Worst Behavior: Vacation Reveals EVERYTHING ft. Kitty Roberts

Worst Behavior: Vacation Reveals EVERYTHING ft. Kitty Roberts

From CockTales: Dirty Discussions by Kiki Said So & Medinah Monroe

May 9, 2026 · 1h 7m · Episode 491

About this episode

The episode features Kitty Roberts discussing luxury travel, relationship dynamics, and the impact of vacations on dating and self-discovery.

This week, we’re joined by Kitty Roberts — founder of Worst Behavior Tour — for a conversation about luxury travel, relationship drama, sexual curiosity, girls trips, and why everybody is NOT built for international travel. We talk about: the reality of hosting trips to places like Jamaica, Bali, Thailand, and the Philippines relationship drama that unfolds on vacation why some couples should NEVER travel together balancing freedom, trust, and boundaries while dating sex clubs, open-minded relationships, and curiosity travel scams and red flags people miss when booking group trips why travel changes the way you see dating, men, and yourself the pressure women face when dating publicly Meg Thee Stallion’s breakup discourse and why women are exhausted with cheating culture Kitty also shares stories from hosting trips to Hedonism II, wild travel moments, why communication matters before couples trips, and the difference between traveling for fun versus traveling for healing, freedom, and self-discovery. Whether you’re planning your next girls trip, thinking about booking a luxury group experience, or trying to decide if your relationship can survive a vacation together…this episode…

People in this episode

Hosts: Kiki Said So, Medinah Monroe

Guest: Kitty Roberts

Topics covered

  • luxury travel
  • relationship drama
  • sexual curiosity
  • girls trips
  • international travel
  • communication in relationships
  • dating culture

Keywords

  • travel
  • relationships
  • vacation
  • communication
  • dating
  • girls trip
  • sexual curiosity
  • travel scams
  • Hedonism II

Sponsors

Drive Boost - VB Health, FEELD, BROOKLYN BEDDING

Mentioned in this episode

Organizations: Worst Behavior Tour

Places: Jamaica, Bali, Thailand, Philippines, Hedonism II

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