Sara moved to Virginia at the end of 2017, knowing only her friend from college and now roommate Holly. Holly dragged Sara to an ugly Christmas sweater party and there she briefly met Kevin. Sara then hung out with Kevin and his housemates a few more times in group settings (Brunch, New Year's Eve party, Onesie party). Finally, in March 2018, Sara and Holly hosted a dinner birthday party for Holly's now husband Rich, and invited Kevin and his housemates. Some say it was Sara's cooking that convinced Kevin to finally ask Sara out to dinner. They went to dinner, started talking, and all of a sudden they realized they had been talking for several hours and were the last ones in the restaurant. They've been talking and eating together ever since.

Kevin convinced Sara to take their dog Bailey on a hike that was recommended by a coworker (a lie). The hike brought them to a little pavilion overlooking a picturesque lake/swamp. As they approached the pavilion, Sara saw flower petals arranged in a heart on the ground. By the time it dawned on Sara that they were for her, Kevin was already on one knee proposing. Sara of course said yes. (Meanwhile, oblivious to the momentous occasion, Bailey was busy running through the perfectly curated flowers). Bailey then helped retrieve Kevin's sister Grace (the flower architect) from her hiding spot take pictures.