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Cautiously Pessimistic

A fun, insightful, and honest window into the dating scene of twenty-something-year-old Orthodox Jews.

Choni Hart is a 25-year-old Orthodox Jew ready to get married, however finding a wife has been harder than he ever expected. To cope with his disappointment (and also because it’s something fun to follow with his two younger sisters) Choni has been reading an anonymous blog about the trials and tribulations of Jewish dating, DearJane Does.

Tamar Adelson is Jane Does. Though she has no dating experience of her own, she has been running a dating blog advice column for the past year and a half.

When Choni and Tamar get set up Choni has no idea who Tamar really is, and Tamar has no idea how to tell him. As they grow closer both Choni and Tamar are forced to reconcile their expectations with the relationship they actually have.

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