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.

A charity baseball game takes place and tensions increase between Jack and Paul as Paul's sister asks about her brother's relationship with Olivia.

Paul cautions Olivia to be leery of Liz and her true motives. Meanwhile, Jack puts his job on the line for Jeri.

Will overstays his welcome at Olivia's home. Meanwhile, Jeri is angry that Jack was offered her job, Paul attempts to go on his first post-divorce date, Rebecca grows exhausted as she tries to prove herself to Paul, and Luke has something to share with Justine.

Olivia gives Paul advice on romance, but her relationship with Jack is plagued by uncertainty.

Jack's past becomes an issue for Olivia. Meanwhile, Jack focuses intensely on work; and Paul makes a surprising announcement prior to Grace's wedding.

Grace and Cliff welcome a big turnout for their wedding. Meanwhile, Paul's unexpected confession requires an important answer from Olivia.