Kelli and Tom started talking when they matched on a dating app on January 31, 2021. Both Kelli and Tom are corporate nerds and love Microsoft Excel - so much so that they both had on their dating profiles how much they like to create spreadsheets as a fun fact. The algorithm of Hinge brought Kelli to Tom's profile. Kelli "liked" one of Tom's photos and Tom decided to message Kelli. They chatted via texting and realized they both had the day free and decided to go out that same day.

Their first date was at Providence Oyster Bar on Federal Hill in Providence. Tom insisted on booking the reservation and Kelli asked specifically if they could have the high tops (foreshadowing Tom's chivalry and Kelli's specific taste). Kelli was 10 minutes late to the date and stepped on Tom's foot when she went to give him a hug.

Despite the rocky start, they sat at the restaurant for over 3 hours - getting to know each other and sharing Allagash White beers and appetizers. Surprisingly, they talked about many other things besides spreadsheets. Not wanting the date to end, Kelli suggested they go to Pastiche and get dessert. They had to eat in Tom's car since it was during pandemic times. On the way to the car, Tom spilt his hot chocolate drink all over his shoes. They went on their second date two days later and have never missed a day of talking to each other since.

On March 25, 2024, Tom proposed to Kelli in the living room of their Cranston home surrounded by all of their closest friends. They had often hosted "Bachelor Finale Parties" in the past, so he organized a party to watch the Bachelor Finale, with everyone in on it being a surprise engagement. Tom put on his suit and proposed to Kelli (who was in her sweatpants), with a red rose ring box and asked if Kelli "would accept this rose". She said "yes, yes, yes, yes, yes!" and the rest is history.