Jake agrees to a date with Naomi's sister, Kylie, but things don't go as planned when he realizes they've met before, a fact that Kylie remembers in great detail but which Jake can't for the life of him even recall. The date gets even stranger when Kylie's ex-boyfriend, Patrick, a performance artist in the style of David Blaine, drops in - literally. Meanwhile, Jake's best pal, mild-mannered dentist Adrian, gets inadvertently stuck babysitting one of Jake's star clients, Shane, a macho action star with more than a few issues.

Jake faces a PR crisis when one of his top clients, Dakota - part of the three "Gaymigos" design team, wants to go public with the fact he's straight. Meanwhile, the girl Jake's romancing insists he set up her unhappily single cousin with a date, and the only guy he can find is Patrick; and Adrian's in-laws turn up and insist on seeing their favorite person - Jake!

Jake drives himself crazy trying to one-up his biggest rival, super publicist Peter Beth, and he thinks he's finally done it when he convinces a glamorous actress to be his date for Peter's birthday bash. Meanwhile, when Patrick finds out that Peter is David Blaine's publicist, he's determined to crash the party.

Jake gets caught up in his client's love life when an actress, known for her romance with a much younger (and more famous) boyfriend, confides that she's leaving the guy for someone more age appropriate. Meanwhile, Jake tries to upgrade his casual lover to a more serious relationship, and attempts to give imperious Naomi pointers on how to get along with the "little people" - the office staff.

Insomnia leads Jake to his hotel's lounge and a fateful meeting with a woman he thinks may be the girl of his dreams, a school teacher from the Midwest who's in town for a bachelorette party.

With Naomi momentarily incapacitated because of her advancing pregnancy, Jake is stuck juggling two warring teen divas who've been scheduled for meetings at the office at the same time, and surprise visits from Patrick and Adrian. Luckily he's got the help of the new office temp, Brooke.

Jake finds himself falling for Lisa, No. 47 on Ultima Magazine's super sexy 66 list, until he meets her friend, Josie, who just happens to be No. 3 and begins to wonder if the grass is really greener.

Shell-shocked when he learns that his ex-fiancée is getting married, Jake tries to flee the city by scheduling an exotic vacation, but an incoming storm leaves him stranded someplace equally foreign - the suburbs - with Adrian and his family. Meanwhile, when the clown he's hired for his kid's birthday bash doesn't show, Adrian gets Patrick to entertain.

Jake finds himself put to the test when Naomi goads him into throwing a fake "surprise" birthday party for her to help soften her dragon lady image. But things go from bad to worse when he accidentally admits to an influential gossip columnist just how difficult Naomi really is to work for - and she threatens to print it.

A boys' night out with Jake, Adrian and Patrick doesn't go as planned at the opening of a big sports bar owned by one of Jake's "biggest" clients - a New York Nick who is the shortest player in the NBA. Meanwhile, Jake is dumbfounded when he asks Brooke, the new temp, out on a date, and she says something he's never heard from a girl - no; and Naomi is desperate to do anything to ease the pain of her final weeks of pregnancy. .

Jake is trying really hard to make a good impression on Kylie as their date continues. Meanwhile Patrick is still stalking them, and Adrian gets into more trouble than he can handle when Shane drags him to a strip club.

Jake faces an unusual challenge when Brooke's ex-boyfriend, a schlubby Midwesterner, appears to reclaim his former girlfriend. Meanwhile, Patrick plans an outrageous stunt on Wall Street.

Jake and Brooke attempt a romantic evening in, but one interruption after the next stands in their way: Jake's client, the less-than-wholesome star of the kids' "Henry Porter" movie series, wreaks havoc in the hotel room next door; Adrian seeks reassurance from major guilt as he and wife Caitlin head off to the wedding of Jake's former fiancee; Patrick tries unsuccessfully to one-up David Blaine with a dangerous ice stunt, and Naomi goes into labor.