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Ask Polly

Heather Havrilesky
Thousands of paid subscribers

Advice and wisdom from Heather Havrilesky, published since 2012 (formerly at The Awl and NY Magazine). Paid subscribers receive 1-2 weekly posts on how to navigate our broken world with compassion, realism, and an open heart.

Platform
Substack
PricingFreemiumPublishesTwice weekly
Issues569Founded7 years agoLast Issue5 days ago
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Latest Issues

Are You Feeling Flat and Numb?

Squirrel Plate (2025) by Heather Havrilesky

I’ve been making pottery for three years now. Sometime during the second year, I realized that my clay was never completely centered. This won’t surprise anyone who’s taught me anything —...

5 days ago
123
16

‘This Break-Up Left Me With So Many Regrets!’

Don’t hide from your own future inside someone else’s crisis.

The Sun In Its Jewel Case (1937), Yves Tanguy

12 days ago
42
10
Paid

“Should I Dump This Guy?”

The Lovers (1929), Yves Tanguy

Dear Polly,

Should I dump this guy I’ve been dating for three months?

I just turned 30 a few months ago. Transparently, my twenties kind of sucked. I was in a career path I didn’t like. I was living...

18 days ago
226
10

Ask Polly Book Club: “Banal Nightmare”

Sleeping (1971), John Wesley

Trauma is a shapeshifter. It plays tricks on our minds, our emotions, our memories. It reformulates our conceptions of ourselves, reshapes reality, distorts our perceptions, unsettles our assumptions....

25 days ago
65
46

‘I’m Not Feeling Excited About The Rest of My Life!’

Many Have Lived (1939), Yves Tanguy

Dear Polly

I’m almost 30 and wow I am not feeling excited about the rest of my life. I know I don’t want children, I don’t desire a romantic relationship or partner and I’m not a particularly dri...

a month ago
358
10

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Authors

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  • Heather Havrilesky

    Advice columnist, cultural critic, author of the memoir Foreverland (Ecco, 2/8/22) +three other books.

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