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Lifestyle

I had a hot summer fling in the Hamptons, but ended up visiting him in prison

News RoomBy News RoomMay 5, 2026No Comments6 Mins Read
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I had a hot summer fling in the Hamptons, but ended up visiting him in prison
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  • NY Post staffer Jeanette Settembre’s new novel, “Little Red Flags,” is based on a dark romance.
  • Settembre’s summer fling in the Hamptons turned dark when her lover killed two in a drunk driving crash.
  • She secretly visited him in prison, struggled with his control, then broke free to heal.

The summer I turned 25, I had a hot fling with a handsome, brown-eyed stranger one weekend away in the Hamptons. 

He was sarcastic and direct, with a sensitive side. We had instant chemistry. I’d never been in love before.

Afterward, I returned to New York, and he went back to Boston. We texted and drank wine together over Facetime. He showed me his two cats. How his husky could howl “I love you.”

He told me he’d “save up and plan a trip to New York soon,” to visit me, if I wanted. I did.

Then I didn’t hear from him for several days. Instead, his friend sent me a headline about a drunk driver who killed two people in a crash. It was him. 

I was in shock. How could he have been so reckless?

Growing up, I had perfect attendance in school and always made the honor roll. I had never even gotten a parking ticket.

My life, at that point, was near-perfect. I had a dream job as a food columnist at a major newspaper, eating at Michelin-star restaurants and interviewing celebrities. I didn’t want to derail everything I had worked so hard to build. I knew I needed to cut off all contact with him. 

Instead, I texted: “Heard about what happened. Hope you’re okay. Thinking of you.” 

The next time we spoke on Facetime, his face was scarred. Glass from the windshield still pierced his forehead.

“I can’t believe you’re still talking to me,” he told me. He tried to convince me not to, but I could feel how desperately he needed me..

We kept talking and texting. He attended AA meetings and prayed daily with a rabbi asking for forgiveness.

Ashamed of his crime and uncertain about the future, I kept our relationship a secret. I thought he was my best friend.

Jeanette Settembre

He was arraigned and made bail in the fall. When he called me to tell me he was visiting his brother in New York that December, I didn’t know how to feel. I was nervous – I didn’t want to meet his family and get more attached. But, I also thought it would be nice to see him. Soon, I was applying red lipstick in the back of a cab headed to his brother’s apartment building.

When we kissed in the elevator of his brother’s downtown apartment, my mind went back to the night we met. He remembered my perfume.

He returned a few weeks later and we spent New Year’s Eve together. Tears streamed down his face as we watched the fireworks from a boat on the Hudson, feeling guilty that he was able to take in a moment he took from the victims and their loved ones. 

Our relationship unfolded while he awaited trial. 

He’d travel down from Boston on the Bolt Bus to see me with sunflowers every few weeks.

When I visited him in Boston for the first time, he cooked me breakfast, and researched the best Italian restaurant in the city, where he told me he loved me. 

That spring, we visited his beloved grandmother in North Carolina, marveling at the Blue Ridge Mountains together.

Ashamed of his crime and uncertain about the future, I kept our relationship a secret. I thought he was my best friend.

We were together about a year before he was granted a plea bargain. He pled guilty and got seven years.

I told myself I would cut off contact with him when he went to prison. Instead, I found myself in a sea of stroller moms at an Upper East Side Ann Taylor Loft, searching for an outfit to wear to visit him.

Initially, visiting him in prison felt daunting, but I got the hang of it. It was like a DMV. You pick a number, fill out a form with the inmate’s number, wait to be called in a group and go through a metal detector.

The first time I went to see him, we talked for five hours straight holding hands. 

It was a medium security facility so they allowed lengthier visits. 

He pointed out the inmates who were “lifers” and the white-collar criminals in for money laundering. 

I saw wives visiting husbands, kids visiting fathers.

The only thing I could bring into our visit was a plastic card loaded with $40 for the vending machine.

Medium security prisons run on vending machines stocked with bottled Dunkin’ drinks and a calzone type snack called a Rip-n-Dip. Little luxuries. 

Catching up over comfort food, it felt like it was only us, despite being in this dark, harrowing place.

In lieu of cologne, Ben used a fragrance sample from a magazine to smell good for me the handful of times I visited.

As his sentence wore on, Ben became increasingly controlling and manipulative. He would make me feel guilty if I sounded distracted on a call or didn’t attend his family’s events, like a Zoom Passover, in his place.

Two years into his sentence, I told him I needed to move on. He cruelly told me no one would ever love me as much as he did. 

He needed constant reassurance that I wouldn’t leave him, which I couldn’t, of course, give. He told me that this experience would make our bond stronger, that I was lucky to have found someone who loved me so much

I grew increasingly depressed. I was consumed with guilt and lost my appetite for food and life. I started having panic attacks that necessitated trips to the ER.

Friends began moving through milestones in life — marriage, kids — while I was stuck in neutral.

I stopped answering his calls, started seeing a therapist and wrote the words “Just Keep Moving Forward” on a piece of paper and taped it above my desk.  One day at a time, I took back my life.

He was released from prison after five years. He never contacted me.

I’m now 34 and married to a wonderful man. For years, I was too ashamed to tell this story.

Now, I’ve written a novel about it — a dark romance called “Little Red Flags” — out tomorrow. Sharing it with the world has been healing.

After all these years, I’m finally free.

Read the full article here

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