When Sam sets up his co-worker Milo on a blind date with Robyn, their evening is anything but perfect, as Milo meets his match in a strong-willed, opinionated professional woman with zero tolerance for him. These two would be very happy if they never saw each other again, but the next morning, Sam and Milo discover that she's their new boss.

Milo gets himself in double trouble when he dates a beautiful actress, Michelle, and her alleged twin, Sandy, who are both auditioning for a commercial. To teach Milo a lesson, Robyn tells him that he has to inform one of the ''twins'' that they didn't win the audtion

Robyn hasn't told her mother she's moved from New York to Chicago, so Robyn ''pretends'' to fly to Chicago to visit her mom, only to discover her mother is dating Robyn's old high school boyfriend.

Robyn conspires with Milo to keep Sam---who's been in a slump with women---from learning the truth about which guy in the office a friend of hers really likes. The problem is, he mistakenly thinks it's him.

When Milo discovers that his long-time,''out-of-town'' girlfriend is getting married, he contemplates whether she's the one for him. While on a trip for a charity event, he has a change of heart and decides he wants to stop the wedding, but his Porsche breaks down and he misses his chance.

In 1994 Sam gave to his ex girlfriend his uncle jerome's watch. He is to afraid to go over there and get it cause she is crazy. 4 years later Milo and Sam finally decide to go get the watch. Milo agrees to go get sam's watch if sam gets his TV from his ex. Sam gets Milo's TV but Milo sleeps with Sam's ex and doesnt get his watch. soo Robyn says she will get the watch but the ex (sara)says she doesnt give things back after they are given to her so Robyn goes around her house searching for the watch. She gets a watch but it is the WRONG watch. It ends up that Robyn kept her ex's jacket so Sam decides to try and get it himself. Sam ends up sleeping with her. sara gets pissed cause she fineds out that Robyn, Milo, and Sam are all friends and she throws sam's watch out the window but Leon brings it up and Sam finally gets his watch back.

Milo pretends he's gay in order to get a potential client. But when Milo, Sam and Robyn attend a gay charity event, ""gay Milo"" has to lie about his relationship with Sam, while Robyn, who is trying to impress an old girlfriend, also pretends that Sam is her rich fiancé.

At an advertising awards ceremony, Sam tries too hard to stop his lengthy losing streak; Jack's lifetime achievement award points out Robyn's lack of life experiences; and Milo makes big plans for his expected moment in the sun.

With Jack in London, Sam directs a commercial based on Robin and Milo's disastrous blind date. When Robin starts dating the actor who plays Milo, aka ""fake Milo"" the real Milo pursues"" fake Robin"" only to find out that she too is dating ""fake Milo!"" Robin goes to the airport to meet ""fake Milo"" so they can go away for the weekend. Knowing Robin is about to be stood up, Milo shows up to break the news to her. Meanwhile, after getting a chance to direct, Sam gets an attitude and is detained by airport security. Milo shows his sensitive side by not telling Robin that ""fake Milo"" is a two-timer. Robin then invites Milo to Jamaica with her.

Milo and Robyn end up at the restaurant where they had their failed first (and only) date, but with very different dining partners. Meanwhile, Sam jockeys for a raise from Jack, who has more on his mind than money.