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Nora is trying to quit smoking, but has a hard time doing so. Bess, Annie and Nora plan to go on a Macy Gray concert, but Bess has to cancel it suddenly when she has a work related problem. So Annie invites Jake to go in Bess's place. So Nora, Annie and Jake are driving back from the concert in Jake's car, when Nora, who is feeling totally left out of the conversation, asks Jake to stop by a 7-Eleven. While she is out, Annie tries to roll down the window but can't, and Jake helps her. As he leans on her, they sort of kiss. Annie is thrilled and makes a big deal of it, while Jake doesn't talk much about it. They set a date, but Annie gets stood up. Steven talks to Jake about it and Jake confesses that he did the best thing: end things before the sex, because he knows it would be weird since she's Steven's sister-in-law. After realizing that he likes Annie more than he'd like to, he goes over Steven and Bess's to apologize, only to find Annie going on a date with a guy she met at the bar