Jake is seeing two girls, Bethany and Michelle, and his friends see his fear of commitment is because he's still not over Annie. So he gets rid of everything that reminds him of Annie. Then Annie arrives at his door.
Patrick decides to open a bakery. Naomi discovers her maternal instincts. Jake reads the news that Konstantin Linardakis, a wealthy and handsome Greek shipping magnate, is marrying his friend Mark's ex-wife. Jake concludes that Mark "must be devastated" and since he himself is moping after Annie, decides to cheer them both up by taking Mark to a bar. He also invites Adrian. So far, so good - until Annie starts calling Jake, again and again.
Jake and Annie have to work together on a high profile project, which proves very difficult. Mark expresses his interest in Adrian's daughter's teacher, but doesn't call the teacher afterward, which makes her take it out on Adrian's daughter. And Adrian wants Mark to fix the mess, or else.
Annie denies that the kiss with Jake has meaning. Jake believes otherwise and decides to prove it, especially because he can't understand why Annie is marrying Danny. He tries to make her jealous by telling he's seeing Megan, the woman Annie introduced him to. Mark has discovered where the line judge who destroyed his career is hospitalized and intends to vent his anger on him. Naomi becomes the target of a young man's crush. Adrian's dental clerk is so red hot he can't help but let his eyes wander to her cleavage while he is treating patients - which leads to some ...
Having been distracted by Annie, Jake has failed to register that Patrick has fired him and hired a new publicist, Peter Beth, who is Jake's rival. Peter has challenged Jake to a 2-on-2 tennis match at a charity fund raiser, so Jake recruits Mark as his partner, because he wants to beat Peter and Mark is an ex-pro. But Peter has an ace in his sleeve. Meanwhile, Adrian gets to console Tanya the hot dental clerk. Also, Naomi is having difficulty telling the man she's seeing that she is a single mom.
One day to Annie's wedding. Mark urges Jake to stop the wedding Dustin-Hoffman-in-The-Graduate style. Jake decides to do it. Mark wants to come too, but Jake says no - until they discover that Jake needs Mark to drive stick. Adrian is already half on a date with Tanya in his mind and has trouble acting professional in her presence. Naomi, on the other hand, is trying to distance herself from Nugget. Patrick is nowhere to be seen.
To avoid awkwardness, Naomi fires Nugget and Adrian fires Tanya, but then Patrick hires her to eat cupcakes in his bakery's window. Meanwhile, Jake's client Laura suggests she and Jake mourn their break-ups together.
01/23 - Episode 2.08 - The Two Jakes: This episode will cover two sides of Jake: Friend-Jake and Lover-Jake. We will see how both react differently in various situations. We will also see a Friend-Lindsay and a Lover-Lindsay who will interact with both Jakes. Adrian's daughter Julia is in a play about the U.S. presidents; she plays President Grant. Lover-Jake and Lover-Lindsay attend the play. Friend-Lindsay will end up at the hospital, but fear not Friend-Jake is there to support her. This Friend/Lover-Jake thing will help Jake come to some conclusions about his love...