S22E16: How To Navigate Uncertainty (In Dating) w/ Simone Stolzoff

Dateable: Your insider's look into modern dating and relationships

Yue Xu and Julie Krafchick

Sexuality, Social Sciences, Relationships, Science, Society & Culture, Health & Fitness

4.7 • 910 Ratings

🗓️ 26 May 2026

⏱️ 63 minutes

🔗️ Recording | iTunes | RSS

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Summary

If one things for certain, there's a lot of uncertainty in dating, relationships, and the world right now. We're joined by journalist and author Simone Stolzoff to talk about why people struggle so much with uncertainty and how this shows up in our romantic relationships. We're discussing the three traps that make us believe there's certainty even when there isn't, ways to build an uncertainty tolerance to apply to dating situations and relationships, and how to reframe 'not knowing' as something positive that sets us up for discovery to find the types of relationships and opportunities beyond what we thought was even possible. To learn more about Simone Stolzofff go to https://simonestolzoff.com. Get his new book 'How To Not Know: The Value of Uncertainty in a World that Demands Answers' wherever books are sold. ---- Take our Dating Archetypes quiz: https://howtobedateable.com/ Read our book: How To Be Dateable: The Essential Guide To Finding Your Person and Falling in Love: https://howtobedateable.com/ Try the Dateable AI Dating Coach: Get personalized advice trained on our years of podcast episodes, courses and frameworks: https://studio.com/dateable Follow us @dateablepodcast, @juliekrafchick and @nonplatonic. Check out our website for more content. Also listen to our other podcasts The Psychology of Relationships and Exit Interview available on Apple Podcasts, Spotify, or wherever you get your podcasts. WE WROTE A BOOK! HOW TO BE DATEABLE (Simon & Schuster) is available now: https://howtobedateable.com/ Want to remove distractions from your dates? Download Brick and get 10% off at https://www.getbrick.app/DATEABLE Our Sponsors: * Avocado Green Mattress: Check out their mattress and furniture sale: https://avocadogreenmattress.com/DATEABLE * Get Rain of Shadows and Endings wherever books are sold or at Kensington Publishing https://www.kensingtonbooks.com * Quince: Get free shipping and 365 day returns at https://quince.com/dateable * Ruggable: Get 10% off your first order, sitewide, with promo code DATEABLE at https://ruggable.com Advertising Inquiries: https://redcircle.com/brands Privacy & Opt-Out: https://redcircle.com/privacy

Transcript

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0:00.0	Hi, I'm U.E. Shue. And I'm Julie Kraftchick. We're active daters turned dating insiders. Here to dive into
0:06.8	everything, modern dating and relationships. Welcome to Datable.
0:15.4	Hello, friends. Welcome back to another episode of Datable.
0:21.1	Do you feel like you're in a period of uncertainty?
0:25.7	Who doesn't?
0:26.9	Who doesn't? There is so much uncertainty in my life, in the world, in the people around me.
0:34.8	There's just uncertainty is the norm. It feels like. And our guest today is
0:39.9	someone who studies uncertainty and how to navigate these uncertain times. His name is Simone
0:46.0	Stilsoff. Yes. And we wanted to talk to him. It was actually a serendipitous moment. I had an old
0:52.3	co-worker reach out to me to reconnect after decades.
0:56.6	And he was like, you know what? You should meet my friend. And he told me at first I was like,
1:01.5	uncertainty, dating. And I'm like, oh, uncertainty and dating. These really go together. He actually
1:07.5	could be a really great guest. And he shared that he has this new book that came out that's called How Not to Know. So he's leaning into being uncertain, but he's also the author of the good enough job. And he's really talked about just like how you could thrive in an uncertain world. And his work has been featured in the New York Times, The Atlantic,
1:29.1	Wall Street Journal, the Washington Post, and he even did a TED Talk. So really insightful
1:34.3	journalist who's been diving into this world and we loved applying this conversation to dating
1:40.0	and relationships. Yeah. And that's what we did here. We wanted to focus the conversation around
1:46.2	dating. And what are three traps that make us believe that there is certainty where none really
1:52.8	exists? Yeah, so it's liberating to realize like you're only fooling yourself if you think that you
1:58.7	can. And I think both of us were able to identify with some of these
2:01.8	traps and how they've played into our dating and relationships. And we really do go through
2:07.4	like a bunch of different scenarios at all stages of a relationship and dating. So it's really
2:13.2	fun to kind of go into that lens of looking at it like, okay, what do you do? These are the common
	...

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