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The Dating Optimist

Challenging tired dating myths one graph at a time—and giving you an edge in San Francisco’s weird and competitive dating market

Newsletter · By Paul the Optimist · Official site

Indexed issues, last 90 days
3
Latest publication
Sep 3, 2026
Audience
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Earliest in this view
Jul 10, 2026

Latest issues

  1. Issue · Sep 3, 2026

    Unexpected Lessons from My AI Honeypot on Hinge (opens the original)

    Excerpt · Neutral tone

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    Meet Chloe. She’s an attractive blonde woman in her early thirties. She lives in Pacific Heights, an affluent San Francisco neighborhood, and works for a biotech startup doing “Product Strategy”, whatever that means.She likes the outdoors, but she is not outdoorsy. Her adventure photos have the unmistakable look of a sunny afternoon somewhere on Amalfi Coast, complete with Athleta tights and Gucci sunglasses. Or a boat trip to Tahoe with her friends. Or a ski run in the Rockies; difficulty: medi

  2. Issue · Jul 24, 2026

    How to "Just Be Yourself": a Step-by-Step Guide (opens the original)

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    Every man who has struggled with some aspect of his romantic life has heard the same advice at least once: “Just be yourself.”It is usually offered with kindness. A friend sees your best qualities and assumes that, if you stopped overthinking and let them show, the right woman would appreciate you. Sometimes the advice comes with examples of men around you who seem to succeed effortlessly by being unapologetically themselves. The intended message is encouraging: you already have what you need.Ye

  3. Issue · Jul 10, 2026

    Do Manly Acts Make Other Men Look Handsome? (opens the original)

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    It’s no secret that San Francisco is not overflowing with traditional masculinity. “There are no hot men in San Francisco”, a comment on this TikTok reel laments. Comedians joke about it, female daters complain about it, and even some of the men seem resigned to the diagnosis.<a class="image-link image2" href="https://substackcdn.com/image/fetch/$s_!x9KD!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpu

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