I just watched Win a Date with Tad Hamilton (2004), and am bothered by the ending. Main character Rosalee dates celebrity Tad Hamilton while her best friend Pete pines away. At the end of the movie, she finally finds out that Pete is in love with her, and that she loves him back.
Sure, the underdog wins and that's usually great, but this best friend is creepy:
He tells Rosalee (in a misogynistic way) that Tad only wants to sleep with her, and that she's “asking for it”
He looks up movie times to check when Tad and Rosalee finish their date, then calls Rosalee's dad so see if she's home yet
He calls the police on Tad and Rosalee (illegally parked) so their make-out session is interrupted
As Rosalee's boss, he tries to make her work the late shift so she can't go out with Tad
Verdict: wtf.
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