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No He didn't date Hermione Granger in Harry Potter. He thinks to highly of himself and would never date a muggle-born because he's a pureblood. Hermione also strongly dislikes Malfoy for being a bully and calling her a mudblood. (Hermione loves (and married) Ron in the books/movies.)

Also if you're a Dramione shipper you should check out Draco/Hermione fan fiction.

Emma Watson (Hermione) did however have crush on Tom felton (Draco), as she once say in a interview.

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