“What I learned from going on 230 dates with EAs” by Ann Don Bosco

A conflict of interest to flag: I'm the founder of Settled, a relationship and matchmaking company with free and paid tiers. That may create bias in what I notice and what I recommend, so weigh these recommendations accordingly. I’d love for some of you to sign up to Settled, but my aim here is to share something useful whether or not you ever do.

What this post is and isn’t

• We’re writing this because we hope it provide helpful insights - people have also asked, so here it is!
• This post is based on:
  • Hundreds of hours of interviews and coaching with 350+ singles
  • Data from Settled: nearly 2K completed questionnaires & hundreds of feedback forms from dates we set up
  • An ongoing literature review (with help from Claude) - 70+ papers reviewed
• Our insights are observational, there's no control group and we collected all data for the purpose of setting up good dates, not research or analysis. We're including it because operational data from inside a matchmaking service is rare, not because it's complete or correct.

Some observations and learnings from building Settled

1. Dating apps are problematic; you should probably still use them

There [...]

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Outline:

(00:32) What this post is and isn't

(01:22) Some observations and learnings from building Settled

(01:27) 1. Dating apps are problematic; you should probably still use them

(04:11) 2. Just ask questions and be on time.

(05:21) 3. We're bad at knowing how the first date went.

(08:29) 4. Physical attraction is just one ingredient amongst many

(10:53) 5. Dating doesn't have to suck.

(12:38) If this resonates with you, join us

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First published:
October 5th, 2026

Source:
https://forum.effectivealtruism.org/posts/ecwyaawXhDjCmzHmb/what-i-learned-from-going-on-230-dates-with-eas-1

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Narrated by TYPE III AUDIO.

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