The 10 Worst Boyfriends Ever
Julie Gerstein / September 21, 2011
The Guy Who Sent Nude Pictures Of His Ex -- To Her Family
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While he and one recent girlfriend were dating, Dave Simmons (who is 51, and way too old to be pulling ridiculous schemes like this) took pictures of her engaged in sexual acts (with him) without her knowledge or consent. After the couple went through a nasty breakup, Simmons did what any jilted lover would: he had the sexy pics made into Christmas cards. And sent them to her entire family.