Archive - Ask Polly

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Go to askpolly.substack.com.

Apr 3 • Heather Havrilesky

March 2026

'My Writing Will Never Matter, So Why Can't I Stop Trying?'

Writing is a battle against self-hatred. This is why it will always matter to you, whether your writing matters or not.

Mar 24 • Heather Havrilesky

'NYC Is a Capitalist Nightmare and I'm Miserable Here!'

No one is ever happy, no matter where they live or how rich or successful they are, until they can trade in the shiny fiction of their fantasies for the…

Mar 18 • Heather Havrilesky

'AI Took My Career And Now I Feel Like a Failure!'

Now you can learn to cherish your humanity, which means caring for your neglected body, your impatient, ravenous mind, and your deeply romantic spirit.

Mar 16 • Heather Havrilesky

How to Swap Big, Confusing Career Goals For Small, Fun Experiments

An interview with "Directional Living" author Megan Hellerer

Mar 13 • Heather Havrilesky

'Will I Always Be Codependent?'

As long as you keep living in the future instead of the present? Yes.

Mar 11 • Heather Havrilesky

Do You Punish Yourself Relentlessly?

Supporting yourself emotionally requires trading in bad emotional and physical habits for good ones.

Mar 5 • Heather Havrilesky

'Stop Blaming Women For Being Single!'

Never have, never will!

Mar 2 • Heather Havrilesky

February 2026

'I'm a Stereotypical Single Woman Who Wants a Baby Right Now!'

You can have exactly what you want. Live like it’s already yours.

Feb 23 • Heather Havrilesky

What Sad Surprise Might Set You Free?

My letter to an Ask Polly reader receives an unexpected response!

Feb 19 • Heather Havrilesky

'My Ex Took All of Our Mutual Friends!'

If you never tell anyone how you feel, no one will respect your feelings.

Feb 16 • Heather Havrilesky

How Do You Decide For Yourself?

When you're anxious, self-conscious, and afraid, how do you find your bearings and learn to trust yourself again?

Feb 10 • Heather Havrilesky

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