The plot revolves around Gregory, aka the Wimpy Kid, looking for a date for the big Valentine's Day dance. Meantime, his dad's brother, Uncle Gary, moves in after losing all his money after buying a zillion shirts that are misspelled. Uncle Gary is full of dating advice...bad dating advice. After Gregory is turned down by every girl in school, he asks Abigail, after her date cancels, to join him on a group date with Rowley, his BFF. Gregory's mom is also freaking out because it's time for baby brother, Manny, to head to kindergarten! Alas, Manny prefers to play with his invisible friends and not flesh and blood kids. 

Will Uncle Gary ever move off Rodrick's favorite sofa? Will Manny make a real friend? What does the Valentine's Day dance hold for BFFs Gregory and Rowley?