Annie and Jake finally get engaged after six years, but her larger-than-life personality and his laid-back approach to life will severely test the theory of opposites attract. They quickly realize getting engaged was the easy part.

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.