Hearing that Keanu Reeves and Winona Ryder may be dating is like winning the Fantasy Celebrity Hookups jackpot. Both of these lovable n’er-do-wells have been down on their luck recently, with a series of DOA movies, rumored engagements that didn’t pan out, and for Winona, the likes of Britney Spears and Lindsay Lohan stealing her stealing act. So whether or not the rumors are actually true, we’re throwing these two stars’ caution to the wind for them and giving them three good reasons why they most definitely should be, after the jump.