Zack and Maddie first matched on Bumble in mid-November 2021 and went on their first date a few days later. They spent their first date walking around Jamaica Pond and then grabbing coffee at Caffe Nero. Zack ordered an iced coffee even though it was a chilly day and they were sitting outside, which Maddie thought was weird but has since come to realize is par for the course for him. Their date lasted for three hours, during which they bonded over their appreciation for talk therapy, their passion for politics and their shared love of good food and drinks.

After a couple of communication hiccups while they were both home for the holidays, Zack and Maddie reunited in Boston in January 2022 and things took off from there. Over the course of the spring and summer, Zack and Maddie met each other's friends and family members and welcomed the arrival of Zack's first niece in April. In September, they decided to take the next step and move in together. They found a lovely apartment in Roslindale that has been home for the past three years. There, they have hosted numerous parties and get-togethers, have had friends and family visits, and have created a happy and peaceful home. They welcomed a new addition to their home in June 2023 when they adopted Ollie, who joined Maddie's cat Clara to make a family of four.

On December 13, 2024 (Taylor Swift's birthday, for those in the know), Maddie's friend Ruby texted her asking if she wanted to go get drinks at a local bar. Unbeknownst to Maddie, this was a ruse set up by Zack so that he could get the apartment ready for his proposal. When Maddie returned home a couple hours later, all the lights were off and the song "invisible string" was playing on the speakers. Zack had set up three stations in the apartment with candles and part of a letter that he had written. The stations were connected by fishing wire acting as "invisible string," which eventually led to the bedroom door. When Maddie opened the door, Zack and both cats were waiting inside. Zack then asked Maddie to marry him and she said yes. And the rest is history.