A young Irish woman loses her chance at a million dollar lottery when Gary swipes her dollar that she was going to buy the winning ticket with. To repay her he ends up caught up in a wild scheme that has them pretending to be engaged while Kate looks for a man she loves.
Gary travels back in time to 1929, and is the proprietor of a speakeasy at the location where McGinty's is currently located. He must try to prevent the St. Valentine's Day Massacre.
Gary finds out why he was chosen to receive the paper.
Gary must keep rescuing an accountant who is determined to become a bounty hunter.