Andrew and Natalie met on a boat. It was July 5, 2019, on a booze cruise on Lake Michigan. Natalie had recently moved to Chicago and was exploring things to do in the city, excited about meeting new people. Andrew was celebrating his sister’s birthday with siblings.

Natalie had initially made friends with Kate, Andrew’s sister, who made the introduction. By the end of the day we realized there was something that clicked and we ended up going on a date the next weekend.

The first date was weird. We met for brunch at Happy Camper in Old Town, and were both so nervous we didn’t even eat. Then Natalie surprised Andrew with tickets to a rooftop day club on the river that turned out to be a singles mixer. We definitely didn’t belong, but we were there together, so we spent the entire afternoon making fun of the absurd situation unfolding around us and rolling in fits of laughter. We didn’t know it then, but this would be the dynamic we’d carry forward for the rest of our relationship.

Over the next few months we spent most of our time getting to know each other while people watching at Butch McGuire’s or laughing at the comedy series I Think You Should Leave. We were getting pretty serious and were splitting our time between Natalie’s place in the Gold Coast and Andrew’s in North Center until March 2020.

When COVID hit we found ourselves hunkering down in the same apartment, which certainly had its challenges. But it was also a turning point in our relationship. This was the period when we really came together as a couple. Through all the uncertainty and Zoom calls and Animal Crossing, we built a life together, and fell in love.

In May 2022 Natalie brought Andrew to Italy. It was Andrew’s first trip overseas and Natalie, having been to Italy several times, was beyond excited to show Andrew around. On our second day of the trip, as we sat sipping our morning espresso on the private balcony of our Airbnb in Rome, Andrew got down on one knee and asked Natalie to marry him. Somehow, Natalie was caught by surprise, and she said yes!