Navigating Friendship in a Digital Age

This chapter delves into the evolving nature of friendships as individuals transition into their thirties, emphasizing the importance of communication and emotional investment. It also examines the impact of social media on these relationships, advocating for a more intentional approach to fostering meaningful connections amid the complexities of modern life.

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Modern life has made friendship feel more confusing, fragile, and isolating than ever. In this episode, journalist and author Anna Goldfarb joins us to unpack the paradox of modern friendship — why we’re lonelier despite being more connected, and what we can do to build stronger, more fulfilling relationships.

Anna shares her “Triple D” framework (Desire, Diligence, Delight) and breaks down the hidden architecture of great friendships: clear aboutness, healthy compartmentalization, emotional maturity, and the courage to reconnect.

Whether you’re tired of being everyone’s unpaid therapist or simply wondering how to revive a drifting connection, this episode gives you the practical tools and emotional insight to reset your social life — no cringe required.

What to Listen For

[00:00] Why affection alone isn’t enough for deep friendship

[00:01:09] What’s changed about adult friendships — and why we’re feeling more disconnected

[00:04:16] The hidden cost of unlimited choice and hyper-individualism

[00:08:07] Active vs. nostalgic friendships: how to tell the difference

[00:11:19] Every great friendship has an “About” — and here’s how to find yours

[00:14:39] 6 hard truths about friendship (and how to stop blaming yourself)

[00:23:01] Why emotional maturity is the new social skillset

[00:33:56] The Triple D framework for building strong friendships

[00:44:10] How to avoid being an unpaid therapist (and stop pushing people away)

[00:52:34] The Friendship Cleanse: reset your network with clarity and care

Episode Takeaways:

Connection isn’t about quantity — it’s about clear shared meaning. Find your friendship “About.”
It’s okay to compartmentalize your relationships. Not every friend needs to be your everything.
Friendships require maintenance. If it matters, don’t let the silence stretch too long.
Maturity means asking: am I showing up the way I want to be treated?
Most people want to reconnect. They’re just waiting on someone to go first.
Make time for delight. Reignite friendships by creating new shared memories — not just rehashing old ones.

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Resources from this Episode

Anna Goldfarb on Substack

Anna Goldfarb on Instagram

Modern Friendship: How to Nurture Our Most Valued Connections

Check in with AJ and Johnny!