Can technology redefine how we approach modern relationships? On the latest episode of CockTales Dirty Discussions, hosts Kiki and Medinah dive into the world of AI-assisted dating advice, putting ChatGPT to work on real-life dilemmas. From relationship status talks to financial contributions, the duo explores whether artificial intelligence can really navigate the complexities of love and commitment.
Before getting into the AI experiment, Kiki and Medinah shared personal updates. Kiki, balancing a packed schedule, has been making use of a walking pad—though not without a coffee-spilling mishap. She also announced that she’ll be speaking at the Podcast Evolutions conference in Chicago, offering insights on transforming podcasts into live experiences.
Meanwhile, Medinah has been focused on real estate and expanding her professional network. She’s also committed to personal growth, working with a trainer and incorporating M Sculpt treatments into her routine. On the family front, she’s planning a beauty-focused birthday weekend for her mom.
The episode featured a discussion on MasterClass, with a particular shoutout to Shan Boodram’s course, The Art of Pleasure. The hosts also promoted Field, an app designed for meeting new people and fostering connections.
Curious about AI’s approach to love and relationships, Kiki and Medinah turned to ChatGPT for advice on a range of scenarios, including:
- Asking a partner about financial contributions
- Navigating Valentine’s Day expectations
- Planning a vacation together
- Defining the relationship
- Requesting help with mortgage payments
- Addressing suspicions of infidelity
- Discussing marriage plans
The AI’s responses were measured, mature, and diplomatic, but the hosts noted that real-life situations often come with heightened emotions that aren’t always as neatly resolved as an AI-generated response.
The episode also highlighted upcoming trips and retreats, including:
- A Sedona, Arizona retreat (August 24-27) centered on The Magic of Big Thinking
- A Barcelona trip in June
- A self-care retreat in March
Listeners were also reminded to take advantage of a MasterClass special offer, which provides 15% off annual memberships through masterclass.com/cocktails.
One of the episode’s most gripping segments involved a listener’s letter detailing an 11-year on-and-off relationship. Issues included:
- A partner reading her private journal without permission
- Communication and trust problems
- A pre-planned, non-refundable trip to Japan
ChatGPT and the hosts unanimously advised the listener to move on, even suggesting transferring the flight ticket to someone else to reclaim the experience.
In a lighthearted moment, the “Indecisive Diane” segment highlighted a tea bus party service in Atlanta. Meanwhile, a listener-submitted story about a disastrous date in rural North Carolina reinforced the importance of setting dating standards and boundaries.
While ChatGPT provided rational and structured advice, the hosts agreed that relationships are messy, unpredictable, and deeply personal—something even the smartest AI can’t fully grasp. Still, for those looking for a level-headed second opinion, it might be worth a try.
