In season five, Kate is offered a job as a music teacher for visually impaired children, while Toby loses his job during the pandemic layoffs. While the job doesn't pay much, Kate has never been happier and more fulfilled in her career. When Toby gets the spot for a San Francisco job, Kate decides to support his decision, and they manage to make it work while also raising their kids, Jack and Hailey. Over time, however, the two begin experiencing distance and being out of sync with one another even when together. They often start engaging in heated spats with seemingly no significant point of contention.
Following a series of many such drifting-apart moments, the two finally reconcile with the saddening fact that they've each grown happier in different directions and may not be what the other person needs. They turn to couples' therapy as their last-ditch attempt to give their marriage a second chance, and when that doesn't help either, the two painfully decide to part ways and finalize their divorce. Though their marriage didn't stay the distance, the two express their genuine gratitude toward one another for shaping them into the better versions of themselves they are today. Both continue to successfully coparent their kids as they move on with their individual lives.
Kate eventually finds love in her music-school boss, Phillip. The two tie the knot in episode 13 as was previously foreshadowed during last season. Kate reveals her future plans to her siblings: that she'd live fearlessly as their mother taught them and open as many music schools for visually challenged people as possible. Toby also meets his person in Laura, who we see him together with during a flash forward as the four of them gather, cheering on Jack's musical performance.
