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…
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''…
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,…
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…
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…
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…
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.
