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[[Jennifer Connelly]] and Ione Skye vied for the role of Diane Court, but Skye was cast. [[Robert Downey Jr.]] was offered the role of Lloyd Dobler, but turned it down.<ref>{{cite web|url=https://www.howardstern.com/show/2016/05/04/robert-downey-jr-previously-howard-stern-show/ |title=Robert Downey Jr.…Previously on The Howard Stern Show |date=May 4, 2016 |website=[[The Howard Stern Show]]}}</ref> [[Christian Slater]] and [[Kirk Cameron]] were also considered for the role.<ref>{{cite web|url=https://www.indiewire.com/2012/04/5-things-you-might-not-know-about-say-anything-252505/ |title=Five Things You Might Not Know About 'Say Anything . .' |date=April 13, 2012 |last=Lyttelton |first=Oliver |website=[[IndieWire]] }}</ref> [[Dick Van Dyke]] and [[Richard Dreyfuss]] were considered for the role of Jim Court.<ref>{{cite web|url=https://www.vulture.com/2019/05/say-anything-cast-reunites-at-tribeca-film-festival.html|title=We've Been Mispronouncing Lloyd Dobler's Name from Say Anything This Whole Time|date=May 1, 2019|last=Reilly|first=Dan|website=[[Vulture (website)|Vulture]]}}</ref>
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