It all started with a Boston girl who needed a little convincing to spend Labor Day Weekend at the Jersey Shore.

In September 2023, just one day before Jill was set to move into her East Village apartment in New York City, she finally took her college best friend, Leena, up on a long-standing invitation to visit the Shore. Less than thirty minutes into a night out, a tall, handsome stranger struck up a conversation. That stranger was Matthew and the two hit it off immediately,

They exchanged numbers, promised to keep in touch, and Matthew even added Jill on LinkedIn (because apparently that's how you flirt in finance). But despite a promising start, their first date would have to wait another six months.

That February, Matthew replied to Jill's Valentine's Day Instagram story, hoping she wasn't celebrating with someone special. Luckily, it was just a Galentine's dinner. He told her to stay single until after his upcoming half Ironman (bold of him), when he planned to finally take her out. As it turned out, after a few back and forth messages on LinkedIn, neither of them was particularly interested in waiting any longer.

Their first date began with Jill bringing along her best friend and roommate, Laurel, to meet Matthew -- which, if you know Jill and Laurel, makes perfect sense. Matthew arrived straight from swim training, with goggle marks still fresh on his face (a detail Jill and Laurel still laugh about to this day). After he succeeded in the crucial test of meeting the best friend, Matthew and Jill set off on their pizza tour of the West Village, followed by a walk along the West Side Highway. They eventually settled onto a bench with a plaque reading "Matt's Bench". A coincidence? Maybe. But it certainly felt like a sign.

From there, they were practically inseparable. Within four months, they'd moved into their first apartment together in Chelsea, where they began building a life filled with their favorite little routines, new adventures, and plenty more pizza.

In January 2026, Matthew proposed at the top of Aspen Mountain. With the Rockies as their backdrop, he got down on one knee, and Jill said yes. They celebrated with champagne and fondue, and began looking forward to their next adventure together.

Now they're counting down the days until they say "I do" in August 2027. The wedding is settled. Whether their future kids will be Red Sox or Yankees fans is not.