While rehearsing for the scene where Ryan Gosling lifted Emma Stone in the air "Dirty Dancing" style, Stone didn't realize she had a phobia of being lifted high up until the first time Gosling did it. She had a full meltdown, which Gosling described as "like a possum falling out of a tree and trying to scratch your eyes out." Afterwards she ran away crying and had to lie in bed watching Labyrinth to calm down. Her phobia came from when she was 7 years old and fell off the high bars in gymnastics and broke both her arms. They ended up using a body double for the lift, but they did use the recording of Stone's real screams.
Steve Carell has said that he hates the title of the film, stating that he couldn't imagine a group of college guys saying, "Five tickets to Crazy, Stupid, Love. please." One of the working titles Carell preferred was "The Wingman," which he felt was a boring title but more accurately described the film's plot.
The filmmakers offered a free iPad on-set to whoever came up with a title for the movie.
Emma Stone is a mere three days older than Lio Tipton. However, her character Hannah (approximately 24-25 years old) is seven to eight years older than Tipton's Jessica (17 years old).
The screenplay for this film was featured in the 2010 Blacklist, a list of the "most liked" unmade scripts of the year.