Jake finds dating Naomi's sister uncomfortable when her ex-boyfriend, a performance artist, literally drops in on them.
Jake is asked to help a top client in publicly revealing he is straight, despite the fact he's part of a gay design team.
When an actress client dumps her young actor boyfriend for another man, Jake finds he has no choice but to get involved.
Jake tries to show up Peter by getting a famous actress to accompany him as his date to Peter's birthday party.
Jake meets an attractive school teacher in the hotel lounge when he is suffering from insomnia.
Jake and Naomi's temporary assistant must deal with warring divas when Naomi is sidelined by her pregnancy.
Jake starts dating a woman with a number 47 ranking on a magazine's sexy list, but then meets her friend, ranked number 3.
Jake finds himself stranded in the suburbs by a storm after he has books for an exotic vacation in an effort to get his mind off his ex-girlfriend's impending wedding.
Naomi asks Jake to throw a fake surprise birthday party in the hopes of softening her rough image.
One of Jake's clients invites Jake to the grand opening of his sports bar, so Jake invites Adrian and Patrick in the hopes of having a guys night out.
Jake tries to make a good impression on Kylie during their date, but finds it extremely difficult. Adrian gets in trouble during a trip with Shane to a strip club.
Brooke's ex-boyfriend comes back to try and win her affections.
Jake has a hard time working in a romantic evening with Brooke due to constant interruptions.