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.

What was going to be a straight-forward race for Mayor gets complicated when more candidates come forward, but luckily Dan's good friend Jeff is there to help him run his campaign.

Dan's stand on cats becomes a hot button campaign issue, but he finds two unlikely allies, his ex, Claire, and Brianna, the niece of his main opponent.

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.

While out campaigning Dan and Jeff are threatened by a mascot; Claire re-dedicates herself to her relationship with her fiancé.

Dan struggles to find the perfect symbol for his campaign for Mayor, while trying to date Brianna. Claire obsesses about trivial wedding details.

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.

While taking part in the candidate's debate, Dan gets embroiled in a career-ending muffin issue. Jeff is in trouble at his own work.

Dan gets some unexpected help in the campaign that gets both he and Jeff into hot water; Claire deals with the fall-out from her decision about the wedding.

With days to go before the election and hardly a Dan for Mayor lawn sign in sight, Dan gets some help on the campaign trail. Jeff gives Claire career advice.

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 gets on the wrong side of the Chief of Police when he tries to stop the upcoming purchase of 50 Speedoos (personal mobility devices). Although the Chief appears to accept Dan's decision, bad luck suddenly falls upon Dan and his friends. Mike's moustache finally comes in handy when he bonds with the boys in blue.

Dan jeopardizes his popularity when he proposes a property tax hike. A council meeting has him running late for his stint as a celebrity judge at a spelling bee. His tardiness doesn't go unnoticed and Dan forgets to go "off the record" with an overzealous, student journalist, resulting in a larger story in the Wessex Herald highlighting Dan's extraordinary spelling skills. Meanwhile, Mike finds himself upgrading on the girlfriend front.

Dan hosts his first annual Mayors' Conference only to learn that hanging out with the mayors isn't much different than being back in high school. Now that Claire and Dan are a committed couple, she needs to move all her stuff out of storage and since Dan is too busy with the conference, Claire turns to Jeff and Mike for help. Suddenly a competition develops when they each work hard to ensure that the other isn't available.

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 wants Wessex to be featured on the upcoming Art Trail, but Wessex doesn't have much in the way of art. Dan remedies this by commissioning a sculpture. Fern's gets a VLT (video lottery terminal) machine, which turns out to be quite addictive. Claire is bidding for a new job – it just happens to be an anti-gambling campaign.

Everyone wants a piece of the Mayor. Dan feels obligated to take on a speaking engagement for Fern but doesn't clear it first with his Chief of Staff, landing him on stage at a pot rally. Claire's parents are divorcing and Mike is devastated. When he tries to intervene, he ends up in a completely inappropriate and unintended dating situation.

As the new Mayor of Wessex, Dan finds himself having to attend a variety of events from pig roasts to pancake breakfasts. With Claire on his arm, he is unsure whether she is a political asset or liability. Alan already has his mind made up and imposes himself as the Mayor's handler by keeping Claire occupied. Mike tries to insinuate himself into a budding friendship with Jeff by pointing out that Mayor Dan doesn’t have much time for his old pal Jeff anymore.

Dan takes a trip down memory lane when he visits his high school workplace, Old Fort Wessex. Sadly, the fort has seen better days, so Dan commits to his old boss, the Fort's General, that he will do his best to turn things around. Claire plans to lure Japanese businessmen to Wessex and inadvertently creates a solution for the cash-strapped Fort. Meanwhile Jeff tells Fern that there are tunnels under the bar, and all the routes lead to Old Fort Wessex.

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.

The Mayor's relationship with Claire has him providing full disclosure to the questionably ethical Ethics Commissioner. Jeff attempts to out-customer service Fern and winds up behind bars. His one call goes directly to City Hall hoping his buddy the Mayor can make things right.