Diary of a CEO: Best Episodes for Relationships, Dating & Love Advice

Updated March 2026 · 8 min read · By the team at diaryofceo.online

Steven Bartlett has turned The Diary of a CEO into the most important podcast for anyone trying to understand modern relationships. From toxic dating patterns to building lasting love, the show has hosted the world's leading voices on human connection. We've ranked the episodes that will genuinely change how you approach relationships.

Whether you're navigating a breakup, trying to find the right partner, or strengthening a long-term relationship, these episodes deliver science-backed, emotionally honest advice you won't find anywhere else.

The Top Relationship Episodes, Ranked

1. Matthew Hussey — "The 3 Texts That Make Any Man Chase You"

Dating coach Matthew Hussey's appearance is the most-watched relationship episode in DOAC history for good reason. He dismantles the "playing hard to get" myth and replaces it with a framework built on genuine confidence. His concept of "high value" behaviour — investing in people who invest back — reframes the entire dating game.

Hussey explains that the biggest mistake people make isn't choosing the wrong person; it's staying too long with someone who shows you exactly who they are. His practical advice on texting, first dates, and reading signals has helped millions of listeners stop wasting time on the wrong people.

Key Takeaway: Stop auditing your worth based on someone else's inability to see it. Confidence isn't about performing — it's about genuinely believing you'll be fine either way.

2. Esther Perel — "Why People Cheat & How to Affair-Proof Your Relationship"

World-renowned psychotherapist Esther Perel brings decades of couples therapy experience to one of the most nuanced conversations Steven has ever had. She challenges the black-and-white view of infidelity, explaining that affairs are often about self-discovery rather than the partner. Her framework distinguishes between the "crisis of desire" and the "crisis of identity."

Perel's insight that modern relationships carry an impossible burden — we expect our partner to be our best friend, co-parent, intellectual equal, and erotic lover — is a genuine paradigm shift. She argues for "erotic intelligence": the ability to maintain mystery and desire within committed love.

Key Takeaway: The quality of your relationships determines the quality of your life. Stop expecting one person to fulfil every emotional need — build a rich ecosystem of connection.

3. Jay Shetty — "The 4 Types of People You Need to Cut Off Immediately"

Former monk turned relationship coach Jay Shetty brings a spiritual but practical lens to understanding toxic relationships. His framework categorising people as "drains" or "radiators" gives listeners an immediate tool for auditing their social circle. He explains how childhood attachment patterns create adult relationship dysfunction — and more importantly, how to break the cycle.

Shetty's advice on setting boundaries without guilt resonated deeply with the DOAC audience. His distinction between loneliness (a state of mind) and solitude (a choice) reframes the fear that drives people into bad relationships.

Key Takeaway: You cannot change someone who doesn't see a problem with their behaviour. Boundaries aren't walls — they're filters that let the right people in.

4. Dr. Robert Glover — "Why 'Nice Guys' Fail at Relationships"

Author of No More Mr. Nice Guy, Dr. Glover explains why people-pleasing behaviour destroys relationships rather than building them. "Nice" behaviour, he argues, is actually a covert contract: "I'll do things for you so you'll love me." When the contract isn't honoured, resentment builds silently.

This episode is essential listening for anyone who has ever felt taken for granted. Glover's advice to express needs directly — rather than hoping your partner will read your mind — is deceptively simple but transformational.

Key Takeaway: Expressing your needs clearly isn't selfish — it's the foundation of every healthy relationship. People can't meet needs they don't know about.

5. Logan Ury — "How to Not Die Alone: The Science of Finding Love"

Behavioural scientist and Hinge's Director of Relationship Science, Logan Ury brings data to the dating conversation. She identifies three "dating tendencies" — the Romanticiser, the Maximiser, and the Hesitater — that keep people single. Her research shows that the best predictor of long-term compatibility isn't butterflies on the first date; it's how someone makes you feel about yourself over time.

Key Takeaway: Stop looking for instant chemistry. The strongest relationships are built on emotional stability, not fireworks. Give slow-burn connections at least three dates.

Common Themes Across These Episodes

Attachment Styles Matter More Than You Think

Nearly every relationship guest on DOAC references attachment theory. Whether it's Hussey explaining anxious-avoidant dynamics or Shetty discussing how childhood shapes adult love, the message is clear: understanding your attachment style is the single most impactful thing you can do for your love life. The guests consistently recommend reading Attached by Amir Levine as a starting point.

Communication Is a Skill, Not a Talent

Perel, Glover, and Ury all emphasise that great communicators aren't born — they practise. The specific tools vary (Perel recommends "turning towards" bids for connection; Glover advocates direct requests), but the principle is universal: say what you mean, listen to understand, and stop keeping score.

You Attract What You Are, Not What You Want

Every guest circles back to the same truth: the relationship you have with yourself sets the ceiling for every other relationship. Shetty's meditation practices, Hussey's confidence exercises, and Ury's self-awareness frameworks all point toward the same goal — becoming the person your ideal partner would want to be with.

How to Get the Most From These Episodes

Don't just listen — implement. Here's a simple framework:

  1. Listen once for understanding. Don't multitask. Give it your full attention.
  2. Write down three actionable insights. Not quotes — actions you'll take this week.
  3. Share one insight with a friend. Teaching solidifies learning.
  4. Revisit after 30 days. You'll hear different things when your situation changes.

Explore the full DOAC episode library and listener guides at
diaryofceo.online