Olivia continues to feel uneasy after learning about Jack's secrets. Meanwhile, a charismatic new district attorney and some unwanted visitors arrive in town, and a proposal is made.

Jack pressures Olivia to move in together, but she's hesitant to take this step because she's unsure if she can trust him. Meanwhile, Maryellen comes back to town with a big announcement.

Jack gives Olivia space in the wake of their quarrel. Meanwhile, Justine partners with a rival and a picture proves to be very revealing.

Olivia clashes with Will over a real-estate issue. Meanwhile, Grace is pressured to make a decision regarding her engagement and Olivia and Jack realize that newly formed friendships may jeopardize old relationships.

Paul tries to play peacemaker between Olivia and Will, who have escalated their family feud and are prepared to battle one another in court.