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Cover the dates with hot water and let them sit for 5 minutes to soften.
Meanwhile, melt ¾ cup of the chocolate chips in a microwave-safe bowl in 30-second increments, stirring between each, until completely smooth.
Spoon about 1 teaspoon of melted chocolate into the bottom of each cup of a silicone muffin pan or silicone ice cube tray. Place in the freezer for about 5–10 minutes to firm up.
Drain the dates really well, then add them to a food processor with the peanut butter and maple syrup, if using. Process until fully blended and thick and paste-like.
If the date mixture is still warm from soaking, let it cool for a few minutes before assembling.
Take the chocolate cups out of the freezer and add a small spoonful of the date peanut butter filling to each one.
Melt the remaining ¾ cup chocolate chips and spoon over the top of each cup, covering the filling. Sprinkle with flaky sea salt, if desired.
Freeze for at least 1 hour, or until completely firm. Since the date mixture is warm after soaking, these need a little longer to set.
Once firm, pop them out of the molds and store in the fridge.