Tension in the Sorelli family arises when Anne finds out that her sisters are still keeping in close contact with her ex-boyfriend Danny. Bob becomes more concerned about Ginnie's prenantal health and the baby. Marjee is having difficulty on the new living arrangements of her boss' boyfriend. Lastly, Rose gets her first asting gig in a play written by and starring her crush, Alex (guest star Chris Carmack).

While Ginnie and Bob are told to refrain from having sex for a few weeks as a pregnancy precaution, Rose contemplates having sex for the first time as she finds herself really falling for Alex (guest star Chris Carmack). Meanwhile, Marjee and Jason (guest star Julian Ovenden), Marjee's boss’ boyfriend who Marjee recently madeout with, are put in charge of a huge wedding; and Anne winds up sleeping with Rose's classmate (guest star Andrew Keegan) after she spends an unbearable several hours with an awful wedding date (guest star Jonathan Silverman).

With Christmas festivities in full swing at the Sorelli house, Rose is torn between the two men (guest stars Chris Carmack and Kyle Howard) in her life, while Marjee finds herself in unfamiliar relationship territory when she realizes she may be developing feelings for her boss's boyfriend, Jason (guest star Julian Ovenden). Meanwhile, Ginnie is thrown for a loop when Bob announces at the last minute that his parents - most notably his cold-as-a-fish mother (guest star Judith Ivey) -- will be joining them for Christmas, and Anne is put in an awkward situation with her father, Joe (guest star Tom Irwin), and Renee (guest star Christine Ebersole), who is keeping a big secret.

Returning from the Christmas break, Rose must face the two guys (guest stars Kyle Howard and Chris Carmack) in her life and decide which one is right for her. Marjee realizes she can't be the "other woman" any longer and gives Jason (guest star Julian Ovenden) an ultimatum, and Anne (Kiele Sanchez) fully embraces her fling with Rose's 19-year-old classmate, Zach (guest star Andrew Keegan). Meanwhile, Ginnie and Bob sit down with an attorney to draw up their wills, but quickly discover they have completely different ideas of who should be the guardian of their child in the event something should happen to them.

Ginnie learns that Bob is working with one of his former girlfriends (guest star Jaime Ray Newman) at his job as a singer that he's producing an album for her, and Ginnie is not happy. Meanwhile, Anne sends Marco to Danny (guest star Dan Futterman) for a business deal. Marjee forces Jason to tell Trish (guest star Anne Ramsey) they are over before they officially begin their relationship. Rose can’t deny her feelings for Alex (guest star Chris Carmack) and strongly considers losing her virginity to him. Laslty, Rose confronts Joel (guest star Kyle Howard) about his sudden attitude adjustment ever since she rejected him for Alex (guest star Chris Carmack).

With Bob's sexy rock star ex-girlfriend, Kylie (guest star Jaime Ray Newman), staying at the loft, a pregnant Ginnie finds herself jealous and questioning Bob's intentions. Meanwhile, Rose decides to take Alex (guest-star Chris Carmack) home for dinner, but is startled by her father's (guest-star Tom Irwin) strange behavior, and Anne and Marjee commiserate over their boy troubles with Marco (Victor Webster) and Jason (guest-star Julian Ovenden), respectively. The Veronicas (sisters Jess and Lisa Origliasso) perform at Rose's college hangout, Brew Skies coffee house.

After complications with her pregnancy escalate, Ginnie and Bob find themselves at the hospital and more scared than they've ever been in their entire lives. While at the hospital, Annie faces heart-breaking secrets that she never told Danny. Joel comes to the hospital to help Rose through this whole ordeal.

The Sorelli family grieves for the loss of Ginnie and Bob's baby. At the same time, Ginnie distances herself away from Bob as she has a hard time dealing with her loss. Meanwhile, a reunited Marjee and Jason decide to start their own business and manage to land one of Trish’s (guest-star Anne Ramsay) biggest clients, only to find out that Trish had every vendor in town blacklist them.

Also, Rose decides to rekindle her friendship again with Joel, but it proves to be more difficult with Joel's new girlfriend Chloe (guest-star Joanna Canton) in the picture. Lastly, Anne and Dan try to give their relationship another as Danny tries to overcome the secret from Anne’s past while they were apart.

When Ginnie brings home a homeless dog Bob tries to convince her to take it to the pound so it can find its rightful owner. Meanwhile, Marjee starts having doubts and insecurities with Jason as her boyfriend since she used to be "the other woman." Also, when Rose goes out with Joel and his girlfriend Chloe on a friendly dinner together Joel let's Rose know he no longer has feelings for her---but this inevitably leads Rose to figure out her true feelings for Joel. Lastly, Anne does her best to help Bob in finding the best birthday present for Ginnie.

Ginnie and Bob continue to do their best in fixing their current marital problems. The couple decides to spend the weekend at the Cape, with the suggestion of Ginnie's father Joe (guest-star Tom Irwin). Marjee invites Jason (guest-star Julian Ovenden) to move into Anne’s place after Trish (guest-star Anne Ramsay) evicts him from her apartment. Meanwhile, Rose continues to drive a wedge in between Joel and his girlfriend Chloe as she kisses Joel after getting drunk at a college party. Lasty, Joe breaks the news to Ginnie that he and Renee (Christine Ebersole) are planning to make the Cape their permanent home, and a panicked Ginnie calls in her sisters as reinforcements.

The Sorelli sisters prepare to help their father Joe (guest-star Tom Iwin) and Renee move up to the Cape. At the same time, the sisters begin to reminisce about their deceased mother Francesca (guest-star Dana Delany). Meanwhile, Bob is forced to choose between a business trip or staying home and working on his rocky marriage to Ginnie. Marjee also does some heavy thinking as she and Jason begin to move in together. A depressed Anne sturggles over the fact that she and Danny (guest-star Dan Futterman) will probably never get back together. Lastly, Rose decides to stop being the good girl and goes after what she really wants, Joel (guest-star Kyle Howard).