Finch returns from Jamaica after a failed attempt at romance with Courtney, who played him, as it turns out. Elliott steps in to try to prove what a friend he is to Finch by giving her a dose of her own medicine--getting her hooked on him and then telling her to kiss off. Unfortunately, the plan goes awry when he ends up liking her and they start dating for real. Meanwhile, Jack makes another bet with Donald Trump--whoever loses less weight has to wear a dress during their golf game. However, he makes the mistake of asking Nina for help with his diet.

The episode was rated 7.41 from 27 votes.

The staff prepares for the annual softball game against the magazine Cosmo. Jack hires Steve Garvey, so that he can play on the team. Maya turns out to be a great pitcher but becomes too competitive.

The episode was rated 7.41 from 22 votes.

Maya decides that since the new Miss Pretty column is so good, she will do a column on Miss Pretty. Finch then informs her that the new Miss Pretty is actually a man, but Maya thinks that will make the article even better, and insists on meeting him. The trouble is that Miss Pretty is actually Finch himself-and he is determined to keep the office from discovering it. He tries to escape from the mess by hiring professional scam artist Kurt to pose as Miss Pretty, but things only get worse when Maya falls for him. Meanwhile, Nina finds herself roped into an unwanted friendship with a woman she can't stand, and Elliott and Jack find themselves in hot water when they accidentally insult an Asian-American executive from an important advertiser

The episode was rated 7.43 from 28 votes.

Nina gets into a catfight with modeling rival Margo Langhorne, then becomes upset when Margo decides to retire from modeling. Jack is upset that Donald Trump has a sandwich named after him and gets Finch to attach his name to a park. Maya's new boyfriend enjoys taking his shirt off in public. And Elliott's wearing new shoes to please his girlfriend, but they only make him slip.

The episode was rated 7.44 from 27 votes.

Jack vows to get in shape after throwing his back out playing with Hannah and hires a personal trainer who used to be a Navy SEAL. Meanwhile, Finch and Maya collaborate on a screenplay, leaving Elliott out in the cold.

The episode was rated 7.50 from 28 votes.

The nominations for the annual Femmy awards are in and Maya, Nina and Elliott are nominated, while Finch isn't even invited to the ceremony. Jack switched Maya's nominated article and nominated a picture of Elliott's that was actually taken by a chimpanzee. At the dinner, Finch scores a seat at the models' table while Maya and Nina prepare speeches. Elliott is going crazy with guilt until he loses. Nina wins after 12 straight years of losing. Maya wins for the article, which Nina trashed in her acceptance speech.

The episode was rated 7.52 from 25 votes.

Finch is very frustrated when an old nemesis, Barry, shows up one day to gloat over his success. Not only does Barry own a successful business, but he is also engaged to their high school homecoming queen. Finch agrees to a double date with Barry and his fiancée, and he wants desperately to show Barry up by scoring a better looking date. He finds his answer in the form of Adrienne, a gorgeous supermodel. Adrienne would normally be way out of Finch's league, but by manipulating her many insecurities, he makes her fall for him. However, he still has one more obstacle to overcome-Adrienne's ex-boyfriend has decided he wants her back. Finch is forced to take desperate action if he wants to hold on to her, and does-he asks Adrienne to marry him, and surprisingly enough, she says yes. Meanwhile, Jack makes plans to have his photo taken in front of a new painting in his office, but unfortunately, he doesn't realize that the painting depicts an obscene act.

The episode was rated 7.54 from 24 votes.

Maya's attempt to host a murder mystery party is plagued with problems. Elliott wants to ditch the party for an Armani gala being held on the same night, Nina shows up with Maya's old boyfriend Derek, Jack wants to wear Elliott's costume, Finch is trying to make time with the caterer (who is dressed as a large-bosomed French chambermaid), and gamemaster Larry is a down-on-his-luck actor who spends most of the party on the phone with his agent. Everything is thrown into chaos when Maya's next door neighbor suffers a heart attack and drops dead -- and everyone but her thinks it's part of the game.

The episode was rated 7.55 from 22 votes.

When Maya's first love John Kenny pops back into town, she becomes as happy as she's ever been, as the two find their old spark back in full force. However, Jack is angry about the whole thing, as he still has not forgotten when he walked in on the two of them fooling around one time. Maya then learns the true horror of the situation- the only reason they were separated in the first place was because Jack had pulled strings to get him into the Royal Shakespeare Company, and she becomes instantly fearful that he will once again begin to interfere with their relationship. Meanwhile, Finch uses a "tough love" method to train a new intern while Nina's television appearance is ruined when an old allergy acts up.

The episode was rated 7.58 from 31 votes.

Jack wants the tenants on the floor above Blush to move. Maya is taken in by Finch's lie that he wants them to move so he can build a free daycare center. The real reason: a steam room. Meanwhile, Nina meets with her former model roommate, who is now fat.

The episode was rated 7.59 from 27 votes.

Jack enlists Finch to stop off at his house and check up on his new nanny. However, Finch ends up having sex ("Twice!") with the nanny. But his joy may turn to embarrassment after he discovers Jack had a hidden camera installed in the room that they used. Meanwhile, Elliott neglects a favor Maya asked him to do, and Nina joins a cult.

The episode was rated 7.65 from 34 votes.

Finch is convinced that a model likes him, only it turns out that she likes Maya instead. He sets out to create the ultimate male fantasy: watching two females go at it. All is going well for Finch, until Maya finds out and the two females decide to turn the tables on him. Meanwhile, Elliott and Nina go overboard in their insults after Jack tells them that he just wants to be one of the guys.

The episode was rated 7.79 from 24 votes.

As a prank, Finch switches the cards on two of Elliott's birthday gifts: those from Maya and Persky. As a result, Elliott believes that Persky has given him a really cool video game system, and Maya has given him a box of kinky sex toys. When Maya invites him over that night to have some fun, he naturally gets the wrong impression, and is forced to give his relationship with her some deep thought. Meanwhile, when the racehorse Jack bought with Robert Goulet acts up before the big race, he enlists Nina's aid to calm it down.

The episode was rated 8.00 from 25 votes.

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.

The episode was rated 8.00 from 33 votes.

Halloween is no treat for Maya when Finch gets her to wear an embarrassing costume to the office. Luckily, she meets her Prince Charming in an elevator. Meanwhile, Jack confesses to a dirty trick he played on a young impressionable Maya; and Elliott and Finch hatch a plan to find out if Nina's friend Binnie really exists. Finally, Finch claims he wasn't the least bit scared by Alfred Hitchcock's horror masterpiece Psycho, so Elliott sets out to prove he's lying.

The episode was rated 8.04 from 25 votes.