Let's just say if the Red Sox had reached the World Series in 2021, we probably wouldn't be where we are right now. If you know Caroline and Rob, you know these two have a deep love for Boston sports in their veins. Caroline was coming off her first year as a Red Sox season ticket holder and had attended every postseason game at Fenway that fall. When the Red Sox were eliminated from postseason contention, she likes to say she "spiraled" and decided to redownload her dating apps and try her luck. She met Rob on Bumble, a dating app where the girls send the initial message. In line with her personality, Caroline's personality assessment question to everyone became "Astros or Braves?" Thankfully, Rob picked correctly (Braves, of course!) and the two instantly connected over their love of sports. They texted for a couple of weeks as Caroline went back and forth from Florida and Rob was in Massachusetts. They were finally able to talk on the phone on November 11 and planned a date for the following week. Subconsciously, they must've known this connection was special as they both dropped what they were doing to instead meet for drinks the following night at Castle Island Brewery in South Boston. The rest is history!

Rob bought Caroline’s engagement ring in February 2023, hoping to propose later that year. After learning Caroline’s parents were coming up to Maine for a month at the start of summer, he thought this would be a perfect time to pop the question. Rob knows how important Caroline’s family is to her and decided to involve her parents as part of the proposal, making it a special moment for everyone. Over the course of many weeks, Rob began regular communications with Caroline’s parents (in particular her mom) on a daily basis in order to execute the surprise. After setting June 3 as the date to propose, Rob consistently monitored the weather for the week leading up to the proposal and saw that it was forecasted to rain the entire week, including proposal day. He became worried about the weather and would make frantic calls to Caroline’s mom (while hiding in his car – much to Caroline’s concern!) figuring out how to pull off his plan. Fast forward to June 3. Caroline and her mom left in the morning to go get manicures and shop while Caroline’s father and Rob went to work. Rob imagined the proposal taking place on the dock behind the cabins where everyone was staying. The guys planned the set-up on the dock, including rose petals, a personalized champagne bottle Rob ordered (which Caroline had completely missed in her parents’ fridge), and a tarp to cover the slotted dock as everyone has seen too many engagement videos gone wrong after dropping a ring into water. When the big moment came that evening, Caroline and Rob dressed up with the intentions to go to a nice dinner in town where her parents had recently celebrated their anniversary. The weather was holding, so Rob asked Caroline’s parents to take a few pictures of them around the cabins and by the lake to capture their vacation while sneakily sliding an engagement ring into Caroline’s dad’s hands. As they neared the dock, Rob had to pull Caroline through the muck (in her new Michael Kors wedges she might add!), removed Caroline’s other rings from her fingers, and cued her parents to start recording. After reaching the end of the dock, Rob got on one knee and asked for her hand. In total joyous shock, Caroline of course said yes. The two popped their personalized champagne bottle and smiled until their cheeks hurt.