Place the Medjool dates in a heat-proof bowl.
Heat the milk in a small saucepan over medium heat until it starts to bubble, then immediately remove from the heat and pour it over the Medjool dates. Leave the dates to soak in the milk for at least 30 minutes and up to 1 hour.
Preheat oven to 350° Fahrenheit and line a 9x4-inch loaf pan with parchment paper.
Transfer the dates and milk to a blender or food processor and blend until completely smooth
Pour the date mixture into a mixing bowl, then add in the melted coconut oil and oat flour. Mix until everything is completely combined, then fold in the chocolate chips.
Transfer the batter to your prepared loaf pan and bake the cake for 20-25 minutes, or until a toothpick inserted down the center of the cake comes out mostly clean. Remove the cake from the oven and let it cool completely before slicing and serving.