After a handful of witty quips via Bumble, Drew & Evonne decided to meet up after Drew got back from a trip. Drew picked the Owl's Tail: a cute cocktail bar on the Upper West Side for their first date the day before Thanksgiving 2019. After they had a great conversation about every popular TV show, laughed over Drew's appreciation of the sheer magnitude of Evonne's reading goggles, and one-upped each other with similar travel discoveries, they were treated by a couple of strangers to an impromptu Bob Dylan concert at the Beacon. Right when Bob finished mumbling his second song, Evonne nestled her head onto Drew's shoulder and scooted close enough for him to get his arm around her. With one hand around her shoulder and the other hand underneath the arm of the chair interlaced within Evonne's, it was instant sparks. To no one's surprise, it was love shortly thereafter.

Riverside Park is special to Evonne and Drew because it is where they have spent countless hours running, walking their favorite dog Bogart, and marveling at the changing of the seasons together. The 91st Street Garden is the most special place within that park because it is where the majority of Drew's & Evonne's runs together would end and where Tom Hanks (and Brinkley) revealed himself to be Meg Ryan's true love in the 1998 Oscar winner for Best Picture "You've Got Mail." For this reason, Drew planned to take Evonne for a run through Riverside Park, ending at the 91st Street Garden, to complete a virtual family Turkey Trot on a rainy, Thanksgiving 2020. Once they trotted, they stopped at the 91st Street Garden to catch their breaths. Drew mustered up the courage to get on one knee and ask Evonne to marry him. At first, she thought he was playing a joke on her, then with the ring on her finger, she realized this was the real thing. 37 minutes later, she said "yes."