Kevin

Kevin is an old friend of Lolly Lavigne from North Carolina.

History
As teenagers, they took summer jobs together and got into a lot of trouble.

Original timeline
In the "original timeline", Kevin met Becca Brady in 2003 when he moved to New York for his start-up. Lolly, who was still hung up on her feelings for Kevin, introduced them. After a chance meeting, the pair began hanging out. They bonded and grew closer until eventually, he and Becca slept together. All the while, Becca was still married to her husband of eight years, Sean Reeves. Kevin and Becca professed their love for one another and planned to run away together. For this, Becca decided to divorce Sean and tell Lolly about them. However, when Lolly got angry about the revelation, Becca decided to end things with Kevin.

New timeline
In the timeline where Becca was sent back twenty years in the past, from 2015 to 1995, Kevin encountered Lolly during a trip to North Carolina for an R.E.M. concert (one they never went to in the original timeline). During their brief reunion, Lolly invited Kevin to visit her in New York. Kevin obliged and, some time later, arrives in New York with the intent of only visiting and staying for a few days. As fate would have it, Becca is still roommates with Lolly at the time and thus meets him eight years too soon. Just as they did in Becca's original timeline, the pair hit it off when they started talking, which did not immediately happen as Becca tried to avoid him his first two weeks in the city. When they did, however, Kevin seemed smitten enough to decide to stay in New York for a little while longer, saying he'd "fallen in love" with New York.