Jimmy's claim of demonic possession and Lily's skirt length prompt Sean's perceived battle with school head Sister Helen

Lily freaks out when Sean says they can't afford to send her on a ski trip with her classmates. But things get worse when she learns that Sean inherited some money and spent it on a guitar for himself.

Sean volunteers to referee Henry's soccer team and ends up making an unethical decision in the team's favor. Which in hindsight wasn't a great idea, when Henry gets an inflated ego. So Sean tries to make things right the following week by making an unethical decision in the opposing team's favor. . . Meanwhile, Lily flirts with the cute guy at the concession stand and the conversation leaves her walking on air. But when she starts to obsess over the introduction, she replays the scene over and over in her head, each time thinking that she made a bigger and bigger fool of herself.

During a stressful day at work, Claudia takes a puff of a co-worker's cigarette which quickly turns into an entire cigarette and then a daily habit. Desperate to keep her smoking habit from Sean and the kids, Claudia tries her best to smoke without being found out, but is busted by Lily. Lily makes a deal with her - she won't say anything if Claudia will get her a cell phone and Claudia agrees. Sean thinks that Claudia's bizarre behavior lately has something to do with him, prompting him to buy her the expensive armoire Claudia was admiring recently at the flea market. When her quest for a cigarette leads to her digging through the trash and landing outside Brad O'Keefe's window, she realizes she has hit a new low and swears off her habit. Meanwhile, after setting a date with Dean on her new cell phone, Lily is humiliated to find out Dean heard her gushing about him when the phone didn't turn off.