As we start off the second season, Jake is on the trail of a group of bold daytime kidnappers; Leslie and Jake take steps to move on from each other as Rose tries to figure out the next steps after Mal’s heart attack. Mal is told by Rose in no uncertain terms that he has to take it much easier. Jake plays prisoner when he goes “inside” to find out the location of some stolen diamonds from a gang of incarcerated criminals; Mal finds out that Rose has been keeping a big secret from him; Tinny’s money-making scheme starts to take root. Gordon Pinsent, Alan Doyle & Mayko Nguyen guest star in this one. The Doyles are employed to help a comedian (Don McKellar) on the edge of a comeback find a dangerous stalker; Leslie defines the boundaries for the men in her life, including Jake; Allison reveals something to Jake that could be a game-changer.
It gets personal when the Doyles band together to protect someone they love from the cops and from a killer; Tinny gets in a little further with her new hobby and her new friends. She pulls in Des as her way to get some things done and the poor dude has such a big crush on her that he will stumble into anything for her. It’s matrimony – Doyle style – as Jake and Mal are tasked with finding the person responsible for sabotaging an upcoming wedding; Mal and Rose fix a bump in the road in their relationship as Jake and Allison hit a stride in theirs; Des comes to Tinny’s rescue but ends up exploding her plans in the process. When an old Doyle family friend accidentally goes missing at sea, the Doyles are hired by his daughter to find out what really happened. Turns out he fakes his own death. Oh and Jake is forced to bail out Christian and picks up another line of business and a pile of new debt.
Jake and Mal are called to check into some death threats that have been made to a respected psychiatrist; an old “friend” from the past shows up and makes an interesting proposition to the Doyles; after Leslie’s close call, Jake and Leslie find themselves struggling a little in their new romantic relationships. The Doyles reluctantly take on a case from dodgy Martin Poole (Nicholas Campbell) when he promises them a big payday; Jake and Allison encounter friction when their professional lives impose on their personal relationship; Jake gets an interesting job offer from an unlikely source. When Des finds himself in a very bizarre and compromising position, the Doyle clan works overtime to get him off the hook; Jake meets someone who has been complicating Allison’s life; Tinny and Des start coming to terms with their feelings for each other. Crime novelist Garrison Steele (Victor Garber) returns again to both hire and torment Jake to help him research a murder case; Jake and Leslie struggle to keep their mutual affection for each other in check; Allison receives some much-needed help from Jake.
Jake buys an expensive gift for Allison only to have it stolen by a thief; The Mayor finds himself in a compromising position and asks for Jake’s help and his silence; Mal has trouble telling a lie to his kids; Leslie thinks she’s being followed. The Doyles are hired by a real estate agent to investigate a series of strange occurrences at the site of her controversial housing development; Leslie uncovers some suspicious facts about the Mayor; the tension between Jake and the Mayor hits a high point; Allison makes Jake a serious proposition. When Tinny and Des are snatched from the safety of the Doyle home in broad daylight, Jake is forced to confront a dangerous man from his past (Paul Gross) to get them back; Leslie loses something else very precious to her; Jake makes a decision about his future with Allison.