Line a baking sheet with parchment paper. If the dates are not pitted, carefully use a paring knife to slit each date lengthwise without cutting completely through. Remove and discard the pits.

Stir the tahini to fully incorporate the oil and solids. Add approximately 1/2 teaspoon of tahini to the center of each date, then gently press the sides closed. Arrange the filled dates on the prepared baking sheet and freeze until the tahini is firm, about 20 minutes.

Place 6 ounces of chopped chocolate, or 1 cup of chocolate chips, in a microwave-safe bowl. Heat in 30-second intervals, stirring between each interval, until the chocolate is fully melted and smooth. Alternatively, melt the chocolate using a double boiler by setting the bowl over gently simmering water and stirring until smooth.

Remove the dates from the freezer. Using small tongs or a fork, dip each date into the melted chocolate, ensuring that the tahini filling is completely covered. Allow excess chocolate to drip off before placing the coated dates back onto the baking sheet, leaving space between them to prevent sticking. If additional chocolate is needed, melt the remaining 3 ounces (or 1/2 cup) and continue dipping.

If desired, sprinkle flaky salt over the dates while the chocolate coating is still wet. Refrigerate the dates for approximately 30 minutes, or freeze for at least 15 minutes, until the chocolate is completely set.

Serve the dates chilled. Store in the refrigerator for up to 1 week, or freeze on the baking sheet until solid before transferring to an airtight, freezer-safe container for up to 3 months.