Chocolate Rolls

Chocolate Rolls made with challah dough, tahini, Silan (Date Syrup), Cocao and Cinnamon.

As I have written my first cookbook was Betty Crocker’s Century of Success Cookbook; The Best Gold Medal Recipes of 100 Years (1979). My Mom – and maybe yours – had the Betty Crocker Cookbook and I love all things Betty.

For years I instinctively turned to Betty Crocker to make sweet rolls for my family which while delicious includes substantial quantities of both butter and sugar that is not healthy really at any age, let alone your Second Middle Age.

Now we know better. We understand that reducing processed foods including added sugars is a great way to reduce inflammation and reduce the likelihood of what are called Non-Communicable Diseases (NCDs) of inflammation, which include high blood pressure, diabetes and certain cancers. That is a big part of the Microbiome Diet.

And even if your misspent youth – like mine – included quantities of sugar-intense processed foods it is never too late to make healthy habits. That is what your Second Middle Age is all about, learning from the past to feel good now and for the rest of your life.

I have been looking for ways to remake my sweet roll recipe for Second Middle Age without sacrificing taste and enjoyment. After all, it does not matter how healthy something is if no one wants to eat it.

In place of higher-fat, higher sugar sweet roll dough I have used my Traditional Challah recipe; I have swapped out sugar in favor of Silan (Date Palm Syrup), and exchanged Tahini for Butter/Margarine. I also increase heart-healthy, anti-inflammatory Cinnamon. The result are a beautiful Chocolate Rolls that taste great.

This recipe is a result of those efforts. These Chocolate Rolls that taste as good – or better – as traditional cinnamon rolls with healthier substitutions consistent with the Microbiome Diet.


1/2 of the dough from the Traditional Challah recipe

1 Cup Tahini (Whole Sesame Paste)

1/2 Cup Silan (Date Palm Syrup)

1/3 Cup Cocoa

1 T cinnamon


  1. Follow instructions for Traditional Challah.
  2. After the second rise, separate the challah dough into two sections, refrigerating the remaining dough.
  3. Stir together the Tahini, Silan, Cocoa and Cinnamon until smooth – if the mixture is too thick for spreading add water a Tablespoon at a time until you get it to a consistency which will be easy to spread on the dough.
  4. Roll out the challah dough into a rectangle, approximately 14 x 10 inches (or 35 x 25 cm), and spread the chocolate filling onto the challah dough, leaving a margin of approximately 1/2 inch (or 1.25 cm).
  5. Roll up the filled challah dough tightly, and seal each end.
  6. Move the rolled-up challah dough to a cutting board and with a sharp knife cut it into 1.5 inch (approximately 3.5 cm) slices.
  7. Place the slices into a greased casserole or other baking dish, allowing room for the chocolate rolls to double before baking.
  8. Spray the chocolate rolls with water and cover in a warm place for the final rise (proof) before baking – approximately 45 minutes to an hour should be sufficient, unless the room is very cold. If the room is very cold, you can put them in a warm – not hot – oven to proof.
  9. Once the rolls have doubled in size bake them at 350 degrees for 20 – 40 minutes. All ovens are different (and I have been cooking for the last 6 months in a toaster oven believe it or not). So it is good to check to see if you need to rotate the pan or otherwise adjust the rolls in the oven for even baking.


Published by skfinston

Born February 21, 1961 in Detroit, Michigan; enjoying 2nd Middle Age in Zichron Yaakov, Israel. After a misspent youth in the US Foreign Service (postings in London, Tel Aviv and Manila), I moved to the Semi-private Sector, working for a leading trade association in Washington DC before launching my own company Finston Consulting in 2005. Over the last 15+ years I have worked with innovative companies ranging from Fortune-100 to start up, as well as NGOs, and governments, including service as a cleared advisor (Secret level) to the Commerce Department and the U.S. Trade Representative (IPR, Tariff/Trade Facilitation). As a graduate of the University of Michigan, my degrees include a Bachelors of Science (Philosophy, High Honors), Juris Doctor and Masters of Public Policy. After law school I clerked at the US Court of Appeals for the Seventh Circuit before joining the U.S. Foreign Service (TSI-CodeWord Clearance). I am a member of the Illinois and US Supreme Court Bar.

3 thoughts on “Chocolate Rolls

  1. Betty Crocker reminds me of my mother also. Love this: That is what your Second Middle Age is all about, learning from the past to feel good now and for the rest of your life.

    Liked by 1 person

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