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Francesca Mascola

and

John Oliveira

September 25, 2026

The Wadsworth Mansion, Middletown, CT
88 days88 d4 hours4 h21 minutes21 min21 seconds21 s

How We Met

Every great love story starts somewhere…

It all began at a local bar called Hard Hat, where I worked and where our mutual friend (and now honorary cupid) decided to set us up. That night, said friend texted him to come down and meet me—he showed up, eager, bold… and maybe just a little overconfident thanks to a few drinks. Let’s just say, first impressions weren’t exactly smooth. I was not impressed. In fact, I was pretty sure that was the end of that. But life has a funny way of circling back when it's meant to. We crossed paths again, and he completely redeemed himself. We laughed off that wild first encounter and went on our very first real dinner date. Now here we are—proof that sometimes, even a rocky beginning can lead to the most beautiful story. And yes, we still laugh about that night at Hard Hat.

How He Proposed

Let’s just say… it was not your typical fairytale setup—but it couldn’t have been more us.

It was a regular Monday afternoon. I was off from work, lounging in my favorite sweats, waiting for him to come over. He was slowly moving into the in-law apartment I had renovated, and that day he was bringing over a few last things. Nothing fancy. Just a dog walk on the agenda. He showed up in his LA Chargers sweatshirt, casual as ever, and handed me a card and a bag of chocolates—he said it was an apology for making me drive him all over the weekend before when he lost his keys (classic). I opened the card, read his sweet note reflecting on our journey from Hard Hat to here, and laughed—thinking, aww, cute! But he just looked at me like… “That’s it?” Then he told me to open the chocolates. I wasn’t in the mood—I was focused on the dog walk! But he insisted. So I finally gave in and opened the bag… only to find an empty jewelry box inside. Cue shock. Right then and there, in the middle of the living room—no grand crowd, no cameras, just us (and the dog)—he got down on one knee and asked me to marry him. It was unexpected, imperfectly timed, and absolutely perfect.

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