Magazine owner Jack Gallo makes peace with his estranged daughter when she asks him for monetary help--and lands a job at the mag.

Maya's life becomes a nightmare when her co-workers discover that she's had a sex dream involving Elliott.

Jack has a slight problem with Maya's new boyfriend- he's the same age as Jack. When he voices his disapproval to Maya, she accuses him of being hypocritical, since he married someone her age. Both parties are left with a personal dilemma. Jack wonders if he is in fact being hypocritical, and Maya wonders if she may be dating the man to get back at Jack. Meanwhile, Nina's flirtation with a window washer proves hazardous to his health.

Maya's fantasy piece about a dinner with Woody Allen brings notice from a lot of people--including Woody Allen himself, supposedly. The man who shows up at Maya's office the next day is not Woody Allen, but he presents himself as such, and actually seems to believe he is. Maya finds herself playing along with the charade until their relationship and her life turn into her favorite movie, Annie Hall. Meanwhile, a mix-up over eyedrops causes Jack to temporarily lose his sight.

Jack and Finch discover a pneumonic-message system in the wall. Meanwhile, Elliott invites Maya to his house for his ""slow"" brother's birthday party. At the party, Donnie reveals to Maya that he's not really ""slow."" Maya tries to tell Elliott that Donnie's not stupid, but just ends up looking silly herself. Jack's inanity causes Donnie to reveal his act. And a gift of a parakeet explodes into a living nightmare for Nina.

Nina is throwing a Halloween party! At the party, Finch and Elliot compete for Blush's newest cover model, Kelly. In the end Finch gets her, only to find she is a lesbian who thinks he is a woman. Meanwhile, the jealous Elliot tries to keep Vicki from going home with a guy she met at the party.

The outrageous behavior between Finch and his sexy partner (Gina Gershon) galls Maya, who sets out to rein in the stallion. Also: Jack and Maya compete for an office-cleaner's favor in a feud that gets way out of hand.