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Take 1/2 cup of boiling water - stir in dates that have been quartered and add 1/2 tsp. of baking soda. Let soak and your dates will be nice and soft. The soda makes the cells mushy and softens the dates.
I chop my dates, soak them in hot/boiling water, and then make a puree of just the dates and a small amount of milk (or whatever shake liquid you're using) before adding the other ingredients. Works for me!
Hi linzarella- I'm not sure where you are in the world, I'll assume in the US. There are different kind of dates, and here (in IL) we have a variety of soft and hard(er) fruit available, so I wasn't thinking about limitations. Aside from the suggestions already made, check if you have date paste where you are. Date paste is essentially dates for the lazy - pitted, mashed, and vacuum packed. But soft. That might work for you as well.
Date syrup is also available. After having date banana shakes in Israel, I've tried it both ways. The syrup definitely makes a smoother shake, which I prefer. Since some of my family has gone off dairy, I've also made it with almond milk and soy milk. Basically, with the date banana combination, you can't go wrong!