Intro

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/ - and paid subscribers get this and other episodes of the Orthodox Conundrum Podcast ad-free and with early access and additional bonus content!

One of the most common questions people ask about dating is a deceptively simple one:

How do I know?

How do I know whether to keep dating this person? How do I know whether this is the person I should marry? How do I know whether my doubts mean something is wrong, or whether I'm just afraid?

For many people, dating becomes emotionally exhausting not because they lack options or insight, but because they believe that there must be a single, correct answer… and that getting that wrong would be catastrophic. That pressure often leads people to rush, to freeze, or to outsource responsibility to parents, rabbis, friends, or even strangers.

My guest today, Rabbanit Shayna Goldberg, offers a very different (and deeply liberating) way of thinking about dating and decision making.

Shayna is not a dating coach and not a therapist. She is a veteran educator who has spent decades teaching and listening to young adults as they navigate relationships, commitment, and uncertainty; she is also the author of What Do You Really Want? Trust and Fear in Decision Making at Life's Crossroads and in Everyday Living. What she brings to this conversation is not formulas or guarantees, but clarity.

We talk about why the hardest decisions in life are rarely between right and wrong, but between multiple possibilities. We explore how fear quietly shapes many dating choices, whether it's fear of being alone, fear of hurting someone, or fear of committing. And we focus on two core questions that matter far more than any checklist:

Do I respect this person?

And do I trust this person?

We also discuss how much weight to give chemistry, how to think about religious differences, when outside guidance helps and when it harms, and how parents can support their children without controlling their choices.

If you've ever felt stuck, pressured, or overwhelmed in dating, or if you're a parent trying to help without violating boundaries, this conversation offers wisdom, perspective, and, I believe, a welcome sense of calm.

Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108).

Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse.

Write to aliza@jewishcoffeehouse.com to learn all about creating your own podcast.

Music: "Happy Rock" by bensound.com