Just when the office is starting to fall apart, the Engel's neighbor and well-loved lawyer, Arthur Horowitz, offers Jenna a posh new client - clothing line owner, Harry Le Maire. Jenna must try to impress him, at any cost, in order to keep his much needed business. Ceil and Sandy, also trying to earn some extra cash, start their own dessert company. Meanwhile Jimmy hooks up with the girl of his dreams - his nutty, bad girl neighbor, Irene Horowitz.

Jenna is approached by a former client from her old firm, billionaire software genius Sam Taylor, to handle a merger on his behalf. However, it's the worst time for such a high profile client as Ceil, has infected all the office computers with a virus. In addition, Jenna must also help Jimmy calm down Sandy, who has just been served divorce papers.

When Jimmy gives their grandmother's ring to a stripper, Jenna is forced to intervene to get it back - and makes an unlikely friend in the process. Meanwhile, Sandy wins free mother/daughter hip-hop classes and brings Ceil along, but they quickly realize the class isn't meant for them. Ceil is ready to get out of there, until a former friend makes fun of Sandy, and then Ceil is determined not only that they stay, but that they win the dance competition.

Jenna takes her first case as the new head of the Engel's law firm and Jimmy is all too happy to help out - unfortunately in trying to draw out a confession from their opponent, he winds up sleeping with her. Meanwhile Ceil is at her post "suicide" mandatory group therapy meeting, she has a breakthrough realization - in jumping off the roof, she could have died! And Sandy, who has recently become an ordained minister online, plans a symbolic funeral for Ceil's "old self".

After the accidental suicide attempt of their mother, Ceil, the youngest member of the Engel family, Jenna leaves her job at a big corporate law firm to take over her late father's law practice with help from her sweet ex-con brother, narcissistic mother, and self-help obsessed sister.