Place the bowl of the ice cream maker in the freezer the night before.
Blend all the ice cream ingredients, except unsweetened chocolate chips and vanilla in a blender until well combined or blend in a medium saucepan with an immersion blender.
Pour into a medium saucepan and bring to a boil over medium heat stirring frequently. Do not let this mixture burn! Once it comes to a boil, continue to stir for a few minutes until thick. Remove from heat, add chocolate chips and vanilla, and stir until chocolate is melted. Blend mixture with an immersion blender for 1 minute (or transfer to a blender and blend). You can leave it in the saucepan, transfer it to a bowl or (my preference) transfer it to a large measuring cup with a spout. Cover and place in the refrigerator until completely cool (at least 4 hours).
Meanwhile, prepare the cookie dough: blend dates, almond butter, sugar, and water in a blender until smooth.
Transfer the date mixture into a medium-large bowl and stir in the almond flour, salt, baking soda, and chocolate chips until well combined. The mixture will be slightly sticky.
Line an 8 ½ x 4 ½ or 9 x 5- inch loaf pan or an 11 x 7 baking dish with unbleached parchment paper, leaving a 1-inch overhang along the sides. Press half of the cookie dough mixture at the bottom of the pan, creating an even layer. You can fold in the excess parchment to press against the dough to avoid sticking. Place a second sheet of parchment over the first cookie dough layer and press the remaining cookie dough mixture into an even layer. Place loaf pan with both cookie layers in the freezer. (Alternatively, press the entire mixture into a parchment-lined pan and freeze. Cut in half horizontally before filling with ice cream.)
Once the ice cream mixture is cool, churn in the ice cream maker according to the manufacturer’s instructions.
Remove loaf pan from freezer and remove the top cookie dough layer. Spread about 2 cups of ice cream evenly over the first cookie dough layer inside the loaf pan. Gently press the second cookie dough layer over the ice cream to create a sandwich. Place in the freezer until the ice cream firms up a bit so it’s easy to slice. I usually make this the day before I want to serve it, but holds up well after a week or two as long as it’s well wrapped.