Slit each date down one side and pull out the pit, keeping the date in one piece. Line a plate with parchment.
Stir the tahini with the cinnamon and pinch of salt. Spoon about a teaspoon into each date and press it gently closed.
Melt the chocolate and coconut oil in a dry bowl set over a pan of barely simmering water, stirring until smooth.
Dip the top half of each date in the chocolate, let the excess drip, and set it on the parchment.
Sprinkle with pepitas and flaky salt while the chocolate is wet. Chill 10 minutes until set.