Season 5

Jack interrupts Nina and Finch. Finch plays hard to get because he wants revenge on Nina. Allie leaves Jack and Maya and Elliott attempt to comfort him.

Nina and Finch don't know about Jack's divorce yet. Jack moves into the Plaza Hotel for privacy. Maya wants Elliott to read an article about relationships but he doesn't, which causes problems. Everybody gathers in Jack's room. Finch and his singing group, 2 Fine, perform.

Nina begins dating an actor who lives with his overprotective mom. Elliott reveals a secret to Maya, who promptly tells the entire office.

Elliott's brother Donnie returns as a successful insurance salesman in need of a loan. Maya, however, remains convinced that Donnie is up to his old tricks, even when he is beaten up. Jack and the rest of the staff discover that silence is not always a good thing.

Maya is reunited with her best friend in high school, Alan, who is now a successful motivational speaker. However, Alan confesses to Maya that he is a recovering alcoholic, but another revelation causes the trouble: he was responsible for her school shunning her. When Maya is unable to forgive him for this, he begins drinking again, disrupting the motivational talk he is to give at the Blush office. Meanwhile, Jack is frightened because of a recurring dream he has about Kevin.

Finch's old friend Bert visits with surprising news--he is now a sexy woman named Brandi. This causes problems for Finch when he becomes attracted to Brandi. Meanwhile, Elliott tries to get Nina to be nicer to her assistant.

The gang gathers for Thanksgiving at Jack's mansion in the Hamptons. Nina is convinced that Jack will fire her for being unhip. Jack sleeps with Elliott's mom, but Finch is convinced that Jack did the dirty deed with his date instead. And Maya just wants to put the perfect dinner together.

Finch is banished to the mailroom after insulting Jack. Elliott tries to prove that Maya's hunky gynecologist is a frequent visitor to strip clubs.

Elliott is convinced that Maya has gotten a dog to test his fatherhood skills. Meanwhile, after his numbers come up, Finch must find a way to tell Jack that he spent his lottery ticket money on candy.

Finch dates a female boxer with a jealous ex-girlfriend. Elliott, Jack and Nina fool Maya into believing that they're smarter than she is.

Elliott goes to traffic school where Finch is his teacher. Nina and Maya debate why they were invited to a coworker's bridal shower. Jack accidentally sets Kevin's pet tarantula loose in the office.

Elliott plans to propose to Maya on her birthday. Nina is being honored in her hometown in Kansas. However, after Nina's plans are cancelled, she interferes with Elliott's plan by tagging along to dinner with him and Maya. Elliott manages to propose, but immediately has second thoughts.

Maya gives Elliott the ring back. Elliott proposes again and passes out again. Maya comes to the realization that Elliott is not interested in what she is and kicks him out of their apartment. Meanwhile, Finch discovers that a porno was shot in Jack's office. After discovering that Nina may be the one behind it, he uses her contacts to get a script of his made.

Jack doesn't like Finch's gift of dog tags. Nina hooks Elliott up with a "friend" for Jack's charity auction after he discovers that Maya has a date already. The "doctor" turns out to be an illiterate hooker. Finch, acting as auctioneer, tries to undermine the auction when he discovers that Jack threw his gift away.

Jack and Elliott think Nina's new boyfriend, magician "The Amazing Zigmund," is gay. Zigmund hits on Elliott--or does he? Meanwhile, Maya decides to enact revenge on her new high school intern after discovering that he plans to dump his girlfriend in the same manner she was dumped many years ago.

Finch is DJing a bar mitzvah. Nina is tricked into attending by the man of honor who has the hots for her. Even after Sid's plan is uncovered, Nina agrees to stay and deal with Sid's advances because Finch leads her to believe he's dying of a rare disease. Meanwhile, Jack and Elliott aggravate Maya when they flip-flop their desire to date a woman based on whether or not they think the other one wants her.

Jack fears that Maya's new boyfriend may be his illegitimate son from a one-night stand many years before. Meanwhile, Finch has been living with Elliott since Maya kicked him out of her old apartment. When Elliott decides that it's time for him to go, Finch goes to long lengths to be able to stay.

Nina's sister Erlene visits New York for the first time from Kansas. Nina becomes jealous when Erlene becomes extremely popular around the office. Meanwhile, Jack is determined to find out who booed him during a speech to the office.

Finch tries to fix his visiting mother up with Jack, in hopes that he can become a Gallo. Elliott tries to help a photographer find his passion.

Finch finds himself a kept man after romance novelist Allison Spencer begins to offer him gifts for sex. Meanwhile, while serving as fashion consultant for the American Film Awards pre-show on E!, Nina criticizes a handicapped actor's shoes, causing a national uproar.

Maya has a one night stand with a guy who says he's a doctor and moving to Spain. However, they're both surprised when he turns up as Blush's new creative consultant the next day. Meanwhile, Elliott becomes obsessed with getting Finch to do a good deed.

Jack's ex-wife Allie demands a job at Blush as part of their divorce settlement. However, she reveals to Finch that it's merely a plan to win Jack back. Plans backfire when Finch sleeps with Allie as Jack prepares to walk in on them. Meanwhile, Nina ruins Elliott's relationship with a therapist.