TThe Diary of a CEO
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Mindset

Friendship Dating

Find adult friends through repeated activity dates and gradual value tests

Difficulty
Moderate
Time to result
~months to results
Steps
5
Confidence
96%

Van Edwards recommends approaching adult friendship with some of the deliberateness used in dating. Begin in a recurring activity you genuinely enjoy—running, football, hiking, pickleball, or another shared interest—because repeated contact creates low-pressure openings. When someone seems promising, invite them on a friendship date and vary later settings so both people can observe compatibility beyond one context. Look for shared values, similar positive associations, and the ability to enjoy the same kinds of experiences. Deepen slowly rather than moving immediately into intense disclosure or dependence. Van Edwards illustrates the idea with her own search for close women friends in Austin, though her restaurant “test” is a personal example rather than a requirement of the method.

Origin

Extracted from The Diary of a CEO

Core principles

  • 01Finding a close friend deserves deliberate effort
  • 02Shared activities create repeated opportunities for connection
  • 03Compatibility should be tested gradually
  • 04A small number of strong friendships can be enough
  • 05Different settings reveal different parts of a person

How to run it

  1. 1

    Choose your activity pool

    Pick a recurring activity or place you truly enjoy and where compatible people are likely to return.

    Pro tip Repetition matters more than attending one large event.

    Watch out Do not choose an activity solely because it seems socially strategic.

  2. 2

    Build micro contact

    Say hello, ask a specific low-pressure question, and let familiarity accumulate across meetings.

    Pro tip Use the shared activity as the first conversation anchor.

  3. 3

    Invite a friendship date

    Ask a promising person to join a simple activity or place you would both plausibly enjoy.

    Pro tip Keep the first invitation bounded and easy to decline.

    Watch out Do not treat a polite decline as a complete judgment of the person.

  4. 4

    Vary the context

    Meet in more than one setting and notice how the relationship feels across different activities and levels of structure.

    Pro tip Choose settings that reveal a value important to you without creating a trap.

    Watch out Do not deliberately humiliate or stress-test the person.

  5. 5

    Deepen gradually

    Increase time, trust, and personal disclosure as mutual interest and compatibility become clearer.

    Pro tip Aim for a few excellent relationships rather than a large indiscriminate circle.

    Watch out Avoid moving into dependency faster than the evidence of trust supports.

In the wild

A recurring hiking group

A newcomer attends the same weekend hiking group for several weeks, exchanging brief comments with familiar faces. After discovering a shared interest with one participant, they suggest a short separate walk. Later meetings vary between hiking and coffee, allowing the friendship to deepen without an immediate high-stakes commitment.

Repeated shared activity turns a weak tie into a tested friendship.

Common mistakes

Expecting instant closeness

Van Edwards advises testing the relationship gradually rather than getting close too quickly.

Waiting without repeated exposure

A recurring activity creates more realistic opportunities than hoping a close friendship emerges from one meeting.

Is it for you?

Best for

Adults who want a few close friends and can join recurring interest-based settings.

Not ideal for

Treating people as disposable tests or manufacturing stressful situations to provoke a reaction.

From the transcript

Finding friends is like dating.

Vanessa Van Edwards · 2:16:00

I highly recommend go on friendship dates.

Vanessa Van Edwards · 2:16:30

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