In the Season 5 premiere, Sonja kicks things off with a party to mingle with Aviva, Carole and Heather. They all seem to hit it off. . .until Ramona arrives. And as they say, with new friends come new revelations -- in this case, Aviva learns that a couple of her "new" friends have had relations with her ex-husband. Meanwhile, Heather and Carole try to figure out who to trust and not. Picking up right where they left off, LuAnn is still annoyed with Ramona about the disparaging comments she made about LuAnn's parenting (from last season) and tries to discuss it with her at the party, but Ramona has no interest. Things get interesting as Sonja, Ramona, Heather, and Aviva head to the Hamptons for the weekend and once back in the city, LuAnn surprises the new ladies with a shocking story. The three new women agree to never become "mean girls."

Uptown ladies Aviva, Heather and Sonja take a trip downtown to Carole's cool neighborhood where she hosts an afternoon of brunch, booze, and bitching that includes New York's most popular ex-husband, Harry, Carole's commitment phobia, and Aviva's fear of just about everything else. With her townhouse falling in on her, and no settlement in sight, Sonja attempts to take charge of her financial future by launching a catering company. Always hard at work, Heather decides to mix business with pleasure and invites SOME of the ladies to join her on her next business trip to London. Things get interesting when the ladies come together to celebrate a jewelry launch and Ramona takes the opportunity to apologize to Heather but gets a cold shoulder from LuAnn, who might not be ready to bury the hatchet.