Nate and Alyssa met through the dating app Hinge, with a shared location of Chicago, IL. Little did Alyssa know, Nate was actually in the apartment hunting phase - and still lived almost 500 miles away in Pittsburgh - at the time they matched on the app. After exchanging some messages, Nate had to admit he was waiting to ask her out until he actually lived where the app said he did. Once he moved, he asked her out the first weekend he was officially a Chicago resident. The couple shared their first date at Lucky Strike, a bowling/arcade restaurant, played games, and chatted for hours. It was clear the attraction was mutual. The two officially became boyfriend and girlfriend on March 12, 2023.

After a couple "fake proposal" dates to throw Alyssa off the scent, Nate officially proposed on July 31st, 2025 in Lincoln Park. The couple shared a picnic together and after setting up the blanket and food in the grass, Nate asked to set up his tripod so they could take a photo to capture the dinner in the park. Hidden inside the tripod case was the engagement ring! The two were able to share an intimate, romantic moment together on a perfect 70º summer day in Chicago with lush greenery surrounding them and the sun setting.