The dynamic of Randall and Kevin's rocky relationship is explained. Beth and William spend time together, which unexpectedly brings to light a secret William has been keeping. As Rebecca gets back to work for the first time in years, both she and Jack acknowledge that there is distance between them. Toby is caught straying from his diet regimen, throwing Kate into crisis.

Toby throws a wrench in Kate's weight loss journey. Randall struggles to accept his father's deteriorating health. Miguel and Shelly break some devastating news to Jack and Rebecca, which makes them worry about their own relationship. Rebecca receives an amazing work opportunity. Kevin examines his romantic past.

As Kevin stresses about the premiere of his play, he receives support from an unexpected source. Randall struggles under the pressure of both his work and ailing father. Rebecca and Jack's Valentine's Day doesn't go as planned. Toby and Kate decide to dig deep and get to know each other's biggest secrets.

Jack heads to Cleveland to make things right with Rebecca on the night of her first big gig with the band. Randall, Kate and Kevin make big decisions about their futures.