Bree and James both went to St. Joe's High School in Trumbull, CT but at the time, they were just two familiar faces passing in the hallway—Bree a grade ahead, and James quietly hoping to catch her eye. They didn’t know it then, but years later they’d be planning forever together.

Fast forward a few years to the modern dating world: James spotted Bree on Bumble and waited (somewhat impatiently) for her to make the first move, which never happened. Determined not to let the chance pass by, he tracked her down on social media and reached out.

But before things even got started… Bree almost botched the whole thing. It was her birthday (which, fun fact, she shares with James’ dad), so James sent her a thoughtful text: “Happy Birthday! So cool you share a birthday with my dad.” Bree, not realizing who was texting her, thought it was a different JJ from high school and replied, “Thank you so much! So good to hear from you—you and your wife should come to my birthday party!” Understandably confused, James quickly realized she thought he was someone else. But this wasn’t the only time.

A couple weeks later—after a great first date and a growing connection—Bree struck again. James was at his parents’ house watching Sunday football when he got a text from Bree that read: “Hey, I need the deets on James Campbell.” As in… James Campbell himself. Turns out Bree had meant to text a mutual friend from high school, fishing for more info on the guy she’d just gone out with. Very flustered, she called James immediately—laughing and apologizing—while he laughed right along, still trying to figure out what just happened.

Despite the misfires, their first date at Barcelona in Fairfield went off without a hitch. James arrived early and nervously ordered a beer to settle his nerves. Over swordfish à la plancha, shishito peppers, and too many tapas to count, they spent hours talking, laughing, and reconnecting. For Bree—who’s a teacher and not one to stay out late on a school night—something clearly felt different. There was a spark.

Then came COVID. What started as casual hangouts quickly turned into full-blown quarantine together. They spent their days golfing at the par-three course at Short Beach, doing puzzles at the kitchen table, and just soaking in each other’s company—learning all the little things that turn a connection into love. Somewhere between the endless takeout and the puzzle pieces, James unofficially moved in, and they’ve been inseparable ever since.

When it came time to propose, James waited for the perfect moment. He managed to get his whole family down to one of Bree’s family’s classic beach day barbecues in Lordship—no easy feat, and even trickier to pull off without raising suspicion. He only told one person in Bree’s family: her dad.

To get Bree alone, James faked one of his infamous headaches and suggested a walk to help clear his head. As they reached the jetty, he turned to Bree and admitted, “I don’t have a headache”—then dropped to one knee and asked her to marry him.

After a couple of, "are you serious", she said yes.

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The Surfside Hotel