Orthodox Conundrum
Orthodox Conundrum

The Dating Process: An Honest Conversation for Those Dating and Their Parents, with Rabbanit Shayna Goldberg (276)

January 12, 2026

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5 min read

The Dating Process: An Honest Conversation for Those Dating and Their Parents

Rabbanit Shayna Goldberg has spent 24 years teaching young women, first in American high schools and then at Migdal Oz in Israel, where she serves as a mashgicha ruchanit. She is not a therapist or a dating coach, but she has had countless conversations with students navigating relationships, commitment, and uncertainty. From that experience, she has developed a clear framework for thinking about dating and decision-making that avoids formulas or guarantees and instead focuses on helping people trust themselves.

The Foundation: Respect and Trust

Goldberg argues that the most important questions in dating are not about chemistry or checklists but about two core assessments: "Do I feel like I respect this person? And do I feel like I trust them?" These are not the same thing. Respect means looking up to someone, valuing how they carry themselves, how they make decisions, who they want to be. Trust means believing this person will be a good spouse, a good parent, a reliable partner even when they are angry or frustrated. In her experience, when relationships end, it almost always comes down to a failure in one of these two areas, not the absence of some specific quality on a list.

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What you'll learn

  • 1 (00:51) **The Two Core Questions: Respect and Trust** - Rabbanit Shayna Goldberg introduces the two foundational questions she believes are at the heart of every successful marriage decision: Do I respect this person? Do I trust this person?
  • 2 (05:44) **Shayna's Role: Not a Coach, But a Listener** - She explains that her decades of teaching and listening to young adults, not formal training, have given her deep insight into the dating process.
  • 3 (07:04) **The Building Metaphor: Slow and Steady Wins the Race** - Shayna uses the metaphor of constructing a building to explain why couples must build a solid foundation before racing to the top.
  • 4 (11:17) **The "List": Core Values vs. Perks** - Shayna discusses how to build the foundation, advising that a general sense of core values is more important than a rigid list of specific traits.
  • 5 (18:03) **When Chemistry Overrides the List: Self-Delusion or Growth?** - Scott asks how to tell if a powerful attraction is helping you grow or blinding you to your real needs.
  • 6 (20:10) **Figuring Out What You *Really* Want vs. What You're *Supposed* to Want** - She helps listeners distinguish between their authentic desires and the societal/familial pressure to want certain things.
  • 7 (24:35) **The "Am I in Love?" Question: High vs. Feeling Good** - Shayna addresses the common fear of not feeling a head-over-heels "high" even when everything seems right.

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Show Notes

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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).

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