Lily and Brendan first officially met in the spring of 2021 at a house party. They hit it off that night, exchanged Instagram follows, and went their separate ways. But fate had been quietly working behind the scenes for years.

Back in 2004, Brendan’s dad was working on an addition at the Connollys’ house. It’s entirely possible that Lily and Brendan crossed paths back then, probably playing football or baseball in the yard—but neither of them remembers!

Fast forward to 2021: after the house party, Brendan casually mentioned that he had met a girl named Lily from Duxbury. By coincidence, Brendan’s dad was once again working on renovations at the Connollys’ house, and Brendan noticed the name "Connolly, Duxbury" on some paperwork. Curious, Brendan asked if the Lily he had just met was the daughter of the Connollys on the paperwork. Turns out, she was—and suddenly, all the dots connected.

That summer, Brendan decided to wait before asking Lily out—he didn’t want things to get awkward while his dad was still finishing the project (although he did pressure his dad at the end to hurry up and finish the job because he didn't want to wait anymore!) Meanwhile, Lily, spending a lot of time at home for the summer, often saw Brendan’s dad and sister, who (along with Lily’s mom) were busy playing matchmaker behind the scenes.

Finally, with just a week left on the renovations, Brendan made his move. On July 21st, Lily and Brendan went on their first date at Florentine Café in the North End. It was the perfect beginning to their story. A few days later, Lily bumped into Brendan’s dad at the house. He asked how the date went, and Lily replied, “It was great—he’s an awesome guy!” They sealed the moment with a fist bump—an unofficial sign that everything was going (and would continue to go) smoothly.

Since then, they’ve been writing new chapters together in their fixer-upper in Winthrop and can’t wait for what’s next.