Pit the Medjool Dates and process in a food processor until all the dates are finely chopped, mostly blended, and sticky (small chunks remaining are ok). You may need to stop and scrape down the sides a few times in between.
Take out the date mixture into a microwave save bowl. If there are still large pieces of dates remaining, take a masher or fork and quickly mash them down.
Add the vanilla extract and 1/4 teasp non-dairy butter.
Microwave for 40-60 seconds, covered (depending on how powerful your microwave is, time may vary).
Remove, mix, and mash once more with masher or fork.
Coat your hands with a tiny amount of non-dairy butter or oil. Take the entire date-seed mixture into your hands. Roll it into a large sphere and then shape it into a 2-2.5" diameter cylinder by gently rolling it on a flat surface such as a cutting board.
Place it in an air-tight container (or cover completely) in the fridge for about 5 hours.
After at least 5 hours, remove the date-log from the fridge and slice it lengthwise with a sharp knife into ~1/4-1/3" thick cookie rounds. Place them back in the fridge in a single layer while you melt the chocolate. (see notes below)
Melt the Enjoy Life chocolate chips or bar pieces in the microwave in 20-30 sec. increments (mixing in between) or use a double broiler (I prefer a double broiler).
Once the chocolate is melted, take the date cookie rounds out of the fridge. I placed them on my cooling rack so that the chocolate drizzle could drop off, but you can just as easily use a tray lined with parchment paper.
Fill a ziplock bag or pipping bag with the melted chocolate. Cut a tiny corner off the ziplock bag if using. One by one, drizzle some melted chocolate on top of each date cookie.
Place the chocolate date cookies back in the fridge for a few minutes until the chocolate hardens.
Enjoy the chocolate date cookies immediately and store any leftovers in an air-tight container in the fridge for 1-2 weeks!
After placing the date-seed log in the fridge for 5 hours, the date cookies should slice easily and hold shape. If you find that the date-seed mixture is still sticky and does not hold shape well, then the dates used were either too soft or the mixture was not microwaved enough. They will still taste good, but will be softer and chewier than intended and may not hold the cookie shape.To melt the chocolate, I prefer using the double broiler method. Instead of using a pipping bag to drizzle the chocolate on top of each date cookie, you can use a spoon to drizzle or spread a thin layer of the melted chocolate on top.