We open with Sydney and Andrew having lunch at Jodi’s 24-hour diner. Sydney tells Andrew that Simon is making her take a vacation to Hawaii. Sydney asks Andrew why he’s wearing a cardigan and then figures out that Andrew is dating Nancy again, an obsessive ex-girlfriend he swore he’d never get back together with. Sydney yells at him for getting involved with her again. Then, Simon and Zach appear. Simon hopes Sydney has a good time on her vacation though she doesn’t want to go.
At the office, Simon is pushing Sydney to leave when Lauren rushes up to them to tell Simon that the breakfast burrito people want to move the pitch to the next day even though it was scheduled for next week. Sydney thinks she should cancel her vacation but Simon says that he and the gang can handle it and pushes her into the elevator.
Simon, Zach, Andrew and Lauren are trying to come up with a pitch for the breakfast burrito people. Simon asks Lauren to read a poem of hers since “the best ideas come from life.” Her poem is depressing so then Sydney appears saying that she booked a flight for the following day to help them come up with an idea. Simon then asks if Andrew or Zach has a funny burrito story. Zach has one this girl, Natalie, he’s been seeing told him. After he tells the story, Simon, Andrew and Lauren can tell that Zach really likes the girl but Zach denies the fact that he has a crush. Then, Sydney reminds them all that they need an idea. Simon asks her if she trusts him. She says that she trusts him and will go on her vacation but asks to stay 20 minutes more because she has a thought that might help them come up with an idea. She then takes out the “creativity binder.” Simon, Zach and Andrew cringe at the sight of it. Then, Andrew gets a call from Nancy and Sydney tells everyone that Andrew is back with “Nancy Cardigan.” Zach and Lauren yell at him as Simon asks who “Nancy Cardigan” is. Sydney fills him in. Simon then asks Andrew if he likes wearing cardigans, after some coercing, Andrew admits that he doesn’t. Simon then suggests that Andrew creativity is being stifled by the cardigan and thinks they should burn it. Sydney, of course, is against it but Simon, Andrew, Zach and Lauren burn the cardigan in a trash basket. Sydney tries to put out the fire with some bottled water but there isn’t enough and the fire alarm triggers the sprinklers. Andrew picks up and carries her into another part of the office to try to keep her from getting wet but they both get soaked as does the “creativity binder.”
After the firemen leave, a soaking wet Sydney tells Simon that she wants to cancel her vacation but he insists she still go. Sydney and Andrew go in another room to find dry clothes. While they change, Sydney tells Andrew her sexual fantasy of being in Hawaii after a tsunami and giving a great pitch to a half-naked male Dole executive. Then, she tells him that he deserves better than “Nancy Cardigan” since he’s a funny, bright cute guy and that he shouldn’t be with someone who wants to change him. Then, Andrew kisses her. She pulls away and asks him why he kissed her. He replies that she sent out signs but she denies that she did. They both agree to forget it happened.
Sydney and Andrew rejoin Zach and Lauren. Sydney asks where Simon is and Lauren hands her a note that says Simon went out for a bite to find some inspiration. Sydney then says she knows where he went.
Sydney, Zach, Andrew and Lauren all go to Jodi’s Diner. Sydney tells them it’s where Simon worked before making it big in the advertising world and that he goes back to work there when he’s creatively stymied. The gang all but gives up on coming up with an idea and Sydney confesses that she and Andrew kissed and they both make light of it. Simon feels horrible that he ruined Sydney’s vacation that she didn’t want to go on and everyone else’s plans for the night but then says they can still have fun. Lauren reads another depressing poem to the crowd at the diner, Zach invites Natalie then tells Simon that he never wants to see her again after she won’t stop babbling. Then, Andrew gets a call from “Nancy Cardigan.” Simon goes over to Sydney, who tells him that she isn’t jealous. He replies, “You could have fooled me.” Then, he mentions that Andrew, Zach and Lauren all have lives outside of work and she shouldn’t be afraid to have one too. She says that it’s hard for her to let go sometimes. Simon says that she has to learn or she’ll end up like him and he wants more for her. She thanks him. She then says that she doesn’t know what happened with Andrew and suddenly says, “Am I a cheat?” Then, Simon suddenly kisses Sydney because he just came up with an idea.
The next morning, Simon presents his idea, “Cheat” on breakfast with a breakfast burrito. The gang loves it and are sure that the breakfast burrito people will love it too. The gang scatters and Andrew asks Sydney to call him as soon as she gets back from Hawaii. She says she will and grabs his butt since he’s still wearing green shorts that say, “Grab a can,” since his regular clothes were still wet. He tells her to warn him next time so he can clench.