Charlie has a slogan contest at Salinger's and the winner wants to bring homeless people to have dinner at the restaurant. Charlie has to kick them out so his clients won't leave and Grace prints in the paper what he did, giving him a hard time. They have a discussion and after Grace admits being wrong about him they come up with a solution. Sarah is worried because Bailey is drinking too much, but he says he's only celebrating. He tries to get in the hockey team but he's not in good shape, so he gets invited to the wrestling team, which is the worse in school. He doesn't support Sarah's new job and they have a fight. She says he's changed. Julia is having problems with the roofers. Alec offers her pot, and she turns it down. She talks with his brother and he fires him. They flirt. Claudia tries to get back at Charlie for not letting her go to the conservatory.

Bailey saves Callie from being raped. She is scared of going out of the house and Sarah tries to be her friend and wonders why she doesn't have many female friends. Charlie is helping Grace. He worries about her safety because she lives in a dangerous neighborhood. She tries to kiss him, but he tells her that he has someone - Kristen. After Sam gets fired for not covering the roof, Julia rehires him from her own money. He discovers her lie and she kisses him. Claudia is offered a column in the school paper about heart stuff and she soon realizes that something's up with Bailey. Callie tells him that she wants someone like him.

Joe is getting married, which reminds Charlie of his own wedding. If he and Kristen got married, they would be celebrating their first anniversary. Charlie asks Grace to the wedding, but she gets confused when he makes a speech that is definitely about Kristen. She tells him to make decisions about his life. Sarah wants to fix Callie with her cousin, but Callie turns it into a double date right away. She feels like Bailey and her are getting apart, and she decides to sleep with him, but Bailey can't do it. They promise to give it another try, but Bailey sleeps with Callie again. Sam doesn't want anything with Julia and Claudia says she's pathetic, but Julia insists and Sam decides to go back to the house.

Bailey is very excited with wrestling and wants to tryout for All Stars. Although Coach Petrocelli doesn't think he is able, Bailey gets obsessed to win. He wants someone to be there for him, but Callie is mad at him and wants him to move out, and everybody else is busy, but Claudia, who misses him at home. Bailey celebrates every victory with a few drinks, and every time he gets more and more drunk. Julia finds out that Sam was engaged and she joins him in his dinner with his ex-fiancée. She is getting married and he realizes he still loves her. Charlie gets an award for helping the homeless and realizes how much he likes Grace when another man asks her out.