boston prosecutor with the best set of dreadlocks I’ve ever seen, posed a critical question at the start of his 2016 TED Talk, asking the audience for a show of hands: “who in their late teens or early 20’s shoplifted, tried an illegal drug, got in a fight, or drank alcohol before they were of age?” Many hands went up around the theatre, prompting Foss to ask another important question: “how many of you think you’re a danger to society and should be defined by those actions?” Not a lot of hands went up, expectedly so.

Let’s be clear, I’m certainly not giving away free passes, or condoning certain behaviors, but I do believe, with great conviction, that there are disenfranchised individuals hopelessly stuck inside a vicious cycle of victimization and reduced circumstances rife with trauma and abuse. I’ve seen it firsthand, as well as the pain and suffering that can follow — while juxtaposed with the troubling lack of rehabilitation, mentoring, and mental health services within our justice system.

Foss’s story about his role in a young man’s sentencing — and life, resonated profoundly. Christopher was a senior in high school and dreamed of going to college, but made a stupid mistake and “ripped off 30 laptops from Best Buy” to resell online. Instead of charging him with “30 crimes,” Foss took the time to get to know Christopher, who subsequently made restitution, served community service, and had the opportunity to thank Foss by saying, “You cared about me. You changed my life.” Today, Christopher works in banking — and is a great example of what can happen when we prioritize criminal justice reform.

Furthermore, Christopher’s story strongly supports The If Project’s praiseworthy mission— and award winning documentary, which focuses on “intervention, prevention and reduction in incarceration and recidivism.” The collaboration includes law enforcement, as well as current and previously incarcerated adults. The project is also based on one significant question, which resonates deeply with me: “If there was something someone could have said or done that would have changed the path that led you here, what would it have been?” Most inmates shared similar sentiments, bravely expressing how much weight — and inner transformation — one question can provide.

I know J was deserving of my love and compassion. I saw his light, even when he diminished from it. And whether we admit it or not, we’ve all wanted a second chance, somewhere, somehow . . . along this hard and unsteady terrain called life.


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