On a snowy January night, Sydney turned down a super enticing offer to go to the Old Shillelagh and instead headed over to a cozy spot by the name of Sid Gold’s where Jack and his friends were bellied up in the back karaoke room in the corner booth. After the hostess sat Sydney and her friend next to the corner booth, the two exchanged looks as he offered the binder that contained the list of songs available. They both went on with their evenings until Sydney heard the buzz words such as “Rick’s American Café” and “University of Dayton”, in no time the two groups had merged and began chatting and watching others go up to sing karaoke. At the time, Sydney wasn’t aware of Jack’s deep appreciation for Tom Petty but that night he bravely sang “Mary Jane’s Last Dance.” Following the night, the two started a friendship that turned into something more when they went on their first date in February at Little Caesars Arena for the Duel in the D. The relationship quickly blossomed as the two both lived a mile away in downtown Detroit and continued to find similarity after similarity, including their shared loved for Polish culture and exploring their city.

A couple months later, the global pandemic hit and the two were required to lockdown together spending almost every moment together, laughing, playing battleship, and eventually organizing a virtual beer pong tournament with their friends. It wasn’t long after they started dating that their lives became intertwined, excited to introduce each other to their friends, family, and family friends. They created a beautiful life together while both living downtown Detroit from joining (and winning) a Come Play Detroit volleyball league to going on countless date nights at almost every restaurant/bar the city had to offer. Jack never fell short in supporting Sydney in her endeavors to pursue her J.D. and M.B.A. at Detroit Mercy that eventually resulted in the two moving to Chicago, Illinois to continually create a beautiful life together in a different area code. The big city definitely had its way of humbling the two, but their love and support never wavered. Going into their third year in the 312, the two have loved each and every moment/opportunity granted to them through friends, family, and experiences.

On December 30th, 2023, Jack got down on one knee in front of the place where it all started, Sid Gold’s. Surrounded by friends and family, they celebrated the engagement where they hung out for the first time, Second Best. Jack and Sydney continue to make lifelong memories at these places, and we hope you join us in continually making lifelong memories at Ivy House come August 2025.