Beat sweetener, cream cheese, peanut butter in a large bowl until creamy. Set aside.
Whip heavy cream and vanilla extract together to stiff peaks in a separate bowl.
Fold whipped heavy cream into peanut butter mixture with a spatula. Some streaks are okay.
Add crushed cookies to the bottom of a jam jar.
Drizzle with sugar-free chocolate syrup.
Spoon peanut butter pie mixture on top.
Top with whipped cream, crushed cookies, sugar-free candies, and mini sugar-free chocolate chips as desired.
Refrigerate for 1 hour before serving.