The Hippie: Dreadlocks and Bagels
What: Mystical reflections of Yom Kippur
When: Saturday, September 22, 3:45 PM
Where: Quadrangle Club, 1155 E. 57th St
Why: Explore the oneness of time, space and consciousness with a totally far-out discussion by Rabbi Yossi Brackman on the mystical dimensions of Yom Kippur.

The Hipster: Way Too Cool for Hebrew School
What: Launch party for A Living Lens
When: Sunday, September 30 at 2 PM
Where: 618 S. Michigan
Why: Searching for your latest anachronistic style cue? Look no further than Alana Newhouse’s new book of photographs from the Forward’s 110-year-old archives, from Lower East Side pushcarts, a shtetl beauty contest, and labor rallies to unexpected gems such as Harry Truman's haberdashery, Rabbi Schachter-Shalomi explaining Kabbalah to the Dalai Lama, and a New Orleans synagogue flooded by Hurricane Katrina. Talk about vintage!

The Beshert Seeker: Something Old, Something Newish, Something Borrowed, Something Jewish
What: Speed dating
When: Tuesday, September 25th, 7:30 PM
Where: Bungalow Bar Lounge, 1622 W Belmont
Why: Are you dreading yet another Yom Kippur spent fielding the “So, are you dating anyone?” questions from the aunts and cousins? If you’re between the ages of 30 and 40, up your odds and improve your speed-talking skills with an evening of five-minute speed dates.

The Nouveau Jew: Better Late Than Never?
What: Free Yom Kippur services and break-fast
When: Friday, September 21, 6:45 PM; Saturday, September 22, 9 AM
Where: 2024 W. Webster
Why: Don’t be shy—these services are warm and user-friendly, with a heavy emphasis on English translation. Even if this is your first time in shul since your Bar Mitzvah, you’ll be able to follow along. The best part? Everything is free, including the break-fast.

The Super-Jew: You've Got the Spirit, Yes You Do!
What: Transformative Jewish renewal Yom Kippur
When: Saturday, September 21, Sundown
Where: Mitziut, 1545 W. Morse Avenue
Why: You're always renewing and reaffirming your relationship to Judaism, and Mitziut is all about Jewish Renewal. Their erev Yom Kippur services are led by Rabbi Menachem Cohen and Cantorial Soloist Layni Katz Myers, and are inclusive, participatory, and relaxed, with lots of music, sacred Hebrew chants, meaningful Torah teachings and ancient spirituality.

The Intellectual: Smarter Than Jew
What: Loop Synagogue high holiday music festival
When: Tuesday, Sept 18, 7:30 PM
Where: Chicago Loop Synagogue, 16 S. Clark St.
Why: You’re going to think deep thoughts in synagogue all weekend, so prep your brain with some stimulating Jewish music. The show features two acclaimed cantors and the Tel Aviv Lev-Ran Singers.

The Alterna-Parent: Day Care and Dinner Parties
What: Break-fast with Temple Sholom
When: Saturday, September 22, 6:30 PM
Where: Ann Sather's Restaurant, 3411 N. Broadway
Why: Too busy running after the little ones to organize a break-fast? Dart into super-parent territory by joining Rabbi Taron Tachman and Temple Sholom for Ann Sather’s Swedish pancakes with lingonberries, famous cinnamon rolls, and of course, the essential bagels and lox platter with all the trimmings. Bonus: Children 5 and under are free!