Weddings

Paige Cynthia Corbin & Tyler Gebert Kyle

On Halloween, a day typically filled with tricks, Tyler and Paige got the best treat of all—an introduction to one another by Tyler’s brother. The two bumped into each other a few times afterwards, but it wasn’t until a chance meeting at the Surf Lodge in Montauk that they began dating.

Weddings

Whitney Young & Tobias Crawford

When Whitney Young moved to Boston after finishing graduate school, a friend suggested she get together with Tobias Crawford. Though they just met for coffee, they soon arranged a proper date. Two years later, during a hike at World’s End in Massachusetts, Toby proposed.

Weddings

Maria Louise Calise & Jon O’herron

Maria Calise and Jon O’Herron became acquainted about fifteen years ago. Jon would grab lunch from Calise’s Food Market, a local mainstay owned by Maria’s sister and brother-in-law. One snowy evening, the pair ran into each other at Dunville’s and struck up a conversation, which ended with a plan for their first date at Positano’s.

Weddings

Maureen Elizabeth Keough & Philip Rousseau Epifano

Fate is a funny thing. Just ask Maureen and Philip. Although their older sisters are childhood best friends, and Maureen’s brother was on the same soccer team as Phil, the couple didn’t meet until a mutual friend’s wedding at the Burr Mansion.

Weddings

Rebecca Shaw & James O’Callaghan

Though Rebecca and James were friends at New Canaan High School, they parted ways for college before reconnecting again in New York City, where their relationship began. Wanting a hometown proposal, James brought Rebecca to Waveny Park and popped the question.