Everyone in Cedar Cove gets involved in the town’s charity bachelor action as Justine and Olivia scheme to help Grace and Maryellen land the bachelor of their dreams. Meanwhile, Stan asks Olivia to accompany him to see his therapist as they finally deal with past hurts involving their lost son.

Grace finds herself drawn to two different men as Jack worries about Olivia getting closer to her ex-husband. Meanwhile, Seth and Justine take their relationship to the next level, while Maryellen and John grow closer but his secretive behavior makes Maryellen worry that he may be hiding something.

As Olivia deals with the news that Jack may get a job offer that will take him away from Cedar Cove, Grace struggles with what to tell Olivia about the kiss she shared with Will. Meanwhile, Justine helps Warren though a health crisis which causes tensions between her and Seth and Stan’s wife becomes concerned that Stan is growing away from her and closer to Olivia.

As Jack contemplates taking his dream job far away from Cedar Cove, Stan separates from his wife and returns to town hoping to win Olivia back. Meanwhile, Maryellen does some sleuthing to find out what is in John’s past and Grace finally decides to come clean to Olivia about the kiss she shared with Will.

Olivia's brother returns to Cedar Cove with a surprise announcement; Jack considers coming clean to Olivia about his past.

Olivia discovers the new A.D.A. has a deceitful secret; Jack receives a surprising new job offer, but it comes with a catch.

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.

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.