The Story Behind the Story | ST Schwartz presents ‘Cautiously Pessimistic’

Choni Hart is a 25-year-old Orthodox Jew ready to get married, however finding a wife has been harder than he ever expected. By now he’s become jaded and started approaching dates with cautious pessimism. To cope with his disappointment—and for something fun to follow with his two younger sisters—Choni has been reading an anonymous blog about the trials and tribulations of Jewish dating, Dear Jane Does.

Tamar Adelson is the author of Dear Jane Does. Though she has no dating experience of her own, she has been running a dating advice column for the past year and a half. She uses all of her own feelings and instincts to create her posts, but borrows stories from her friends and acquaintances to connect with her readers and strengthen her credibility.

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. “Cautiously Pessimistic” is a fun, insightful, amusing and honest window into the dating scene of twentysomething-year-old Orthodox Jews.

ST Schwartz is a twentysomething-year-old Orthodox Jew navigating the dating scene just like her characters! Similar to Tamar, she borrows lots of stories from her friends (usually with permission), but also uses some of her own. Professionally, ST works as a graphic designer with a special interest in typography and teaches at Yeshiva University. ST spent the past semester interning at Philomel books, an imprint of Penguin Random House, as part of the design team. She is excited and so grateful for the opportunity to share this story and add another rom-com to the world!