Pretty, Funny & Single: Are We Addicted to the Wrong Men? ft. Keysha E.

Pretty, Funny & Single: Are We Addicted to the Wrong Men? ft. Keysha E.

Author: Kiki Said So & Medinah Monroe March 20, 2026 Duration: 1:26:24
This week, we’re joined by comedian Keysha E for a fun, slightly chaotic, and very honest conversation about dating, attraction, and figuring out what we actually want. From celebrity crush debates to whether chemistry is just a toxic addiction (yes, we said it), we get into the difference between a good partner and a good time.

We also talk about pretty privilege in comedy, dating in Atlanta vs. LA, finances in relationships, and why “safe” might not be as boring as it sounds. Plus, we answer a listener question about feeling lost in life and share a CockTales story that involves a FaceTime mishap you absolutely don’t want to experience 😭

We kick things off getting to know Keysha—from her journey into comedy to what it’s like being an attractive woman in a space where people don’t always expect you to be funny . The conversation quickly turns into dating (of course), where we unpack everything from celebrity crushes and short king debates to the reality of dating in Atlanta versus Los Angeles.

We get into a deeper conversation about chemistry vs. compatibility—are we chasing that instant spark because it feels good, or because we’ve been conditioned to? And are we overlooking genuinely good partners because they don’t give us that “high”?

We also talk about marriage, financial conversations in relationships, independence, and what it looks like to build with someone instead of waiting until everything is perfect.

In this week’s advice segment, we respond to a listener who’s questioning the point of life and whether everything feels like a performance. It turns into a real conversation about purpose, slowing down, and figuring out what actually brings you joy.

And of course, we wrap things up with CockTales—where Keysha shares a story involving FaceTime that goes very, very left.


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Grab a drink and get comfortable. CockTales: Dirty Discussions is that unfiltered conversation happening in the corner of your favorite bar, hosted by friends Kiki Said So and Medinah Monroe. With one navigating single life and the other rooted in a long-term relationship, their perspectives clash and complement in the most honest ways. This isn't a clinical advice show; it's a raw, comedic, and deeply personal journal of what modern dating, sex, and relationships actually feel like on the ground, specifically through the lens of life in Atlanta. Each episode feels like you’re pulling up a chair to their table as they dissect their latest encounters, frustrations, and triumphs with zero censorship. The laughter is genuine, the stories are real, and the discussions go to places most are too polite to mention. You’ll find this podcast lives in the messy, human intersection of society, culture, and personal revelation, all served with a hefty side of comedy. Tune in for the kind of candid talk that makes you nod in recognition, laugh out loud, and maybe even rethink your own approach to the complicated sea of love and connection.
Author: Language: English Episodes: 100

CockTales: Dirty Discussions
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