Just as they're heading back to colonial times, John Hancock and Sam Adams meet the woman of their dreams and decide that there's no better way to determine who gets to court her than a classic duel. In the meantime, in hopes of garnering good publicity for Chadwick's, Dan sets up a meeting with a local reporter, who winds up asking some challenging questions about Deborah's identity.
Having recently discovered time travel, Dan a facilities manager at a small Massachusetts college, has been transporting himself back to the 1700s to spend time with the colonial woman for whom he's fallen. In the present, Dan is misunderstood by all, and anxious that life is passing him by. But in the 18th century, he's absolutely hilarious - he gets the girl and makes friends.
But Dan's actions in the past are messing up the present. That woman he's dating is not just any woman. She's Paul Revere's daughter, Deborah, and Dan's meddling causes her father to delay his famous ride, which may have altered the outcome of the entire American Revolution. To set matters right, Dan enlists the help of Chris, a brilliant, polished and popular history professor at the college, who's now given the incredible opportunity to actually live the history he teaches.