Matt and Rachael matched on the dating app Bumble (yes, really) and quickly began chatting. That conversation led to an invitation to dinner from Matt, and the rest is history. The two met at Leon's Full Service Restaurant in the downtown square of Decatur, GA and followed dinner with ice cream at Jeni's. They enjoyed their dessert outside while listening to a live band play in the center of the square. After, Matt walked Rachael to her car and the two quickly made plans for their second date.

Matt had a birthday at the end of the month and wanted to celebrate at a local steakhouse. Rachael made the reservations a month in advance, choosing to eat on Friday instead of Sunday (Matt's actual birthday is the 30th) as the restaurant would be closed that day and the pair were attending a wedding reception on Saturday. Matt was in Columbus, GA (about 2.5 hours south of Atlanta) for most of the week for work, but came back to Atlanta the evening of Thursday the 27th to officiate the wedding of friends Bill and Lauren Panfel. After filling his boss in on his plans, Matt worked from the Atlanta office that Friday, rather than returning to Columbus, allowing the long-planned birthday celebration to take place that evening. The night of the birthday celebration, Rachael and Matt were preparing for dinner. Rachael was putting the final touches on her outfit before heading out while Matt was "getting the car started." When Rachael walked out of the bathroom, Matt was on one knee! Incredibly surprised, Rachael quickly said yes, giving the couple two things to celebrate at dinner that evening.