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Not Even To Tennis With The Kushners?

Not Even To Tennis With The Kushners?

Karlie Kloss and The US Open

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Madeline Hill
Aug 22, 2025
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Impersonal Foul
Impersonal Foul
Not Even To Tennis With The Kushners?
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If Bravo and ESPN had a baby, it would be Impersonal Foul. This newsletter is free, but consider becoming a paying subscriber for $6/month to support the work that I’m doing.

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Maybe it’s because I read forums on The Fashion Spot in high school or maybe it’s because I was a teen model, but I’ve always been fascinated by Karlie Kloss.

I remember when she made her runway debut as a Calvin Klein exclusive (iykyk) and when that one Italian Vogue cover shot by Steven Meisel came out.

I remember when Kloss launched Kode With Klossy, a nonprofit dedicated to getting more young girls interested in STEM.

And—of course—I remember when Kloss started dating Joshua Kushner, founder and managing partner of Thrive Capital and co-founder of Oscar Health (that insurance company with great branding and not so great actual coverage).

When Kloss started dating Kushner in 2012, I saw paparazzi photos of the pair at Knicks games, but there was something about spotting them at the US Open that always stuck out to me.

Is it because I am a life-long tennis fan and am waiting for a brand to send me to the US Open this year? Not NO….

The first US Open they were spotted at together was round 1 in 2014. Kloss and Kushner were in a suite and she was wearing those damn hoops that I always associate with the famous courtside photos of Kloss and Ms. Taylor Alison Swift.

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