Frisch Teens Challenge Rabbi YY Jacobson | Q&A with Rabbi YY

Main Ideas

1. Reconnecting with Religion

A student asks how to handle losing love for religion. Rabbi YY Jacobson suggests that disengagement may stem from boredom, pain, or feeling that religion interferes with one’s life. Religion can feel negative, he argues, when it is presented only as rules, prohibitions, and punishment.

His advice is to seek a deeper, emotionally meaningful understanding of Jewish life through books, teachers, or mentors who explain what Judaism means and why its practices matter. He frames questioning as a possible sign of spiritual sensitivity and a search for depth, rather than simply a failure of faith.

2. Logic, God, Suffering, and Free Will

In response to a question about why God would create people who will do evil, Rabbi Jacobson distinguishes between what reason can explain and what it cannot. Logic is useful, he says, but it cannot fully grasp its own source—or the Creator—just as a created object cannot fully understand its maker. He uses examples such as a phone or tissue box to illustrate the limits of human understanding.

He presents the central religious claim as relational: God created people to choose a relationship with Him freely, rather than being programmed to do so. On suffering and evil, he acknowledges that explanations exist but says they cannot resolve every “why.” His response is that people should be humble about what they cannot know, trust that existence is rooted in divine love, and seek an open relationship with God.

3. What Judaism Is

Asked whether Judaism is a religion, ethnicity, or way of thinking, Rabbi Jacobson answers that it includes all three but cannot be reduced to any one of them. He describes Jewish identity as the “color” or energy of a Jewish soul, which he says remains even if a Jew is an atheist, leaves the community, or rejects Judaism.

He also explains “chosenness” as a responsibility: Jews are chosen to help teach that every person is chosen to discover and serve God in their own way. In his account, non-Jews do not need to become Jewish to fulfill their own spiritual role.

4. Recording the Rebbe’s Teachings

Rabbi Jacobson recounts growing up in Crown Heights and joining a group that memorized and transcribed the Lubavitcher Rebbe’s talks. He explains that Chabad’s founder, the Alter Rebbe, developed Hasidic teachings in a systematic, analytical style, and that this tradition continued through the generations.

Because recording devices could not be used on Shabbat and holidays, the hozerim (oral scribes) had to remember long talks—sometimes several hours—and write them down afterward. Rabbi Jacobson describes the work as exhausting but meaningful, and credits Rabbi Yoel Kahn with leading the effort. He says the resulting transcripts became hundreds of published talks and discourses.

5. Unanswered Prayers

Rabbi Jacobson rejects the idea that prayer is a vending machine: asking for a particular outcome does not guarantee that it will happen. He says every prayer has an effect, although people may not be able to see or measure it, including when someone is ill or dies.

He presents prayer’s deeper purpose as connection with God and openness to a perspective beyond one’s immediate wants. A “no,” he suggests, may redirect someone toward something they need more, though he recognizes that rejection and disappointment can be painful. He also emphasizes that God’s love is not disproved by hardship.

6. Being Genuine Without Saying Everything

On whether people should always show their true emotions, Rabbi Jacobson distinguishes honesty from total disclosure. His practical guidance is:

• Do not lie or put on a false persona just to please people.
• Do not assume every sincere thought needs to be shared. Consider whether the other person is ready to hear it and how close your relationship is.
• Choose words with kindness and tact. It is possible to avoid an unnecessary hurtful comment without being dishonest.
• Share deeper feelings with people you trust, rather than disclosing everything to everyone.
• Match the depth of your answer to the situation. A casual greeting does not require a full account of every personal crisis.

7. Evolution and Creation

Asked how evolution fits with the account of Adam’s creation, Rabbi Jacobson says Jewish thinkers hold different views. Some reject evolution, citing perceived gaps; others understand it as a process created or guided by God rather than as something wholly random. He does not present a single definitive resolution.

8. Personal Suffering and the Soul’s Wishes

A student challenges the idea that every disappointing outcome is simply “for the best,” giving the example of a parent unable to find work. Rabbi Jacobson acknowledges that such situations are difficult. He then offers his theological view that a person’s soul, as a part of God, may have a deeper understanding of what it needs than the person’s immediate desires do. He further claims that the soul has accepted the life and difficulties it encounters because they serve its purpose. He stresses that this belief does not mean pain is unreal or painless.

9. Intention in Prayer and the Role of a Minyan

Asked whether it is more important to pray with sincere intention (kavanah) or with a minyan, Rabbi Jacobson says intention and awareness are the essence of prayer, while a minyan is a valuable communal feature. He cautions that attending a minyan should not become a substitute for actually being present in prayer—and that choosing to pray alone should not become a convenient excuse.

He illustrates this with the contrast between a kosher but imperfect etrog and a beautiful fruit that is not the required ritual object: communal prayer is important, but it cannot replace the defining core of prayer, which he identifies as kavanah.

10. Learning to Recognize What to Ask For

Rabbi Jacobson suggests praying for the wisdom to recognize what one truly needs, rather than focusing only on immediate wants. He compares a passing desire to an itch: it may feel urgent, but it may not be what matters most.

He recommends reading Psalms (Tehillim), preferably with an English translation if needed. His suggested approach is:

• Read one or several chapters regularly, possibly following the traditional monthly division.
• Reflect on what David is expressing—his pain, anxiety, gratitude, and longing.
• Notice the recurring desire for devekut, or closeness and attachment to God.
• Use the Psalms as a model for prayer as an ongoing search for connection, not merely a list of requests.

11. Closing Message

Rabbi Jacobson encourages the students to live with purpose, authenticity, and awareness of the present moment. He describes the search for God as also a search for the divine energy within oneself. Books, synagogues, and schools can help people discover that connection, he says, but the ultimate experience is internal.

Speakers and Sources Featured

• Rabbi YY Jacobson — the primary speaker, answering the students’ questions and recounting his own experiences.
• Several unnamed student questioners — members of the teen audience whose questions cover religious disengagement, God and suffering, Jewish identity, prayer, authenticity, evolution, and prayer intention.
• The Yeshiva.net — identified in the closing sponsorship message as the source presenting the lesson.

Religious texts and figures referenced by Rabbi Jacobson: the Alter Rebbe and Tanya; Maimonides (the Rambam); David HaMelech and Tehillim (Psalms); the Lubavitcher Rebbe; and Rabbi Yoel Kahn.