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Lana (Kristen Kreuk) and Lex (Michael Rosenbaum), Smallville
In an attempt to keep the show’s two main characters apart, Lex courted Lana, a high schooler six years his junior. Awkward! After seasons of using his extreme wealth to woo her, Lex eventually proposed to her in Season 6, with Lionel forcing her to walk down the aisle lest he kill Clark. Fortunately, Lex’s memories of their relationship were wiped out in the series finale. Thanks, Tess! Now can you do that to us too?