It was 2009. We both left our hometowns to come to Chicago to chase our dreams. Te left Pittsburgh to pursue musical theater. Tyler left Minnesota to pursue comedy, and journalism. Tyler saw Te’Shon at a welcome week dance on campus, and thought she was the most beautiful woman there. We later met face to face through our ,mutual friend Cassie, who Tyler knew from doing improv in Minnesota, and just so happened to be Te’s new roommate. We dated briefly, but it wasn’t our time yet. Te broke Tyler’s heart at a Jimmy John’s on campus, but we remained close friends. We would go on adventures in our new city, trying new restaurants and exploring neighborhoods. After graduation, we both went our separate ways. Te got married to someone else, but that didn’t work out. Obviously. Tyler was in a long term relationship that also wasn’t meant to be. We reunited, and went on a second first date. And then a third first date, and that one stuck.

We have a little tradition of doing a Chicago staycation on Juneteenth weekend. In 2023, Tyler planned the proposal all around that weekend – shopping on the Magnificent Mile, brunch at Batter and Berries, afternoon tea at the Drake, swimming in a rooftop pool – and then we went to the Garfield Park Conservatory, where Tyler had scouted out a nice quiet spot by the Lilly pool to propose. Our friends Allie and A.K. were hiding in the bushes taking photos. That night, we met up with many of our friends to celebrate over pizza and drinks.