Sara moved back to New England in 2015 to get her master's degree at the University of Rhode Island. Through her grad program, she met her friend Joey, who introduced Sara to many Rhode Island friends. Two of those friends were Greg's now-groomsmen, Chris and Christian. On Halloween 2015, Greg and Sara's mutual friend groups went out to a bar called Dockside in Newport, RI. Although the interaction was brief, one month later, Sara and Greg would get to meet again. Greg's groomsman Chris and Sara were celebrating their November birthdays at Ocean Mist in Matunuck, RI. That night, Greg put his number in Sara's phone as "Greg Winslow So Cute." To this day, it remains Greg's contact in Sara's phone. After the first couple of interactions, Greg and Sara felt the spark immediately and knew early on they were meant to be together. They officially became a couple in March 2016, and the rest is history.

After 5 years together, Greg proposed during a gorgeous sunset at Sara's favorite place, Scarborough Beach in Narragansett, RI. Although Greg thought he was being sneaky, Sara knew weeks prior Greg was planning on proposing. If anyone knows Greg, making plans more than a day in advance is rare, so when Greg asked on a Monday if Sara wanted to get Iggy's takeout and eat it at sunset on the beach on Friday night... let's just say Sara immediately got her nails done and texted her now-bridesmaid Lindsay asking for outfit advice. Greg planned a picnic with Iggy's clam chowder and clam cakes, along with sneaky photographer, now-bridesmaid Alexa, to take pictures. After the proposal, Alexa and Greg surprised Sara with flowers, champagne, and lots of crying and love!