EP 285 — How to Approach Dating If You’ve Just Gone Through a Break-Up

from And How Does That Make You Feel? · host Jack Heyworth

Send us Fan MailWhen is the “right” time to start dating again after heartbreak? In this episode, we explore the emotional reality of dating after a break-up — from rebounds and emotional avoidance to loneliness, attachment, and fear of starting over. Learn how to tell whether you’re genuinely ready for a new relationship, the biggest mistakes people make when dating too soon, and how to approach new connections in a healthier, more grounded way without using someone else to escape unresolved pain.

What this episode covers

Send us Fan Mail When is the “right” time to start dating again after heartbreak? In this episode, we explore the emotional reality of dating after a break-up — from rebounds and emotional avoidance to loneliness, attachment, and fear of starting over. Learn how to tell whether you’re genuinely ready for a new relationship, the biggest mistakes people make when dating too soon, and how to approach new connections in a healthier, more grounded way without using someone else to escape unresolve...

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EP 285 — How to Approach Dating If You’ve Just Gone Through a Break-Up

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This episode is 9 minutes long.

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This episode was published on May 21, 2026.

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