After being introduced by a mutual friend, Rich and Elizabeth agreed to a date. During the outing, a stranger approached the two, noting that Rich definitely liked Elizabeth.
Christina and John started off as friends and coworkers, but realized there was something between them when they started going out on their own, without their mutual friends.
Nina and Hugh met in Montauk, New York. Nina was in town for a friend’s bachelorette weekend and ironically met her own groom-to-be.
Ryan’s move to St. Louis brought him more than professional success. While there, he met Samantha.
Tucker didn’t make the greatest first impression when he awkwardly ran into Sarah at his publicist’s office. Thankfully, he repaired the damage when Sarah attended Tucker’s big show.
Alexandra and Matthew both attended Stamford High School, they didn’t meet until years later, at a party Matthew hosted.
For Felicia, studying paid off in more ways than one. She was hitting the books at the home of her law school classmates when their roommate Dan walked in.
This was a romance a long time in the making. Billy and Elizabeth first met as classmates at Eastern Middle School and became good friends during their time at Greenwich High School.
Drew and Susannah met while vacationing with their families on Nantucket.
Jeffrey and Emma met while working on Ned Lamont’s campaign to represent Connecticut in the U.S. Senate.
When Kate Centofanti and Marc Whittington met during their junior year of college, luck was on their side.
Byron and Courtney’s stars almost did not align. Although they both attended Boston College and had many friends in common, they didn’t meet until the final semester of their senior year.
Catherine McCool and Matthew Leach dated in high school, and although they went their separate ways before college, they remained friends and stayed in touch…
Bradley and Lauren first met at Trinity College in Hartford but did not become friends until they reconnected years later…
Most people aren’t fond of class group projects, but Lindsey Eaton Wood and Matthew James McMaster are thankful for the assignment that brought them together…
In their hearts, it seems Andrea Martinez and Jeffrey Houle always knew what they wanted, even if it took a while for it to happen.
Andrew and Isabella first exchanged glances while attending Cornell, but did not become a couple until they were properly introduced in New York City through mutual friends.
Despite being friends for three years, it wasn’t until they bonded over a shared plate of nachos during a thunder and lightening storm that sparks flew—literally and figuratively.
Even though Juliette and Christian both grew up in Greenwich, they attended different high schools and did not meet until after college when their best friends introduced them.
While studying abroad in Prague, Jamie and Krista found more than just culture—they found each other.
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.
Although Kristin and Richard first met as lifeguards at the Fairfield Beach Club in 2001, it wasn’t until Kristin moved to New York City in 2010 that they started dating.
Ben and Farrell met the old-fashioned way, through mutual friends.
Amanda and Robert met the old fashioned way; a mutual friend introduced them one December night in Westport.
In a way, Wesley and Patrick were both late for their blind date—they just didn’t know it.
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.
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.
Although Hillie and Bernie were in the same graduating class at a very small college, they didn’t meet until they were thousands of miles from home, studying abroad in London.
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.