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James Bennett Wins AI-Assisted 'Performative Male' Pageant at San Francisco's Alamo Square

A custom AI prescreen signaled how a TikTok meme has jumped to real-life pageants.

Pondering women's rights in preparation for the look-alike contest. Photo by Jordan Montero.
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Matt Jereza dons a Charli XCX Brat shirt while being judged by an all-women panel during a performative male contest at Alamo Square Park in San Francisco.
Steven Zhang reveals a cutout for his phones in a book after receiving a tot bag for placing top five during a performative male contest at Alamo Square Park in San Francisco.

Overview

  • Hundreds gathered at Alamo Square Park on Aug. 22 as James Arthur Bennett V was crowned winner in a crowded contest that drew more than 1,000 RSVPs.
  • The organizers confirmed a preliminary judging round used a custom model at performative.lol to score aesthetic signifiers such as matcha, Labubu toys and feminist literature before narrowing to a top 26 and then 10.
  • The event was assembled in just over a week via Partiful by a group led by Kake Jin, operated on roughly a $2,000 budget and featured micro-sponsorships from Dex by Thirdlayer, AI Valley, Ditto AI and Kiss of Matcha.
  • Turnout forced an earlier start and caused QR-code entry snags, yet the spectacle played well with onlookers, with gift cards distributed and a small trophy awarded to the winner.
  • Bennett said he would donate any cash prize to women’s shelters and Gaza, and the park pageant was framed as part of a broader, mostly playful Gen Z trend that has staged similar contests from Seattle to Los Angeles.