EP 288 — How to Approach Dating If You’ve Been Single for Years

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

Send us Fan MailWhat happens when you’ve been single for so long that dating starts to feel unfamiliar, uncomfortable, or emotionally overwhelming? In this episode, we explore how long-term singleness changes your nervous system, routines, expectations, and emotional defences — and why re-entering dating can feel far more vulnerable than people realise. Learn the biggest mistakes people make after years alone, how to stop turning dating into a reflection of your self-worth, and how to approach new relationships in a healthier, slower, and more grounded way without losing yourself in the process.

What this episode covers

Send us Fan Mail What happens when you’ve been single for so long that dating starts to feel unfamiliar, uncomfortable, or emotionally overwhelming? In this episode, we explore how long-term singleness changes your nervous system, routines, expectations, and emotional defences — and why re-entering dating can feel far more vulnerable than people realise. Learn the biggest mistakes people make after years alone, how to stop turning dating into a reflection of your self-worth, and how to approa...

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EP 288 — How to Approach Dating If You’ve Been Single for Years

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This episode is 8 minutes long.

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This episode was published on May 23, 2026.

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