Seeking Arrangements

Seeking Arrangements

From Rehash by Rehash

May 4, 2026 · 58 min

About this episode

The episode explores the origins and implications of Seeking Arrangements, a sugar babying website, and its impact on dating dynamics.

Today, male virgins inject peptides into their asses, dissociate on Kick, and disavow women. But twenty years ago, they simply took matters into their own hands and developed websites where they could BUY women! The year was 2006, and Brandon Wade, chud of the first order and master of self-written puff pieces, decided enough was enough and developed Seeking Arrangements - a sugar babying website where wealthy older men could meet broke younger women. It’s a site most women have visited at least once, or twice, or three times, in their most destitute college years. One that has all the sexual suggestiveness, intimacy, and transactionality of sex work but with less of the stigma. But, like OnlyFans, Seeking Arrangements has attempted to distance itself from all sexual connotations in recent years, posing instead as a “luxury dating site.” In this episode, Hannah and Maia look back on Seeking Arrangements’ heyday. They discuss the extreme theatre of heterosexual dating dynamics, and ask whether Wade was right that all little girls dream of finding a man with a high paying job, or if the site simply found its popularity alongside crumbling social infrastructure. Tangents include…

People in this episode

Hosts: Hannah, Maia

Topics covered

  • sugar babying
  • dating dynamics
  • sexual suggestiveness
  • social infrastructure
  • online dating

Keywords

  • sugar baby
  • Seeking Arrangements
  • Brandon Wade
  • dating
  • OnlyFans
  • Feeld
  • college
  • transactionality

Sponsors

Qui

Mentioned in this episode

Organizations: Seeking Arrangements, OnlyFans, Feeld

Books & works: Rehash

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