Interview · moment 21 of 22

Mom's Own Affair, Legalizing Prostitution, and the Documentary Deal

from Seeking Arrangements (with Wendi Starling) · #47

Audio-only archive episode — no video to seek.

5 min

Guest

Wendy compares her situation to her mother leaving her father for a wealthier man, argues for legalized/regulated prostitution to protect trafficking victims, and reveals a documentary crew followed her for a year and a half that's now being shopped with investor backing.

In this bit10 moments
  • 1:07:01Tim's mother was a high-end sex worker in the 1970s at the Plaza Hotel and made enough money to own serious stock.
  • 1:07:16Tim treats sex work as a business like any other—some people do it well, but young people without development shouldn't jump in unprepared.
  • 1:07:56Legalizing prostitution makes sense for high-priced escorts, but most prostitution involves trafficking and exploitation from third-world countries.
  • 1:09:09Tim argues legalization would actually reduce trafficking because victims could report abuse to police instead of staying in the shadows.
  • 1:10:18The guest describes her arrangement as simple and above-board, with clients free to end things anytime.
  • 1:10:41She's experienced heartbreak from clients stopping contact, which hurt more than when they simply moved on to other women.
  • 1:10:57This kind of arrangement could only work with wealthy men who have time constraints but want something consensual and real.
  • 1:11:16Every now and then the guest will sleep with a struggling comedian just to make sure she's still got it.
  • 1:11:39Tim asks about her comedy ambitions; she's pitching her live show Glamour Press to different networks and working on two scripted shows.
  • 1:11:59A documentary about her is set to release in theaters between October and January, which she plans to tour off once it comes out.
Mentioned here

Glamour Pressprostitution legalizationdark webPlaza Hotel

All 22 moments in this episode →