Tom Green

After dating Tom Green, it's safe to say that Drew definitely doesn't stick to one type of guy. While filming Charlie's Angels together, the angel and comedian took their romance off screen. The relationship definitely had some ups and downs -- Drew stood by Tom as he dealt with cancer, and later Tom proposed to her in Cabo San Lucas with a Tiffany engagement ring. The lovebirds exchanged vows in front of 100 guests in a private Malibu estate, but their marriage only lasted five months.

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