Prep the Dates. You can buy pitted and already sliced dates or Slice each Medjool date lengthwise to create a pocket, but be careful not to cut them all the way through. Remove the pits and set the dates aside.
Mix the Filling. In a small mixing bowl, combine the peanut butter, vanilla protein powder, maple syrup, and vanilla extract. Stir until the mixture is smooth and thick. If it feels too stiff, add a tiny splash of water or almond milk (just a teaspoon at a time) to loosen it up.
Stuff the Dates. Using a small spoon, fill each date with about a teaspoon of the peanut butter mixture. Be generous with the filling so it peeks out of the date, giving that irresistible “stuffed” look.
Prep your melted Chocolate. Mix your chocolate and coconut oil and place into the microwave for 20 seconds keeping an eye on it so it doesn't overcook, you want it to be melted softly. Let it cool for a bit until it thickens a tad.
Grab a date and dip! Dip each date individually into the bowl of melted chocolate and make sure it gets covered, remove and place back into your cooling sheet pan. Continue until all are covered. You can use your fingers or a long toothpick to place and remove.
Garnish and Serve. Sprinkle a pinch of flaky sea salt on top of each stuffed date for that perfect sweet and salty combo. Arrange them on a serving plate or a neutral-toned wooden tray to elevate the presentation.
Store them in a glass container in the refrigerator and can be stored up to 5 days.