Finding a Halloween costume that will totally wow can be a deceptively tricky task. Do you go with something classic like a cat or do you opt for a super topical idea like “Netflix and chill.” It seems no one know the perils of finding the right outfit quite like Lena Dunham. In the most recent issue of her newsletter Lenny Letter, Lena shared a few of her most memorable Halloween costume fails and explains a little bit about why each went so very wrong.


Here Lena remembers wanting to be a “fancy lady” (left) and a secretary (right). Of the former costume, Lena explains, “I went home early, weeping, after this rude bully called Peter N. told me ‘Fancy lady isn’t even a real costume.’” Disagree.

She pins her desire to be a super ’90s secretary on her love for Nick at Night where “secretaries were always running in and out of those vintage sitcoms with something important to say. ‘Mr. Grant, there’s an urgent call!'” Lena may consider these fails, but if you ask us they’re both pretty solid picks.


Lena admits that she didn’t really dress up in high school because she didn’t have anyone to dress up with, but decided to get back into the Halloween game during her freshman year in college. She says, “I went as a mermaid, this time in a store-bought costume made of itchy sparkly rayon rather than an ass-tail made by my dad. I was pretty sure this look would lead to the loss of my virginity, but mermaids don’t have vaginas, and painting my face blue was perhaps a bridge too far.”

After she had her big break in show biz, Lena spent Halloween in 2011 at a party with a bunch of film industry dudes. To impress the crowd, Lena dressed as the comedian Louis CK. She says her evening in this costume involved running into an ex and some girl telling her, “‘You even did padding and everything!’ After which she proceeded to pinch my actual stomach flesh. Hard.”

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After sharing all of her costume-related struggles, Lena shared a photo of what she’s planning on dressing up as this year: a Planned Parenthood doctor. Lena has been a major supporter of the organization for a long time and of this outfit she says, “This year, I think I may have finally nailed it. I’m going as something newsy, sexy and cool.”

What is your biggest Halloween fail? Share a photo with us in the comments below or tag us on Instagram.

(Photos via Lena Dunham/Lenny Letter)