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Column: Jillian Hamilton takes an honest look at romantic relationships

By Sarah Bamford

Last month I ran into the fearless podcast host Jillian Hamilton at Bistro V on Greenwich Avenue and we had a chance to catch up. I originally met Jillian a few years ago at a birthday dinner for my friend and Greenwich real estate agent, Suzy Armstrong. I remember Jillian had on a chic fur jacket that she had custom-made in New York City as part of her line of bespoke furs. Fast forward to last spring we bumped into each other at Katie Fong’s boutique on Lewis Street where Jillian was hosting a trunk show for her fur collection. That day Jillian told me about her latest project, a podcast titled ‘Cheating: When Love Lies’. I asked her to send me the link. For the next week or so I was listening to her jaw-dropping interviews mixed with fictional short stories about cheating and affairs while on walks in Havemeyer Park with my rescue dog, Sumi.

At first, I wasn’t sure this podcast was my cup of tea. I wondered if I would become jaded from listening to dramatic stories of heartbreak and betrayal but what I realized is that the information being shared was powerful because it was real. Once the listener gets past the excruciating and awkward details of infidelity, there is a pure vulnerability that feels redeeming. By asking the right probing questions, Jillian helps her audience feel empathy and even identify with her guests, both the adulterer and betrayed partner. The podcast takes a deep dive into varied points of view when it comes to romantic relationships of every kind.

It’s strange, as I listened to the episodes I felt like Jillian was asking all the questions that popped into my head. With the utmost compassion, she flawlessly guides her guests, anonymous mostly, in exposing their most intimate stories. They confess to cheating on the people closest to them or walk us through being cheated on, her guests explain the passion and pain that comes along with it and we’re left with the question – are the secrets worth it? It becomes a therapeutic experience. Jillian is able to disarm her guests and give them the ability to be open about their explicit experiences in love, lust, and everything in between. She has a gift for connecting with her guests and gaining their trust.

Jillian first launched a YouTube channel in March 2021 to share her fictional stories and interviews about infidelity and was quickly offered an exclusive deal with one of the leading podcast networks called PodcastOne. She now has a two-year contract with the network and has one of the featured podcasts alongside major journalists and celebrities. It was the subject matter that got the network’s attention, the conversation she was having with friends that she felt needed to be shared on a larger scale.

Jillian moved to Greenwich in 2019 but her daughter has attended private school in Greenwich since 2010. An active member in the local community, Jillian is on the Bruce Museum development and DEI committees. She was also one of several to help select the new curator at the New Bruce. When I asked Jillian what motivated her to be proactive in addressing the issue in such a public way she explained, “life”. She’s been on both sides of infidelity throughout her adult life and experienced it in her home as a child. “As I began to talk about it I saw that so many other people also had experienced it in some way or another,” she said. Jillian continued, “I realized no one was talking about cheating in a way that wasn’t salacious and gossipy but instead in a way that could be helpful and empowering”.

Jillian’s mission with each interview is to uncover the “WHY” for each guest on her show. She helps her audience understand how unconventional and complicated relationships happen and often discovers the answers are deeply rooted and painful. Through hosting the podcast Jillian says she’s learned that many people have a private internal narrative about their love life with thoughts and feelings they are unwilling or afraid to share with their partners.

What’s interesting is that although most of her guests discuss full-blown affairs, others talk about secret emotional relationships in addition to long-term faithfulness. Jillian pointed out two shows that purely focus on avoiding temptation and fidelity that I suggest you start if you’re a hopeless romantic. Episode 11 with musical artist Tom “The Suit” Forst and episode 22 with Doug Ellin, creator and producer of the 2004 hit show Entourage. You can listen to Cheating: When Love Lies on Podcast One, Apple, Spotify, or wherever you get your podcasts! I hope you enjoy listening and let me know what you think of the show. @SarahBamford_

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