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Ask Polly

Advice for the messy, specific problems dating and life actually throw at you.

Substack Dating Weekly Updated Sep 2026

About

Ask Polly, written by Heather Havrilesky, answers reader-submitted questions about dating, breakups, and the general difficulty of being a person, with long, personal, occasionally profane responses rather than tidy bullet-point advice.

It's less a how-to-date guide than a genuinely literary advice column, closer to reading a smart friend think out loud than consuming a listicle of dating tips.

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