When the Vissers (Jessica's cousins and Ben's friends) arranged a very transparent set-up the weekend of Valentine’s Day in 2015, Jessica was skeptical. Despite the fact that Ben drove a car that looks like a minivan (and still does), they continued talking after Jessica returned home to Maryland. In April, they planned an impromptu trip to Las Vegas with the Vissers, and Jessica stayed in Milwaukee the week after to kick-off her job hunt in the Midwest. When playing White Russian pong (we ran out of beer!) led to a trip to the emergency room for staples in Jessica’s head, Ben suggested the date on the hospital bracelet should mark their dating anniversary. (Ben might have taken the phrase "sweep her off her feet" a little too literally.)

After five and a half years of dating, becoming real estate moguls, learning sign language to communicate with Jessica’s family, buying a house, and adopting a dog together, Ben proposed to Jessica on an early morning walk along Lake Michigan. (It should be noted that Jessica had repeatedly asked Ben to marry her between 2016 and 2020. His response was always: “Maybe when you’re older.”) They celebrated with friends, bagels, and champagne before road-tripping to Maryland to celebrate with Jessica’s family.