Using a stand mixer (or hand mixer + large bowl), whip togeter cream cheese, sugar, cocoa powder, and vanilla on medium speed until smooth, about 4-6 minutes.
Pause mixer and add Cool Whip to bowl. Use a spatula to thoroughly scrape the sides of the bowl, getting any excess sugar and cocoa and loosening the cream cheese from the sides.
Mix again on high until dip has a thick, creamy texture and is a rich chocolate color, about 2-3 minutes. Taste test dip; if the chocolate seems too sharp, whip in more powdered sugar (about 1/4 cup at a time) until desired sweetness is reached.
Serve chocolate fruit dip immediately with fruit or cookies of your choice.
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