Ask Polly

Heather Havrilesky
Advice from Heather Havrilesky, author of Ask Polly, formerly of New York Magazine
Created 16 Feb 2020
  • 'My Crush Doesn't Love Me!'
    02 May 2022 71 21
    Horse’s Skull on Blue (1930) by Georgia O’Keeffe Dear Polly, Well I made the classic lesbian mistake of confessing my feelings for a close personal friend and she does not feel the same way. It’s a ta...
  • 'I Don't Know How To Set Boundaries!'
    25 Apr 2022 37 9
    Pond in the Woods (1922) by Georgia O’Keeffe Dear Polly, I’m writing to you because I genuinely don’t know how to set boundaries, assert my needs, show (very real and deep) gratitude, and communicate ...
  • ‘I Made Something Great. What If No One Likes It?’
    21 Apr 2022 35 3
    No. 22 - Special (1916-17) by Georgia O’Keeffe Dear Polly, Longtime reader, all-time screenshotter, and first time asker - I have a question about something that is about to happen to me. I have a lar...
  • ‘I Can’t Do This!’
    18 Apr 2022 53 28
    Taos Mountain, New Mexico (1930) by Georgia O’Keeffe Dear Polly, From the outside, everyone thinks I have it all — the single professional woman making it all on her own. But I am the saddest I have e...
  • 'I Have No Ambition Whatsoever'
    14 Apr 2022 112 44
    Red Hill Form - Badlands, New Mexico (1934) by Georgia O’Keeffe Dear Polly, How do I accept mediocrity? Not in the world (ha! That is a question no philosopher can answer), but in myself? I suppose th...
  • ‘I’m Creatively Blocked!’
    11 Apr 2022 59 8
    Desert Abstraction (Bear Lake) (1931) by Georgia O’Keeffe Dear Polly, The fact that the only way I was able to write something today was when I saw your tweet “Looking for Ask Polly letters about feel...
  • 'Time Moves Too Quickly!'
    06 Apr 2022 101 14
    From the Faraway, Nearby (1937) by Georgia O’Keeffe Today I tried to write something great and I failed. I tried reading old columns for inspiration, but when I came across on this letter about the pr...
  • 'No One Gives Me Credit!'
    04 Apr 2022 66 12
    East River From the 30th Story of the Shelton Hotel (1928) by Georgia O’Keeffe Dear Polly, I’m a long-time reader, first-time writer and your column has pushed me to pursue all my creative endeavors d...
  • 'I'm Turning 30 And Anxiety Is Ruining Me!'
    28 Mar 2022 41 8
    A Street (1926) by Georgia O’Keeffe This letter, which originally ran in The Awl on February 5, 2014, underscores the futility of trying to scold yourself into becoming a different person. The letter ...
  • Should You Talk Less Shit?
    24 Mar 2022 26 12
    City Night (1926) by Georgia O’Keeffe I used to have a lot of imagined enemies. When I was disappointed or angry or ashamed, it felt natural to look around for someone to blame. That’s what happens wh...
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