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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).