Perfectly crispy tahini hamantaschen with a decadent and velvety chocolate filling. These bold and nutty flavored cookies are packed with sesame seeds and a little secret ingredient OLIVE OIL. 

A secret ingredient that nobody can put their finger on but gives these cookies an extra depth of nutty flavor. I promise they will wow everyone on Purim or any other day for that matter. 

I’ve you’ve been following me for a while, you know I have a borderline obsession with tahini. It’s like peanut butter, but better. 

Well, let me rephrase that. If peanut butter was a paper-pushing-government-official behind a desk, tahini would be a sexy Pierce Brosnan wearing a made-to-measure-tuxedo sipping a shaken, not stirred, martini.

Don’t get me wrong I love peanut butter, but I just so happens that I LOVE tahini. 

I was the preschooler having the tahini and honey sandwiches with the occasional sliced banana in perfectly toasted seeded bread, while all the other kids were eating peanut butter and jelly sandwiches for lunch. I love you, Mom. 

Fortunately, the "hummus craze" of recent years has made more and more people profess that same level of tahini love.  I guess the internet really is all about connecting. 

If you like tahini as much as I do be sure to check out my Tahini and Chocolate Chip Cookies. 

So adding tahini, chocolate, and sesame seeds to hamantaschen just seemed like the most natural way for me to go about making the triangular cookies. 

A couple of years I had no clue what hamantaschen even were. I’m of Sephardic origin and all I can say is that latkes, gefilte fish and like never made it to our table. Not that I cared to much because between you and me, gefilte fish an acquired taste that I just haven’t acquired. 

But cookies on the other hand? I'm always happy to take on new traditions that involve cookies. So for the past couple of years, I have been furiously baking hamantaschen of all flavors. All flavors except the traditional poppy or prune flavors, I must add. 

This year I decided to go for a more Mediterranean theme with my hamantaschen. If tahini and sesame seeds weren't Mediterranean enough, the olive oil ought to do it. 

Trust me using a good quality olive oil is a real game-changer. 

And since this hamantashen recipe is made with oil and the fact that there is no dairy in these at all means that they're absolutely kosher. 

Just in case you're wondering, no, the chocolate filling does not have any dairy. That velvety interior is made out of powdered sugar, tahini, cocoa powder, salt and the tiniest bit of oil and water. 

It's like Nutella but better, so much better. I think I might be making this spread over and over again and slathering all over warm toast. Breakfasts just got way tastier.

What are hamantaschen? 

Hamantaschen are very peculiar little cookies stuffed with some sort of delicious filling. You can recognize them by their very unique triangular shape. Although they can, and most definitely should, be eaten any time of the year, they are usually associated with the Jewish holiday of Purim, a Jewish holiday that commemorates how Queen Esther managed to save the Jews that lived in the Achaemenid Persian Empire from Haman’s evil plans to kill them all. 

The full story recounted in the Book of Esther which you can find both in the Tanakh as well as the Old Testament. I personally always urged my students to read the Bible. There is a reason why it has a best-seller through the ages. It has it all –intrigue, sex, deliverance, you name it. Even if you're not religious, it really is a great historical-ish read. 

The Book of Esther kicks off at the tail-end of a 6 month-long celebration that the Persian King Ahaseurus was throwing for all his subjects. During the party, the King got incredibly drunk and wanted his wife Vishti to parade in front of his drinking buddies wearing nothing but the crown jewels. 

Obviously, Vashti declined. Ahaseurus was fuming mad that his wife had dared challenge him in front of his courtiers and decided it was time to look for a more obedient wife. 

In retrospect, I’m not sure a Jewish woman is exactly an obedient woman, but hey, who I am to contest with the King of Persia. 

Finding himself newly single, Ahaseurus asked had his viziers to organize a little meet and greet for him with the most beautiful single ladies in his kingdom. Enter Esther into the picture, a beautiful Jewish orphan who had been raised by her uncle Mordechai. 

The King was so fascinated by her that they got married right away. Quite a jump for Esther from semi-destitute to Queen of Persia. 

As soon as Esther moved into the palace she started noticing an anti-Jewish faction in court led by non-other than viceroy Haman. Quick to navigate the palatial waters, the Queen conceals her religious identity.

Soon after, Esther’s uncle Mordechai finds out about a plot to assassinate the King, and dashes off to the palace. The conspirators are apprehended and hanged for treason. While at the palace gates, Mordechai runs into Haman but refuses to bow down to him as all others do on account of his faith. 

You see the viceroy already had a chip on his shoulder. He would have been a prince in his own right. He was a direct descendent of King Agag, ruler of the Amalekites, a people who were wiped out completely by Kings Saul and David. 

So when Mordechai refuses to bow down because he’s Jewish, Haman decided not only to eradicate Mordechai but all Jews from Persia. 

To do so he has very tall gallows built with Mordechai's name written all over it and starts plotting what day he will execute all the Jews by casting dice. 

Queen Esther finds out about the viceroy's plans, and with a little help from Mordechai's pleas, decides to thwart Haman's plans. She decides to throw two banquets, for her husband and his viceroy, a ruse to expose Haman in front of Ahaseurus. 

That night the King is having trouble sleeping, so he asks his scribe to read the court records to him. I guess this would be the Royal Persian equivalent of being a story to sleep. That's how Ahaseurus finds out that Mordechai has saved his life, and decided to reward Esther's uncle in front of everyone, further infuriating Haman. 

Over at dinner at Esther's quarters, the King finds out that Haman intends to kill his wife and her countrymen. He leaves the room enraged for a brief moment. When he comes back, Haman has fallen next to Esther in a desperate plea for mercy. Thinking Haman is coming on to the Queen Ahaseurus has him hanged in the same gallows that were built for Mordechai. There's poetic justice for you. 

This is the short version of the story, the long one involves much more intrigue and bloodshed, I told you it's a good read. 

But I suggest we focus on the good, the merrymaking but above all the cookies.