In the midst of personal crisis, four sisters try to maintain their close bonds with each other. Ginnie discovers that she is pregnant and wonders how to deliver the news to her family and husband, Bob.
Ginnie and Bob decide to make a list of things they have yet to experience in New York, which they hope to do before their baby is born, but the act unearths some information Bob has been keeping hidden.
Ginnie causes problems for Anne, and tension among the sisters, when she interferes in her breakup with Danny by trying to reason with him. Rose is mortified when her roommate Flash uses writings from her diary as an acting class monologue. Meanwhile, Marjee contemplates giving up her job as an event planner when she must pretend to be responsible for an error made by her superior.
The Sorelli sisters run their family deli business over the Halloween weekend when Joe goes out of town, but Marjee decides to hold a party at the house, which immediately spins out of control. Anne, meanwhile, discovers that she still has feelings for her old girlhood crush.
Rose’s joy over being selected by her acting class crush for a starring role in a play quickly fades when she learns that the part requires her to be nude. Bob begins to overwhelm Ginnie with his well-meaning micromanagement of her pregnant state. Meanwhile, Anne begins to suspect that Dan hasn’t yet extracted himself from interactions with the other Sorellis, while Marjee ends up living with her boss’ boyfriend.
Rose begins to have feelings for her drama classmate, Alex, and considers losing her virginity to him. Ginnie and Bob are forced to abstain from sex for a short period during her pregnancy. Meanwhile, following an intimate session with her boss' boyfriend, Marjee is awkwardly asked to do a wedding gig with him, while Anne attends the wedding and after a miserable day, finds herself hooking up with one of Rose’s classmates.
The Sorelli sisters remember their mother when they cook dinner at Ginnie and Bob's loft using her old recipes. Meanwhile, Anne is unable to let go of her attraction to Rose's drama classmate, Zach, while Ginnie has an argument with Renee that sends Renee to the hospital with stress-related breathing problems.
Bob buys a car for Ginnie as a surprise, but a disinterested Ginnie's initial reaction softens when she decides to learn how to drive. Rose's new relationship with Alex hits a snag when he asks her if she has feelings for Joel. Meanwhile, Anne worries about her ability to help Joe with Renee's emotional problems after Renee expresses a wish to keep her secrets in her confidence.
Christmas madness kicks in with the Sorellis, as Marjee tries to suppress the growing feelings she has for her boss' boyfriend. Rose tries to figure out whether or not she's going to end up with Alex or Joel. Meanwhile, Bob shocks Ginnie with news that his very reserved parents will be joining them for the holidays, while Anne is caught between her father and the promise of secrecy made to Renee.
Rose goes back to school after the holiday break and decides to make a choice between Alex and Joel. Marjee tells Jason she wants to be with him and hopes he will leave his girlfriend for her. Meanwhile, Anne deciedes to stop feeling guilty about her tryst with Rose's young classmate, while Ginny and Bob's attempt to draw up a will causes friction when the two have conflicting thoughts on who would raise their baby in the event of an accident.
Rose owns up to her feelings for Alex, but worries that she's forever hurt her chances at a friendship with Joel. Ginnie freaks out when she learns that Bob's latest musical project, a sexy female singer, used to be his girlfriend. Meanwhile, Marjee has a hard time dealing with Jason, who won't come clean about her to Trish, while Anne awkwardly tries to get Danny to advise a fledgling food entrepreneur.
Ginnie gets very nervous about Bob's reasons for having his singer ex-girlfriend, Kylie, stay with them in the loft. Rose finds herself confused by Tom's reaction to Alex over their first dinner together with the family. Meanwhile, Anne turns to Marco for advice on men, while Marjee looks to tell Jason her about her own romantic woes.
Ginnie learns that difficulties with her pregnancy will force her to miss Joe and Renee's wedding, prompting Bob to come up with another solution to keep her from succumbing to despair.
Ginnie is forced to go to the hospital with Bob when her pregnancy develops more complications. In the aftermath of Anne and Danny's one-nighter together, the couple tries to assess whether or not to try their hand at a relationship again. Meanwhile, Joel and Jason come to the hospital to help Rose and Marjee cope with the wait over Ginnie's condition.
After losing her baby, Ginnie emotionally retreats from Bob, which leads him to try setting up a special dinner for them. Marjee and Jason set up a business of their own, but find themselves trying to overcome the hurdle of Trish's negative campaign against them. Meanwhile, Joel's new girlfriend begins to bristle at the idea of him rekindling his friendship with Rose, and Anne and Danny attempt to move away from the past and into the future.
Bob balks at Ginnie's attempt to keep a stray dog from the street, hoping she'll take it to a shelter and try to find its owner. Despite her openness with Jason, Marjee tries to deal with her longstanding feelings of being his other woman. Rose discovers her feelings for Joel during a dinner with him and Chloe. Meanwhile, Bob and Anne try to shop for a birthday gift for Ginnie.
Ginnie and Bob decide to take a weekend off with Joe at the Cape in the hopes that they can work through the difficulties in their marriage. The sisters are shocked when Joe announces that he and Renee are moving there for good. Meanwhile, Trish throws Jason out of the apartment, prompting Marjee to ask him to live with her, and Joel gets a kiss from an inebriated Rose which stirs up some tension with Chloe.
The sisters help Joe and Renee make their move to the Cape, and look back over the memories of their mother. Bob is hit with a business trip, but taking it could mean trouble for his already unstable marriage. Meanwhile, Anne comes to grips with the fact that she and Danny may never be a couple again, while Rose decides to make a play for Joel after all, and Marjee has a change of heart about Jason after bringing him into her apartment.