Ryan responded to a prompt Diana had about airport routines (he likes getting to the airport a few hours early to take advantage of the Delta Sky Club, but she was more of a "get to the airport as close to her flight time as possible to avoid sitting in the airport" kinda girl). Hinge conversations led to texts and texts led to their first date on December 9th, 2020 at Raines Law Room in The William Hotel. That first date led to countless more.. and Diana was officially converted to the Delta Sky Club life.

Diana had a long standing Secret Santa dinner planned with her girlfriends in Brooklyn but was going with Ryan to meet his family for a drink in Bryant Park beforehand to celebrate his mom's birthday. After working all day and then going to the gym, where he got ready, Ryan picked her up in an Uber, apparently forgetting all about her Secret Santa dinner and very confused as to why she had a Christmas gift bag in hand. They got to Bryant Park, after lots of crosstown traffic, and Ryan rushed towards the tree, where his family was drinking in the Winter Village. Once there, Diana noticed a large, empty space, right in the direction Ryan was headed, figuring a family was taking a photo there, and so she yelled at Ryan to stop walking... she didn't want him to ruin their shot! When he realized she was calling his name, and refusing to move, he turned and asked her to put down the gift bag. She kept asking, "why?" and explaining how silly it would be to put this gift bag down if his family was just a few feet away, she didn't want to lose the gift! After asking maybe 3-4 times he said "I have to ask you something." That's when it all started to click... and also the exact moment a woman barreled through them, headphones in, saying "EXCUSE ME" in true New York City fashion. He asked "will you marry me?", she repeatedly asked, "are you for real?" and, eventually, gave a big YES. At that moment, she turned to see both their families and their best friends all there with champagne in hand. After photos, Ryan led everyone to a limo where more champagne was drank and toasts were made. When the limo stopped, the surprises continued, though. Ryan planned a surprise party at Lovelace NYC. Turns out, his mom's birthday dinner was never actually happening and Diana's secret Santa dinner took place at 4pm that day instead, everyone was in on the surprise!