Dan finds himself in 1998 following a woman who co-founded a software company, and discovers her fiancé was cooking the books. Meanwhile, Dan's trips disrupt Katie's fund-raiser gala, and the tension only escalates when he admits he sees Livia regularly in the past.

Dan comes to the aid of two brothers traumatized by their father's abuse. Elsewhere, Dan and Livia eavesdrop on an intimate chat between Jack and Katie; and Jack suspects Dan has started gambling again.