In this episode, I chat with author and illustrator S.T. Schwartz about her book, "Cautiously Pessimistic", a delightful Jewish rom-com novel! We dive into the book, a story about a 25 year old boy named Choni who is ready to get married! Choni follows an anonymous blog about the trials and tribulations of Jewish Dating, Dear Jane Does. Then, he starts dating Tamar Adelson, who unbeknownst to him, is Dear Jane Does. The book follows their dating journey as they both are forced to reconcile their expectations of relationships with the relationships they actually have.
I ask S.T. about her process behind writing the book and the role of gender identity and compassion in the story. We also chat about whether the shidduch system favors men over women, some bad dating stories, how to be less antagonistic, and the importance of compassion. Happy listening!