The movie plays a small tribute to the late John Hughes. The high school David and Heidi attend is named J.W. Hughes High School (John Wilden Hughes), the first time we see Heidi David calls her Watts (Mary Stuart Mastersons name was Watts in Some Kind of Wonderful directed by John Hughes) and the story takes place in Illinois where John Hughes' stories take place.
Both Andrea Brooks (Paige) and Andrew W. Walker (Mr. Walsh) have both appeared separately on different episodes of Hallmarks Channels original series "When Calls the Heart" (2014).
TV Station in the Chicago Suburbs , (which Arlington Heights is ) always start with a W, not a K as was on the TV trucks outside of David's house.
Bailee Madison is wearing John Fluevog shoes with her prom dress