Sheltering in place, John didn't deviate from his usual Sunday routine - dinner, 60 minutes, and Hinge. Little did John know, this Sunday would be life changing. After perusing the inventory, John arrives on a striking blonde from USC with a fluffy dog and what looked like an Emmy Award. Intrigued, John fired this blonde cutie a message inquiring how her USC Trojans football squad was looking for 2020. On the receiving end of that message, Madeline nearly declines John's advance but takes her chances with this handsome devil because his hair is just to die for. After a few too many margaritas, Jocelyn Story (Maid of Honor) later convinces Madeline to accept John's invitation to dinner at his place, arguing a man wearing Gucci loafers who lists "Honor Bar" as his favorite restaurant is not likely to be a serial killer. With two wide open social schedules mandated by local politicians, John and Madeline's love was quick to bloom, and the rest is history.

To say Covid-19 complicated things in 2020 is an understatement. John learned this firsthand in trying to propose to Madeline. After a Covid bout in the Littrell family forced him to call an audible on his planned New Orleans engagement, John knew the only place he could propose in Memphis was at Madeline's favorite hotel and wedding-venue-to-be, The Peabody. Days of phone tag with the hotel's skeleton staff left John no option but to enlist the help of his mother-in-law-to-be, Patty, to tie up loose ends. Patty snapped into action and managed to wrangle a photographer and convinced hotel management to allow us to access the roof for a "quick peek at the skyline". All the while, Madeline was completely in the dark and thought that John's idea of staying at The Peabody was so he could see the ducks before date night. On their way to the hotel, Madeline ran the car onto the lawn trying to get out of driveway and John asked "What DO you do well?" Quickly clapping back to John's inquiry, Madeline says "I don't know, you tell me." Well, John had an answer prepared that went on for the better part of their drive. After checking into the hotel, John and Madeline dropped off their luggage and decided to stop by the roof on their way to drinks in the lobby. As they arrived on the roof, they were met with a "Private Party" sign, but this was no deterrent for John. He basically dragged rule-following Maddie past the sign. After arriving at the middle of the roof, John said "I used all my good material in the car, so I'll cut to the chase. Will you marry me?" Maddie (shaking) said yes and John finally dropped to a knee and put a ring on it. After the proposal, John had one more surprise for Maddie - her family was in the lobby of The Peabody awaiting their arrival for a celebratory drink.