Caitlyn and Dakota met as many modern couples do: online dating. After matching in November of 2022, Caitlyn messaged Dakota with a GIF of Billy the Puppet from the SAW franchise, captioned with "Want to play a game?". The two quickly bonded over their love of horror movies, anime, and video games. After a few weeks of Snapchatting and texting, they decided to meet in person for the first time. Both being homebodies, Caitlyn went over to Dakota's house to watch a movie. Dakota insisted that Caitlyn watch Terrifier, an indie horror film that he loved.

This began a series of dates between Dakota and Caitlyn, during which they shared their favorite shows and movies. Caitlyn had him watch Over the Garden Wall, and Dakota, in return, showed her Trailer Park Boys. This back-and-forth went on for several weeks. As they continued to see each other, Caitlyn started to surprise Dakota and his mascot buddies at games. Slowly, she began to develop a love for hockey and enjoyed watching Dakota perform.

Over time, Caitlyn and Dakota attended concerts, haunted houses, and their yearly beach trips. They enjoyed making memories together and trying new things. While at Caitlyn's new home, a small black cat started to come around the house more. Dakota fed the cat daily and gained its trust. Soon after, they jointly adopted the cat and named him Cheesesteak. In the summer of 2024, Dakota officially moved in with Caitlyn.

As Dakota and Caitlyn lived together, they realized they could not live without each other. They discussed getting married, but did not know when. On their third annual beach trip over the Fourth of July, Dakota decided it was time. On June 30th, Dakota was nervous but persevered. They spent time bowling, playing arcade games, and visiting local stores. In the evening, they went to his mother's beach condo, which Caitlyn thought was for family photos. Much to her surprise, Dakota got down on one knee to propose, and she enthusiastically said yes. She was then surprised by her own family, who secretly traveled down to the beach. The rest of the story continues as Dakota and Caitlyn plan their wedding,