In this powerful episode, we hear from three men navigating dating after heartbreak, rejection, and personal transformation. Tiago, a newly single dad, opens up about falling hard for a woman fresh out of her own divorce—and the grief of not being chosen. Brady asks how to confidently start conversations in person and online. And Brandon vulnerably explores a repeating pattern of giving too much and being left behind.

If you’ve ever asked yourself: Why does love feel so one-sided? or Am I stuck in the same cycle?—this one is for you. We offer honest answers, emotional insight, and real strategies to move forward without closing your heart.

💬 Topics we cover:

• Rebound heartbreak and emotional availability

• How to start conversations that actually connect

• The over-functioning pattern that leaves good men feeling unseen

• Building confidence without performing

• When to try again—and when to walk away for good

Whether you're fresh out of a relationship or ready to rewrite your love story, you'll walk away with tools, validation, and hope.

Submission 1: Tiago (00:00)
After a 14-year marriage, Tiago dives into dating again—only to fall for a woman not yet over her own divorce. We explore why emotionally available men often feel heartbreak more deeply, and how to stop trying to prove your worth to someone who isn’t ready to choose you back.

Submission 2: Brady (21:45)
Brady asks a common question: How do I start the conversation—on apps or in person—without being awkward or overthinking it? We break down what actually matters in first impressions (hint: it’s not cleverness), and how curiosity beats performance every time.

Submission 3: Brandon (38:10)
Brandon is done chasing women who don’t choose him back. We unpack the anxious attachment pattern of over-giving, why it keeps showing up, and how to lead with discernment instead of devotion in future relationships.

Self-Made Man Dating Journal Self-Made Man: Dating Journal for Men | Track Confidence, Patterns & Reflections | Build Self-Mastery, Emotional Intelligence & Intentional Dating Habits | Personal Growth Journal

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