Matt and Olivia reconnected online (on Facebook Dating of all things) after previously going. to UMass Lowell together. However, they didn’t talk to each other ONCE while they were in school. On their first date, Matt and Olivia went to Richardson’s for mini-golf and ice-cream. About 3 hours, of dead-dad jokes, webbed toes, and shared musical experiences, they already started conncecting. Olivia went home fretting that Matt didn’t like her because he didn’t kiss her, but in all reality, Matt was superstitious and din’t want to lose Olivia after one date. Only three dates in, Olivia and Matt had already adventured and Matt was moving Olivia to another apartment. That day, Olivia was singing in the car and Matt looked at her while driving; the song was “All of Me” by Ella Fitzgerald. That was the moment Matt later said he was falling in love with Olivia.

After years of long drives, multiple moves, so many shenanigans, and a growing fur family, Matt and Olivia knew they were each others’ forever person.

To say Olivia waited is an understatement - but, Matt was determined to propose in his own way, on his own timeline. One day during their Falmouth, Cape Cod vacation, Matt and Olivia were on Old Silver Beach when Matt said "Hey, want to go to that winery at 2? It's more of a lunch thing." When Olivia looked at him funny he responded, "Don't think too much about it..." She thought too much about it. After a few tell-tale signs and nice moments at the winery, Olivia spotted Matt's friend Liz with a camera. She said, "Matt, I peeped a camera." to which he replied, "So you know?" Olivia was so excited when Matt proposed that she forgot to say yes! After celebrating and taking some pictures at the winery, Olivia and Matt returned to the Minchello Cape House where family and friends were waiting to celebrate.