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.