There are 8 discussion sessions in The Sinai Scholars course - each one addressing a different 'think Jewish' approach:

Session One 

A Question of Identity: Perspectives on Jewish Identity in the Modern World

You meet a Jewish person who says, “You know, I don’t know why people consider me Jewish. I do not support Israel; I do not ever visit a synagogue; and I do not celebrate any Jewish holidays.” How would you respond?
What does it mean to be a Jew? Is Judaism a religion, culture, nationality, or some combination thereof?
Since the dawn of time, individuals and groups sought to define and explain their identities, and Jews throughout the ages questioned the meaning of their Jewish identity. Today, the shifting sands of Jewish life require that this conversation persist but with newer insights and profounder definitions.

Session Two 
A People with a Purpose: Exploring Foundational Elements of the Jewish Ethos

If you were G‑d and you were going to address a once-for-all-time message to all of humanity, what would you say?
What messages does humankind need to hear today?
Mark Twain noted that while many nations filled the planet with sound and splendor, all of them soon faded and vanished. But the Jews are different, he noted. “All things are mortal,” he wrote, “but the Jew.” For Jews, survival is not celebrated for survival’s sake; survival is seen as a call to a purpose. A dialogue about the nature of this purpose is one crucial step in making this world a better place.

Session Three 
Reason and Ritual: On the Significance and Meaning of Jewish Observances

In medieval times, a despotic ruler once agreed to release a Jew from jail for one day each year to practice religion. The Jew was now in a quandary. Should that day be Yom Kippur? Passover? Rosh Hashanah? Some other day? How to choose?
What would you choose?
This leads into a broader discussion about Jewish rituals, which often seem foreign and archaic. In what ways can we find meaning and value in some of these observances?

Session Four 
An Oasis in Time: The Gift of Shabbat

Life is continuous and unrelenting. Might there be some benefit in a creative pause?
Enter the Jewish Sabbath. It is difficult to imagine a society functioning without a weekend, but this institution was unheard of in the ancient world. What meaning did Jews find in their Sabbath that allowed them to shrug off their cultural isolation?
Examining this question is relevant to those who are troubled that today’s society is insufficiently happy and inadequately connected in meaningful ways.

Session Five 
Love Matters: Discovering Jewish secrets of Love and Marriage

What is the secret to true and lasting love? How do I know if she/he is right for me?
Despite the rapid changes society has witnessed with regard to love, relationships, and marriage, the core ideal of finding someone with whom to live “happily ever after” is as strong as ever. Yet, an enduring and loving relationship is not easy to find and maintain.
Surprisingly, ancient Jewish wisdom can help our romantic and passionate love stand the test of time. Studying these insights can provide perspective in an age where many have been heartbroken by the withering of their idealized dreams of love.

Session Six 
Torah Ethics: Ancient System, Modern Applications

The Torah is ancient, so can it be of any consequence for today? Does the Torah have any insight to share about the novel realities of the modern world?
This lesson features fascinating scenarios plucked straight from the often bizarre and contradictory realties of our modern world, and scrutinizes them with the illuminating lens of the Talmud, the ancient book of Jewish wisdom.
The Talmud’s methodology, and its dogged pursuit of solving conflicting legal and moral claims, is staggering in skill and profundity. It dares to propel the intellect to a plateau it was unaware that it possessed. This lesson endeavors to tap into this timeless treasure. The lesson provides participants with newfound knowledge and skill to tap into Torah, which is the inheritance of all Jews, and to observe how it can be interpreted and applied to issue elegant and sound legal verdicts for the novel dilemmas of today.

Session Seven 
Inside Out: An Overview of Jewish Mysticism, Kabbalah, and Chasidism

Every visible structure has an inner power that energizes it. Jewish mysticism is one of the inner powers that sustains Judaism. As we will see in this lesson, this field of study contains many fascinating teaching that are relevant to our mission in life, our happiness, our relationships, and our self-esteem. On a societal level, the Jewish mysticism can offer ways for us to come together and interrelate politely and affably, even as people disagree and have important differences.
But for many generations, Jewish mysticism was not studied by most Jews. Why was this so? And what changed? More importantly, what makes a particular form of mysticism “Jewish”?
This lesson explores the history and development of Jewish mysticism, from ancient times until today. The development of Jewish mysticism is very much linked with twists and turns of Jewish history, and this session explores this link at great length.

Session Eight 
Forward Thinking: Examining Our Past to Forge Our Personal and Collective Future

In the 1980s, the historian Paul Johnson wrote that the world “might have been a much emptier place” without the Jews. But will historians say the same about the coming centuries of Jewish life?
This in turn raises a different question: Is it important that Judaism survive for centuries to come? And if the answer is yes, the question becomes what is the best way to ensure this survival? Suppose you are an authority on issues of Jewish continuity, and so Jewish leaders come to you to get advice about how to keep their kids engaged in perpetuating Jewish life. What will you tell them?
We can address these questions on a communal level, but it is also important that we address them on an individual level. This is why this lesson explores not only the trajectory of the Jewish collective but also how particular individuals—along with their personal backgrounds, unique talents, and individual proclivities—fit into the picture. As much as Judaism emphasizes the role of the collective, it highlights the role of the individual even more.