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The Most Awkward Photos Of Celebrities With Playboy Playmates

Whether they're Bunnies, Playmates or just models, celebrities loooove hanging out with the women of Playboy. They just choose to express it in different ways.

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Jeremy Shockey

Andrew H. Walker / Getty Images

Shockey feels the need to do something that will make it seem like he's casual about this situation, so he pretends to be a Bunny too.

Tinsley Mortimer and then-boyfriend Brian Mazza

Joe Kohen / Getty Images

Tinsley has her normal Tinsley face on, but Brian's trying so hard to be nonchalant about this encounter that he's focusing so. carefully.

Montel Williams and his wife

Joe Kohen / Getty Images

Montel suggested to his wife that they jam ourselves in the middle of this pack of Playboy models for a hot second and she readily agreed, with a pained smiled.

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