HINGE! Lesley was burnt out on the app dating scene and John was just entering into that world. They met at one of Lesley's favorite spots in the Lakeview neighborhood of Chicago, Wilde, an Irish pub with a literary-theme, and immediately hit it off. Lesley was shocked that John, who grew up in Chicagoland, had never experienced the Mariano's bar (the grocery store down the street with the best happy hour deals and bar vibes in the city, in Lesley's opinion) so she insisted he experience it on their first date. The rest of the night was filled with making friends with strangers, greasy pizza, darts, and their first kiss.

It was peak pandemic time in November 2020. John added a date night to their shared calendar, but didn't note the location and told Lesley it was a surprise. The day of their surprise date, Lesley took some extra time getting ready and had a tiny thought that maybe he was proposing, but quickly brushed it off and dismissed taking the time to do her nails. John drove them to downtown Chicago, where they don't frequent much for date nights, and they made their way to the rooftop of The Gwen, a luxury hotel. They were seated in a secluded couch on the rooftop, with personal blankets to keep warm. John disappeared for a moment and when he returned, he sat down, looked at Lesley, and said, "I can't hold it in anymore" and divulged into a sweet speech that ended with him getting down on one knee. One of his best friends who lives out of state, Alison, appeared from around the corner filming the entire thing, to which Lesley reacted by saying, "You're not supposed to be here!" The rest of their night concluded with celebratory drinks, telling family, and enjoying their time at The Gwen.