During [Bert "the Conqueror" Kreischer's first visit](/show/segments/view/rachs-challenger-bert-conqueror/) with Rachael, he made the mistake of admitting the one crazy stunt he would never do - skydiving! That prompted Rachael to trade dares with Bert: If he jumps from an airplane with her, she'll do one of his challenges! Watch the video above to see if Bert makes good on his promise!
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