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First, go to Curio Shop Lily and buy a wood stove for Dean when he's cold. Then ski jump until you've got two skis and can play head-to-head hard. Personal experience and multiple search sites say you must play head-to-head hard for about 12 to 18 times. Then, talk to Dean again, and he'll say something 97 percent of you will tune out, ending in a challenge for you to ski jump against HIM. Then, when you beat him, he's done. Completing Dean is the only way and second-to-last step to completing his best friend, Johnny.

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