rant · moment 3 of 23

Paying a Webcam Girl and the Weekend That Ruined It

from #178 - Secret Society | The Tim Dillon Show · #178

4 min

They discuss the fantasy of webcam relationships and a documentary about a man who paid a cam girl for years only for an in-person weekend visit to feel deeply awkward.

In this bit4 moments
  • Tim and a friend debate the fantasy of trying to seduce a webcam girl after paying her.
  • A documentary about a man who paid a webcam girl for years before she finally spent a weekend with him—an experience that felt weird for both of them.
  • Online rapport differs fundamentally from in-person connection; a full weekend together is harder than a single dinner date.
  • Tim once went on a date with a girl who asked him to buy her groceries and then moved into his bed without progressing further physically.

All 23 moments in this episode →