10. 02. 2026

When both Kristen and Tom were ready to give up on dating apps, they each decided to give it one last shot. Kristen almost canceled their first date, but her roommate Sydney urged her to go—“you never know, he could be the one.” That night at Parla in Assembly Row, Kristen and Tom discovered they had both been at the same Zach Bryan concert in Worcester just weeks earlier. The connection was instant. One date turned into another, and before long, Tom was asking if he could introduce Kristen as his girlfriend to his friends at the Red Sox vs. Mets game while celebrating his 28th birthday. A year later, Tom had moved in with Kristen in Medford. During their relationship, Tom took Kristen away a few times to the Cliff House in Maine, which quickly became one of her favorite places. So when it came time to propose, Tom knew there was no better place. On a perfect July day, he surprised Kristen at her parents’ house in Maine, whisked her away for a weekend at the Cliff House, and later that evening, asked her to marry him.