P01BeginnerEnglish Only
Positive Word Power for Teens
The Language of Friendship and Happiness
Chana Nestlebaum / Chofetz Chaim Heritage Foundation
Best for: A brand-new pair that needs an easy, high-energy first book.
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One of the very few mussar (the Jewish tradition of working on your character) books written AT teenagers rather than adapted down for them. It asks the questions you actually have: is a joke ever off-limits, is criticism ever helpful, how do you tell someone you're angry without wrecking the friendship. Every chapter is built on a scenario from real teen life — the group chat, the lunch table, the team.
Why it works b’chavrusa: It literally ships with discussion questions, which makes it the closest thing here to a ready-made chavrusa (a study partner you learn out loud with) curriculum. Partners can each take a side of a scenario and role-play the better response.
How it breaks up: Short scenario-based lessons with discussion questions
Publisher: ArtScroll. View book
P02BeginnerEnglish Only
Praying With Fire Teens
Igniting the Power of Your Tefillah — A 5-Minute Lesson-A-Day
Rabbi Heshy Kleinman
Best for: A teen who shows up to minyan (the quorum of ten needed for communal prayer) but has never been given a reason to.
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Tackles the questions teens actually ask about davening (praying): why would Hashem (God) listen to me, why does it feel like talking to a wall, how do I get real face time with G-d. Each lesson takes five minutes, is illustrated with a story, and ends with a summary you'll actually remember.
Why it works b’chavrusa: A five-minute unit is the perfect warm-up or cool-down for a session, and the story-per-lesson means neither partner has to carry the conversation alone.
How it breaks up: 5-minute daily lessons, each with a story and a summary
Publisher: ArtScroll. View book
P03BeginnerEnglish Only
Living Emunah
Achieving a Life of Serenity Through Faith
Rabbi David Ashear
Best for: An anxious teen, or a pair whose schedule is unpredictable.
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Probably the most widely read emunah (belief and trust in God) book of the last decade. Built from Rabbi Ashear's Daily Emunah talks, it's a stream of short pieces — usually a story, then the point — about staying calm and trusting Hashem (God) when life doesn't go your way. Grades, rejection, illness, plans falling apart.
Why it works b’chavrusa: Every piece is two or three pages and completely self-contained, so you can open anywhere and never lose the thread if you miss a week. The stories are the hook; the discussion writes itself.
How it breaks up: Dozens of short self-contained readings
Publisher: ArtScroll. View book
P04BeginnerEnglish Only
The Six Constant Mitzvos
R' Yehuda Heimowitz & R' Shai Markowitz, from the shiurim of Rabbi Yitzchak Berkowitz
Best for: The Hashkafa (Jewish outlook — how to see the world) 101 slot — the single best structural starting point in the catalog.
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Six mitzvos (commandments) you're doing every second of your life whether you notice or not: believing in Hashem (God), not believing in anything else, His oneness, loving Him, fearing Him, and not chasing after your eyes and heart. Rabbi Berkowitz's approach makes them feel doable instead of overwhelming.
Why it works b’chavrusa: Six big ideas means six natural chunks. A pair can spend several weeks on each one and keep returning to 'how did this show up in your week?' Strong for teens with limited background because it starts at the foundations.
How it breaks up: 6 sections, one per mitzvah, each in short chapters
Publisher: ArtScroll. View book
P05BeginnerEnglish Only
Teens Talk
Because Teens Have Stories to Tell
Sarah Massry
Best for: Week one, when the teen isn't sure they want to be there yet.
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First-person accounts from real teenagers: a girl rebuilding her life after a spinal injury, a girl whose sister has an eating disorder, an introvert drowning in an extroverted family, plus bullying, social pressure, and some genuinely funny disasters. Not a mussar (the Jewish tradition of working on your character) sefer — a book of lived hashkafah (Jewish outlook — how to see the world).
Why it works b’chavrusa: Pure story format makes it the lowest-barrier text in the whole catalog. Ideal as an opening book for a pair still building trust, or as a change of pace alongside something heavier.
How it breaks up: ~20+ standalone first-person stories
Publisher: ArtScroll. View book
P06BeginnerEnglish Only
Self Confidence
Formulas, Stories, and Insights
Rabbi Zelig Pliskin
Best for: A short, easy read when you only have a few minutes a week.
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Rabbi Pliskin's core claim is that you already have confidence — you just haven't learned how to reach it. The book is built from short 'formulas' (one-line reframes you can memorize), stories, and insights on using words and mental imagery to get out of your own way. Cheap, short, and unusually direct.
Why it works b’chavrusa: The formulas are one or two sentences each, so a pair can read several per session, pick one, and both try it for a week. Very low reading load, very high conversation yield.
How it breaks up: Hundreds of short numbered formulas, stories and insights
Publisher: ArtScroll. View book
P07BeginnerEnglish Only
Wordwatch
A Shemiras Halashon Lesson-A-Day for Teens
Aliza Goldin & Sari Margolis
Best for: A girls' pairing that wants the Chofetz Chaim (Rabbi Yisrael Meir Kagan, 1838–1933) material in their own voice.
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A lesson-a-day shmiras halashon (the laws of careful speech — no gossip or harmful talk) book written specifically for teenagers, by two women writing in a teen voice rather than translating adult material downward. Each day is one short lesson tied to a situation you'd recognize from school or a group chat.
Why it works b’chavrusa: Daily-lesson format plus teen-specific scenarios makes it one of the easiest books here to run as a structured chavrusa (a study partner you learn out loud with), especially with girls in high school.
How it breaks up: Daily lessons
Publisher: Feldheim (Mekor). View book
P08BeginnerHebrew-English Facing Page
Pirkei Avosפרקי אבות
Ethics of the Fathers — with a Concise Commentary
Rabbi Meir Zlotowitz
Best for: Any pair, any level. The safest pick in the catalog.
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The compact classic: the Hebrew text of Avos (Ethics of the Fathers) with English translation and a short commentary underneath, plus an overview essay. Because each mishnah (a short passage from the Mishnah, Judaism's earliest law code) is one or two lines, you can spend a whole session on a single sentence and never feel like you're falling behind.
Why it works b’chavrusa: The gold standard for chavrusa — tiny units, facing Hebrew so a stronger partner reads the Hebrew aloud while the other follows the English, and at 64 pages a pair can genuinely finish it and make a siyum (the celebration held when you finish a book of Torah (the Five Books of Moses, and Jewish learning generally)).
How it breaks up: 6 chapters, ~100 individual mishnayos
Publisher: ArtScroll. View book
P09IntermediateEnglish Only
Living Kiddush Hashem
Sanctifying Hashem in Everything We Do
Rabbi Shraga Freedman
Best for: A JSU or public-school teen navigating a non-Jewish environment.
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About the fact that people are watching — and that how a Jew behaves in a store, on a plane, or at a job is itself a mitzvah (a commandment). Packed with true vignettes from Shanghai to Colorado, showing both gedolim (the great Torah leaders of a generation) and totally ordinary people pulling this off in unglamorous situations.
Why it works b’chavrusa: Vignette-driven, so a session is: read a story aloud, then ask 'where does this come up for you?' Especially resonant for teens in public school who are the only visible Jew in the room.
How it breaks up: Topical chapters built around true vignettes
Publisher: ArtScroll. View book
P10IntermediateEnglish Only
A Daily Dose of Bitachon
Filling Your Day with Trust and Reliance on Hashem
Rabbi David Sutton
Best for: A pair that wants accountability between sessions, not just reading.
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Bitachon (trust that God is taking care of you) as a daily workout — the author's own image is 'spiritual cardio.' Each reading reframes one anxious thought using classic sources on hashgachah pratis (God's personal involvement in your life) and the balance between hishtadlus (your own effort) and trust, then hands you a takeaway you can use that day.
Why it works b’chavrusa: More than 130 short readings, each ending in a practical takeaway. Clean, repeatable session structure, and the takeaways give partners something concrete to report back on.
How it breaks up: 130+ daily readings, each with a practical takeaway
Publisher: ArtScroll. View book
P11IntermediateEnglish Only
Open Your Eyes
Seeing Hashem Everywhere
Rabbi Dov Keilson
Best for: The science-minded teen who wants evidence, not exhortation.
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Based on Shaar HaBechinah of Chovos HaLevavos (Duties of the Heart, an 11th-century classic on inner life) and Rav (a rabbi) Avigdor Miller's approach: emunah (belief and trust in God) through actually looking at the world. It takes you on a tour of the human brain, ecosystems, and the cosmos and asks what all that engineering implies about the Engineer.
Why it works b’chavrusa: Each stop on the tour is a standalone unit that invites the pair to argue and add their own examples — much closer to a conversation than a lecture.
How it breaks up: Chapter-by-chapter tour of creation
Publisher: ArtScroll. View book
P12IntermediateHebrew-English
Lights Along the Way
Timeless Lessons for Today from Mesillas Yesharim
Rabbi Abraham J. Twerski, M.D.
Best for: A pair where the mentor is far ahead of the teen.
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Rabbi Twerski — a psychiatrist as well as a rav — takes Mesillas Yesharim apart and rebuilds it around modern problems: self-image, addiction, procrastination, the difference between guilt and growth. The accessible on-ramp to the Ramchal (Rabbi Moshe Chaim Luzzatto, an 18th-century Italian thinker).
Why it works b’chavrusa: Bridges the beginner/advanced gap. A mentor who has learned Mesillas Yesharim can pair this with the original, and a teen who hasn't still gets the whole structure in plain English.
How it breaks up: Follows the 26-chapter structure of Mesillas Yesharim
Publisher: ArtScroll. View book
P13IntermediateEnglish Only
Rabbi Yissocher Frand: In Print
Contemporary and Classic Issues Through the Prism of Torah
Rabbi Yissocher Frand with Yonoson Rosenblum
Best for: An older teen who likes to argue.
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Rabbi Frand is the most-listened-to Torah (the Five Books of Moses, and Jewish learning generally) lecturer in America, and this is a curated set of his talks put into writing. He takes a contemporary issue — money, honesty, ambition, how we treat people — and reads it through classical sources, usually landing somewhere you didn't expect.
Why it works b’chavrusa: Essay-length units mean one essay per session, and Rabbi Frand's style is argumentative in the best way: he raises the objection you were about to raise, which keeps two people talking.
How it breaks up: Standalone essays
Publisher: ArtScroll. View book
P14IntermediateEnglish Only
Masterplan
Judaism — Its Program, Meaning, Goals
Rabbi Aryeh Carmell
Best for: The 'why do we even do this?' teen.
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A systematic answer to 'what is Judaism actually trying to do?' — covering the purpose of mitzvos (commandments), the ethical logic behind kashrus (the kosher food laws) and Shabbos (the Jewish Sabbath, Friday night to Saturday night), and Jewish attitudes to money, animals, the environment, and society. Written by Rav (a rabbi) Dessler's own translator, so the thinking is first-rate.
Why it works b’chavrusa: Topic-based chapters work as standalone discussions. Ideal for a teen who is comfortable observing but has never been given the reasoning, and for mentors who want an argument to work through rather than a story.
How it breaks up: Topical chapters
Publisher: Feldheim. View book
P15IntermediateEnglish Only
Ethics from Sinaiפרקי אבות
A Wide-Ranging Commentary on Pirkei Avos
Irving M. Bunim
Best for: Pairing with the ArtScroll Pirkei Avos as the mentor's depth text.
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The great English commentary on Pirkei Avos (Ethics of the Fathers, a short book of rabbinic life advice), written by a layman for laymen. Bunim ranges across Torah (the Five Books of Moses, and Jewish learning generally) sources, world literature, and modern history to unpack each mishnah (a short passage from the Mishnah, Judaism's earliest law code), and he writes for someone living in a secular society rather than in a yeshiva (a school of advanced Torah study).
Why it works b’chavrusa: One mishnah per session with a rich, discursive commentary. Well suited to a Modern Orthodox or public-school teen because it constantly connects Avos to the world outside.
How it breaks up: Commentary on all 6 chapters, mishnah by mishnah
Publisher: Feldheim. View book
P16IntermediateHebrew-English Facing Page
The Ways of the Tzaddikimאורחות צדיקים
Orchos Tzaddikim — On Refining Character Traits and Maintaining Balance
Anonymous (15th c.), Trans. Rabbi Shraga Silverstein
Best for: A pair that wants to work on middos (character traits) systematically over a year.
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A medieval character-traits manual organized as 28 gates, each on one middah — pride, humility, anger, jealousy, joy, laziness, truth. Uniquely, it argues that no trait is simply good or bad; even anger and stubbornness have a right time and place. That makes it a surprisingly modern read.
Why it works b’chavrusa: One gate per session is a perfect unit, and the 'when is this trait actually good?' framing generates real debate rather than polite agreement.
How it breaks up: 28 'gates,' one per character trait
Publisher: Feldheim. View book
P17AdvancedHebrew-English Facing Page
Mesillas Yesharim — Jaffa Editionמסילת ישרים
The Path of the Upright
Rav Moshe Chaim Luzzatto (Ramchal), Elucidated
Best for: A serious yeshiva-track pair. The flagship Advanced pick.
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The foundational Jewish book on becoming a better person, laid out as a ladder: alertness, caution, zeal, cleanliness, all the way up. This edition uses the Schottenstein Talmud (ArtScroll's English Talmud) method — the Hebrew broken into phrases with the English woven in — so you learn the original text, not a paraphrase.
Why it works b’chavrusa: The phrase-by-phrase layout is designed for exactly this: one partner reads the Hebrew phrase, the other reads the elucidation (a running English explanation woven into the original text), and the Insights section becomes the discussion.
How it breaks up: 26 chapters, each with elucidated text plus Insights
Publisher: ArtScroll. View book
P18AdvancedHebrew-English Facing Page
Shaar HaBitachon — Jaffa Family Editionשער הבטחון
The Gate of Trust from Chovos HaLevavos
Rabbeinu Bachya Ibn Paquda, Elucidated
Best for: An advanced pair that wants one deep sefer (a Jewish religious book) rather than broad coverage.
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The single most famous treatment of bitachon (trust that God is taking care of you) in Jewish literature. It argues, systematically, that anxiety is a thinking error, and walks through exactly what you can and cannot rely on. The Jaffa elucidation (a running English explanation woven into the original text) makes a genuinely difficult 11th-century philosophical text readable.
Why it works b’chavrusa: Shorter than the other Jaffa volumes, tightly argued, and the Insights sections turn abstract logic into something to argue about. The pocket edition makes it portable for a mobile chavrusa (a study partner you learn out loud with).
How it breaks up: 7 chapters, elucidated phrase by phrase, plus Insights
Publisher: ArtScroll. View book
P19AdvancedHebrew-English Facing Page
The Way of Godדרך השם
Derech Hashem and Ma'amar haIkkarim
Ramchal, Trans. Rabbi Aryeh Kaplan
Best for: The teen who asks structural questions nobody in school can answer.
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The Ramchal's short, systematic map of everything: why the world exists, what a soul is, how prophecy and hashgachah work, what happens after. Aryeh Kaplan's translation is famously clear. Short but dense — closer to philosophy than to mussar (the Jewish tradition of working on your character).
Why it works b’chavrusa: Written in tight numbered sections, so a pair can take a half-page at a time and spend the whole session unpacking it. Best for teens who like systems and want the big picture rather than inspiration.
How it breaks up: 4 parts, subdivided into short numbered sections
Publisher: Feldheim. View book
P20AdvancedEnglish Only
Strive for Truth!מכתב מאליהו
Michtav Me'Eliyahu, Volume I, Parts 1–2
Rabbi Eliyahu Eliezer Dessler, Trans. Rabbi Aryeh Carmell
Best for: A gifted teen paired with a strong college mentor.
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Rav (a rabbi) Dessler's essays are the most intellectually ambitious mussar (the Jewish tradition of working on your character) of the 20th century — free will as a moving 'point of choice,' giving versus taking as the two operating systems of a human being, the nature of time and of miracles. Genuinely difficult, and genuinely worth it.
Why it works b’chavrusa: Discrete essays that stand alone, so a pair can pick the famous ones (Kuntres (an essay or short treatise) HaChessed, Kuntres HaBechirah) rather than reading front to back. Needs a mentor who can carry the harder passages.
How it breaks up: Standalone essays (kuntresim)
Publisher: Feldheim. View book