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The series begins with the four Sorelli sisters in the midst of their very complicated lives together. Oldest sister Ginnie, a high powered attorney is having difficulty on telling her husband that they are having a baby. Ann (guest star Laura San Giacomo) is dealing with the fact that her longterm relationship with her boyfriend Danny (guest star Jon Hamm) may be over. Marjee is in a rut on finding a restaurant to host a Pug Dog Benefit featuring Jillian Barbaree that will have live dogs. Also, college student Rose is having a hard time telling the family that she has switched college majors from Pre-Med to the Experimental Theatre Ring. While all the sisters lives are in a rut they also have to plan their father's engagement party as he is remarrying to a woman that they don't particularly care for.

The series begins with the four Sorelli sisters in the midst of their very complicated lives together. Oldest sister Ginnie, a high powered attorney is having difficulty on telling her husband that they are having a baby. Ann is dealing with the fact that her longterm relationship with her boyfriend Danny (guest star Dan Futterman) may be over. Marjee is in a rut on finding a restaurant to host a Pug Dog Benefit featuring Jillian Barbaree that will have live dogs. Also, college student Rose is having a hard time telling the family that she has switched college majors from Pre-Med to the Experimental Theatre Wing. The sisters are also dealing with the fact that their father, Joe (guest star Tom Irwin, "My So Called Life"), has just announced plans to marry his girlfriend, Renee (Christine Ebersole, Tony Award winner for "42nd Street"), a development that has left the women with conflicting emotions.

Ginnie and Bob pretend to be tourist for a day and travel all over Manhattan as the couple decides to make a list of all the things they want to do in New York City before the baby arrives, but the task reveals a secret that Bob has been keeping from his wife. Marjee is clashing with her new father Joe (guest star Tom Irwin) step-mother Renee (guest star Christine Ebersole) as Marjee moves back in with her father and Renee after being evicted from her old apartment. In the other Sorelli sisters' lives, Ann agonizes over how to handle her emotional break-up with Danny (guest star Dan Futterman). Rose develops a crush on one of her classmates in actiong class, Alex (guest star Chris Carmack). During an acting seminar he manipulates her on stage as part of their assignment and embarrasses Rose. Alex tries to invite her to a party but rejects his offer due to her embarrassment. Rose gets some advice from her friend Joel to see if Alex is really into her.

Ann continues her sad moodiness over her break up with Danny (guest star Dan Futterman) as she's staying home in her sweats and getting rid of old furniture---particularly her matress. She thinks it's cursed. Ginnie feels she needs to talk to Danny as she's still in a lot of pain over her relationship ending, but this causes some serious tension between the sisters. Marjee is having a hard time with her boss (guest star Anne Ramsey) as she's making her take the fall for a lot of the party planning mistakes that she didn't do as well as medicore chores on staff assistance. Marjee eventaully considers quitting One of Rose's classmates, Zach befriends Ann despite their age difference. Flash (guest star Shanola Hampton) goes too far in one of her monologues in acting class when she mimics Rose's college life through a fake journey and makes fun of her. Rose then goes to the NYU Housing Office to find another room to get away from Flash, but is unsuccessful. Rose finds out Flash's real name---Tiffani Lusinski.

With their father (guest star Tom Irwin) out of town for the Halloween weekend, the Sorelli sisters agree to hold down the fort at the family deli, but things get a little out of hand when Marjee decides to throw a huge party at the house. In the midst of the chaos, Anne realizes she still has feelings for her childhood crush, Marco (guest star Victor Webster).

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 a family Thanksgiving planned in Ginnie and Bob's loft, Ginnie, Anne, Marjee and cook a traditional Sorelli dinner using all of their mother Francesca's (guest star Dana Delaney in flashback scenes) favorite recipes. The sisters also reminisce about memories of their mother. Meanwhile, Anne is frustrated over her feelings for Rose's classmate, Zach (guest star Andrew Keegan, “7th Heaven”); and Renee (guest star Christine Ebersole, Tony Award winner for “42nd Street”) is rushed to the hospital with a stress-induced asthma attack after Ginnie blows up at her.

After forcing Bob to return the car he bought as a surprise for her, Ginnie has a change of heart and decides to have Marjee teach her to drive instead. Rose's new relationship with Alex (guest star Chris Carmack) hits a bumpy patch when he questions whether Rose's best friend, Joel (guest star Kyle Howard), has feelings for her; and Anne quickly realizes she may have bitten off more than she can chew when her father, Joe (guest star Tom Irwin), asks her to help his emotionally troubled fiancée, Renee (guest star Christine Ebersole). Rose questioneds her sisters about her realishonship with Alex

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.

Ginnie is devastated when her doctor informs her that pregnancy complications will prevent her from attending her father’s (guest-star Tom Irwin) wedding to Renee (guest-star Christine Ebersole), but Bob devises a plan to keep the family together. Anne encourages her ex-boyfriend, Danny (guest-star Dan Futterman), to come to the wedding even though she is taking Marco (guest-star Victor Webster) as her date, and Marjee is furious that Renee’s son (guest-star Peter Paige) ruined the sister’s surprise wedding gift by announcing his gift first. Meanwhile, Rose and Alex (guest star Chris Carmack) decide to ignore a strict drama school policy and audition to be movie extras in a local production

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).