Much like many modern day love stories, Alex and Tyler connected by swiping right on a popular dating app. Alex was deep into her first year teaching, and Tyler had recently returned north to begin his season at Essex County Club. The two exchanged messages back and forth before deciding to meet up at a popular spot, A&B Burger. After a successful first introduction, the two spent nearly every spare moment in Tyler's schedule together. In November of 2019, Tyler returned to Naples for his winter season leaving Alex behind in Boston. Though not ideal, the two kept their relationship going into the new year by FaceTiming, calling, and visiting each other when possible. As Alex and Tyler began counting down the days for Tyler's return in April, the Universe had other plans.

The COVID-19 pandemic reared its ugly head mid March, causing the entire world to quite literally come to a screeching halt. Tyler's return to Massachusetts was delayed due to exposure and he was unable to move into the apartment he had waiting for him. Instead, Alex's mom graciously allowed Tyler to move in with them in her home. The three cohabitated during the lockdown as Alex negotiated teaching special education fully remote, and Tyler completed a lot of puzzles as he waited for golf to reopen. In the summer, Tyler was back to work and able to move into his space.

Fast forward to August of 2024. Tyler's parents were in town to visit and had invited Alex's mom to join them for dinner. Alex and Tyler had arranged for a ghost tour in nearby Salem, MA with a group of friends following the dinner. As the group finished eating, Tyler's mom suggested they take a picture to send to Tyler's grandma. As they posed near the water for a picture, Tyler bent down on the ground. Alex screamed as he got on one knee and asked her to marry him. The group celebrated the engagement during their untraditional guided tour of the Witch Trials surrounded by family and friends.