#8: Shidduchim (II): Now What? Dating, Doubts and Knowing It’s the Right One: With Dayan Posen

Once a shidduch is underway, the questions only become more complex: how long should it last, how do you navigate doubts, and how do you know when it’s right? In this episode, Dayan Posen addresses the realities of the dating stage, offering guidance on timing, clarity, and decision-making. From the role of parents and outside influence to recognising genuine compatibility, the discussion tackles the pressures and uncertainties that often arise along the way. Clear, practical, and grounded, this conversation helps bring direction and perspective to the most critical stage of the process.   Timestamps: - 0:00:00 — Intro; episode context and stage of shidduch (dating begins) - 0:01:21 — Torah/Gemara basis for seeing prospective spouse; purpose of dating - 0:04:35 — Awkwardness of dating; first/second date expectations - 0:08:01 — Dating coaches: pros/cons and when helpful - 0:13:00 — Misinterpretations on dates; examples (car stereo, phone-checking) - 0:16:07 — Discussing dates with others; confidentiality and who to consult - 0:20:37 — Parental pressure vs. giving space; response etiquette after dates - 0:25:23 — Etiquette: not saying no after one date; stages/types of dates - 0:30:55 — Different date styles (fun vs. serious) and what they reveal - 0:31:32 — Number of dates before decision; 4–6 vs. many more - 0:33:32 — Why people date more now; commitment/fear issues - 0:34:56 — Influence of friends’ opinions and peer pressure - 0:37:13 — “Not my type” / personal dealbreakers vs. societal expectations - 0:40:36 — Opposites vs. similarity in personality and compatibility - 0:42:11 — Pre-marriage independence differences (girls vs. yeshiva boys) - 0:45:34 — Impact of women’s careers/stimulation on marriage dynamics - 0:49:45 — Financial considerations, living in Eretz Yisrael, parental support - 0:52:46 — Expectation to live in Eretz Yisrael after marriage; alternatives - 0:55:47 — Discussing long-term location plans during shidduch - 0:59:17 — Anecdote re: commitments and financial changes - 1:01:15 — Compromising standards as one gets older; seek experienced advice - 1:02:18 — How to know if “the right one”: her geisha ha-leiv (heart’s feeling) - 1:06:39 — Managing anxiety before committing; leap of faith - 1:07:40 — Fear of missing a better match; practical grounding - 1:09:04 — Key qualities checklist: hashkafot, middot, smile; then chemistry - 1:11:36 — Debate on asking for photos before meeting; pros/cons - 1:14:43 — Parents seeing photos vs. children; risks of judging by pictures - 1:16:37 — Stigma of working boys vs. kollel; assessing commitment - 1:20:11 — Overall summary: challenges of the shidduch process; closing prayer