When Dan's ex-girlfriend Claire tells him that she is engaged, Dan reacts by telling her that he is running for Mayor against an unbeatable incumbent.

Dan believes that to have any credibility he needs to have a campaign office; Claire learns that politics is not as easy as working at a PR firm.

Claire holds her engagement party at the bar where Dan works, while Dan and Jeff try to line up some financing for the struggling campaign.

Dan and Jeff get their hands on the campaign platform of their main opponent, but are faced with a moral dilemma. Also Dan gets a new roommate.

Jeff has trouble convincing the other Mayoral candidates that Dan should take part in the upcoming televised debate; Dan and Brianna decide to go public with their romance.

As election day approaches, Dan and Claire struggle to express their feelings for each other while Dan's election fortunes take a turn for the worse thanks to a surprise rival.

Dan may be Mayor of Wessex, but rumour has it that he's been side-lined. To prove that he's in charge, Dan takes it upon himself to name the new ice rink after a local hockey legend, only to find out it has already been named after a Wessex philanthropist on her deathbed. And now that Claire is back for good, she decides to start her own PR company. It’s just too bad that Dan can't hire her to improve his own PR.

Dan wants the city of Wessex to go green with its garbage. He solves the garbage problem by striking a deal with the neighbouring city of Glenbridge, only to be foiled by their crafty mayor and her goat. The Mayor's new policy has everyone down in the dump.

Dan plans to open new bike lanes in Wessex, but first he will need a new bike, a point of contention with Claire. Mike wants Dan to share the bike lane with roller-bladers, but is there enough room? Over at Fern's, Fern has let their liquor license lapse, an oversight he doesn't share with Jeff.

Dan is mentoring a young "Mayor for the Day" and the kid is giving him a run for his money by undermining Dan's credibility with the media and City Council. Meanwhile, it's time for the annual Best of Wessex Awards, and Claire is so busy looking busy, she doesn't even realize she's in the running. Now that Jeff owns Fern's he thinks he has a stab at Best Bar Award, but Fern knows all too well - awards come at a price.

Dan is about to open the annual Porktoberfest by taking a bite of the Golden Bratwurst – a task made difficult by his vegetarian status. Jeff is confused by Dan's seemingly bi-dietary lifestyle. After a radio spot, Wessegonians start to question their own dietary choices, leaving a lot of uneaten pork in Wessex. Mike takes his role of Hambassador so seriously it has him donning lederhosen and eating more than his share of pork products.