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

When Jake decides its time to get serious about his love life, he sets his sights on Annie. To keep things safe, Annie invites Gordon to hang out with her and Jake -- and ends up making an interesting discovery in the process. Meanwhile, Bess is determined to prove that she and Steven are still a hotter couple than Nora and Elliot.

When Bess' boss, Vince, institutes ""bring your dog to work day"", Bess freaks out because she doesn't have a dog, so she asks Annie for one. Annie's dog at first seems too small, but Vince thinks it's perfect. Unfortunately, the dog is cast on Frasier and Bess has to take a new dog to work. He messes the entire office sniffing butts and other private parts. Bess gives up on the idea of bringing a dog to work, and just as she is ready to prove herself worthy to Vince she discovers that they've run out of business. Meanwhile, Nora reprehends Jake for dating one of her students. She dumps him and now Jake has Nora escort him home after dental surgery. Nora quickly sees in a sedated Jake a fun opportunity to tape everything he says and use it to make fun of him later. But what she didn't expect was Jake confessing that he feels lonely and wants to raise a family.