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Place a mixing bowl and the whisk attachment in the freezer for 5-10 minutes to chill. Pour 1 3/4 cup of the whipping cream into the bowl and beat until the mixture becomes bubbly. Slowly add 1 cup of the powdered sugar as you continue to beat. Beat on high speed until stiff peaks form. Set aside.
In another bowl, beat the cream cheese on medium-high speed until light and fluffy, 2-3 minutes. Scrape down the sides of the bowl, then add the peanut butter and the remaining 2 tablespoons of cream. Continue to beat until the mixture is smooth, scraping down the sides as needed. Slowly add the remaining 1 cup of powdered sugar and beat until well combined.
Gently fold the whipped cream into the peanut butter mixture. Divide the mixture in half.
Line a 9-inch baking dish with parchment paper. (You will want to make sure the side of your dish are at least 2 1/2 inches tall.) Dip both sides of a peanut butter cookie into the milk, then place in the bottom of the dish. Repeat until you have one layer of cookies on the bottom of the dish. You may need to break a cookie or two to make them fit the best. Spread half of the peanut butter mousse over the top of the cookies.
Peel and thinly slice the bananas. Place a single layer of bananas over the top of the mousse. Repeat the cookie layer, dipping the cookies in the milk first. Spread the remaining peanut butter mousse over the tops of the cookies, then add another layer of bananas.
In a mixing bowl, beat the remaining 2/3 cup cream until bubbles form, then slowly add the 1/2 cup powdered sugar. Continue to beat until you have stiff peaks. Spread the whipped cream over the top of the bananas in the dish.
Microwave the 1 tablespoon of peanut butter (I think this is easiest in a piping bag of ziplock bag). Drizzle the peanut butter over the top of the whipped cream.
Cover the dessert and refrigerate for 4 to 6 hours.