The Magicians (2000)

I am a man.  I have a fragile ego.  When people point this out, I get upset.  This, in addition to being a series of true statements, is the essence of the concept of male fragility.  Not all men have fragile egos, but enough do that it seems to be a pretty universal experience that women have to deal with.  This concept is explored (interestingly, by a male director) in The Sun Never Sets. 

The plot revolves around a few characters, but four are worth mentioning for this article.  Dakota Fanning plays the main protagonist, Wendy.  She is caught between three men: Jack(Jake Johnson), her most recent partner, Chuck(Cory Michael Smith), her (ex?) boyfriend, and to a much lesser extent Brad(Brandon Daley), who has a huge crush on her.  All three have central sins.  Jack’s sin is constantly changing his mind and sending mixed signals in a way that could be avoided if he just calmed down and thought through his emotions.  Chuck’s sin is not being open and honest with his partner and hiding things like his bad credit score, as well as some alluded-to bad behavior that lead to the first breakup.  Brad’s sin is, well, he’s he’s kind of like Bear from Obsession if he never got his hands on the one-wish willow.  Another movie, directed by a man, that deals with men not handling their own emotions and, as a result, hurting women.