Chop chocolate in pieces, then melt in a microwave. Set aside to cool slightly.
Set aside 4 strawberries, then remove stems and slice the remaining berries.
Place strawberries in a small bowl and combine with 1 tsp. sugar. Mix well and set aside.
Chop Oreos into small pieces. Set aside.
Place cream cheese and 1/4 cup powdered sugar in a stand mixer bowl. Mix until smooth.
Add melted chocolate to cream cheese and mix until well incorporated.
Reduce mixer speed to low and slowly add 1 cup heavy cream.
Keep mixing until cream is fully incorporated, then increase speed and blend until mixture is light, creamy, and holds a soft peak. Set aside.
Whisk together remaining 1/3 cup heavy cream and 1 tbsp. powdered sugar in a small bowl until it can hold a soft peak. Set aside.
To assemble parfaits, place a spoonful of the cream cheese mixture in the bottom of each glass.
Top cream cheese with a spoonful of cookies, then a layer of strawberries.
Repeat these layers one more time, then add another layer of the cream cheese mixture.
Add a spoonful of whipped cream to each parfait, then garnish with the reserved strawberries.
Enjoy parfaits immediately or refrigerate until ready to serve.