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Rachel Dawes and Bruce Wayne

Christopher Nolan’s The Dark Knight was the pinnacle of the awkward romance between Gotham’s District Attorney and billionaire philanthropist Bruce Wayne. We weren’t huge fans of Katie Holmes in the role for 2005′s Batman Begins, but the casting of Maggie Gyllenhaal for Nolan’s sequel was downright weird. We’re huge fans of the actress, but the duo spent most of the movie looking like unwilling partners in a game of dodgeball. With their on-screen chemistry set to low, and Gyllenhaal acting like she’d rather be in Brooklyn knitting baby cardigans for her daughter, Ramona, we felt sorry for Dawes. She never really fits the bill as an empowered heroine and succumbs to a useless, by-the-numbers treatment as Wayne’s damsel in distress. How awkward was it for Bruce, too, when his childhood friend winds up wanting to marry his nemesis (Harvey Dent/Two-Face)? We love a good noir, but this romance failed with a flop.