Finch chooses not to get involved with Nina; Elliot accidentally erases a message on Jack's answering machine.
Jack's upcoming divorce is kept secret from Nina and Finch, who think that he is expecting a baby. When they throw a surprise party to celebrate, the truth comes out. Also, in the wake of her father's separation, Maya tries to communicate better with Elliott.
Nina dates a famous actor who lives with his mother.
Elliot's con-artist brother returns.
Jack has disturbing dreams about the mailroom clerk attacking him. Jack hires Maya's visiting friend as a motivational speaker who in turn confesses to Maya that he outed her as a tattletale in high school and seeks her forgiveness in an effort to overcome alcoholism. Maya attends her high school reunion and, in rebuffing Alan, is debased by another one of his lies.
Finch learns that the beautiful woman he's hitting on is actually a former friend and former male. Elliott tries to help Nina's assistant by convincing Nina that she is related to a big designer, but the lie spins out of control.
Jack has a one-night-stand with Elliot's mother right before Thanksgiving Day dinner.
Jack banishes Finch to work in the mailroom after suffering an insult and Elliot attempts to expose Maya's attractive OB/GYN as a frequent strip club client.
When Maya and Elliott take in a stray dog, Elliott starts to think it is a test to see if he would be a good father. Also, Jack's regular lottery numbers come up a winner, but Finch forgot to buy a ticket for him.
Finch dates a female boxer who has a jealous ex-girlfriend.
Maya and Nina are suspicious when a new employee invites everyone in the office to her bridal shower. Also, Finch teaches traffic school and Kevin's pet tarantula gets loose in the office.
Elliott decides to propose to Maya, but complications arise. After he finally pops the question and Maya accepts, he becomes agitated and collapses.
Maya and Elliott decide not to get married, and she comes to the conclusion that they're not interested in the same things and kicks him out of the apartment. Also, Finch tries to get a porno script of his made.
Nina finds a date for Elliott when he learns that Maya already has one. His date turns out to be a prostitute. Finch is upset when Jack tosses his gift aside.
After learning that the new intern is going to dump his girlfriend in a similar way that she was dumped in high school, Maya exacts revenge on him. Also, Jack and Elliott think that Nina's new magician boyfriend is gay.
Nina's is tricked into attending Sid's bar mitzvah.
Jack worries that Maya's new boyfriend may be her illegitimate brother. Meanwhile, Elliott, who's been living with Finch, wants Finch to get out.
Nina's sister visits from Kansas and becomes very popular at the office.
A romance novelist pursues Finch, offering him gifts for sex. Also, Nina criticizes a disabled actor's shoes on national television, causing an uproar.
Maya picks up a handsome stranger in a bar and sleeps with him, only to learn later that he is the new creative consultant at Blush.
Jack's ex-wife Allie demands a job at Blush in a scheme to try to win Jack back. Her plan backfires when she sleeps with Finch as Jack prepares to walk in on them.