For the pudding, whisk together all ingredients in a bowl. Cover and transfer to the fridge to sit overnight and turn into pudding (give it a stir every so often if you think of it).
For the peanut butter topping, beat together the cream cheese, peanut butter, Swerve Confectioners, liquid stevia, and vanilla in a medium bowl. Fold in the whipped cream.
To serve, layer the pudding and peanut butter topping in individual glasses.
Store covered in the fridge for up to 5 days, and only add the toppings right before serving.