Club Shay Shay – Best Of Truth After Dark: Kevin Gates, G Herbo, Joy Taylor, Shan Boodram, & More!

Release Date: November 24, 2025
Host: Shannon Sharpe (iHeartPodcasts and Shay Shay Media)

Episode Overview

This "Best Of Truth After Dark" episode compiles highlights from dynamic, after-hours conversations with guests ranging from athletes like Kevin Gates and G Herbo to culture commentators Joy Taylor and intimacy expert Shan Boodram. Host Shannon Sharpe and a rotating cast of co-hosts and guests engage in wide-ranging, unfiltered discussions on modern dating, sex and relationships, gender roles, double standards, loyalty, communication, and what it really means to love, compromise, and grow.

With both humor and candor, the participants share personal stories, controversial opinions, and provocative questions that spark lively debates, punctuated by moments of vulnerability and introspective wisdom.

Note: Ads and non-content have been excluded. Timestamps (MM:SS) for key moments.

Key Discussion Points and Insights

1. The “Dubai Offer” Debate & Extreme Proposals

• Topic: Would you endure a humiliating act for a life-changing amount of money?
• Participants joke about women being paid large sums for outrageous deeds in Dubai, sparking a debate on personal boundaries and the price of dignity.
• Female host asserts she wouldn't do degrading acts "for a million dollars" (02:19), underscoring her limit:

  “No, I don't think I could... I would be traumatized. Not for a million.” (02:09–02:19)

• Guests bounce around hypothetical offers, highlighting societal fascination with scandal and money versus ethics.

2. Age Gaps and Dating Preferences

• Topic: The acceptable age range in dating, & why women are gravitating toward younger men.
• Discussion reveals a trend: women in their 30s and late 30s are finding that “younger men… come with it” and show more intentionality (05:01).
• Female host playfully notes she would only show up with a much older man “if he’s got a plane,” and friends should “treat him real good, act like everything is normal.” (06:09–06:39)
• Conversation shifts to stereotypes and appeal of older men:

  “Older men have great stories.”
  “They're very confident… they appreciate you.”
  (06:43–07:07)

• Humorous bants about the physical realities (“I can't have sex with an old wrinkly penis. I'm so scared!”) (07:07–07:23)

3. Porn, Masturbation, and Sexual Energy (feat. Kevin Gates)

• Kevin Gates challenges societal taboos around masturbation and porn:

  "Have you ever watched porn and masturbated and celebrated another man's success?... You know that’s self mutilation?" (08:04–08:25)

• Gates shares that a mentor taught him about “sex transmutation”—funneling sexual energy into purpose and creativity instead of pleasure-seeking (08:29–09:23).
• He values “intellectual intercourse” and mental chemistry, likening great conversations to “mental safari” and “porn.” (09:51–10:05)

4. Gender Roles & Relationship Double Standards

• Topic: Do size and bedroom skills matter for women?
  • Host: “It does to a certain degree… if you just have a little thing…” (13:00–13:07)
  • Honest talk about sexual compatibility and how connection goes beyond just the physical (13:38–14:29).
• Why do men’s needs seem so "simple" and women’s so "expensive"?
  • Guest: “A man’s needs are free. A woman’s needs cost money.” (15:00)
  • Host suggests women are raised to get their needs met but not to meet a man’s needs (15:32–16:34).

5. Children, Age, and “Cooked” Women

• Topic: Stigma around women in their 30s with no kids.
  • Guest quips: “Most women who don’t got no kids in their mid-30s are cooked.” (18:34)
  • Host rebuts passionately:

    “Am I cooked or am I smart?... I'm so sorry that I didn't want to be another statistic, but I'm cooked? I think I'm very fucking smart, actually.” (19:17–20:33)

6. Gender, Cheating, and Loyalty (Paul Pierce Segment)

• Viral Take: “Men need to cheat on their women to find out if they really love them.” (41:50)
  • Guest and hosts unpack why cheating is often seen as a loyalty test, questioning if it proves anything other than insecurity or manipulation.
  • Host: “You're creating distrust in your relationship for no reason.” (46:11)
  • Pierce tries to clarify: “I don't respect the woman that will be okay with me cheating.” (47:47)
  • Conversation points out the contradiction between wanting loyalty and not respecting someone who tolerates cheating (48:26–49:30).

7. Racial Dynamics in Dating

• Discussion on why some Black men date white women (21:07–23:07):
  • Guest: “White women make themselves more available... They show up... they linger...” (22:24–22:42)
  • Host counters with the broader social context:

    “As soon as they don't get their way... you are an N word, hard er. And that's the truth...” (23:09–24:15)

  • Call for celebrating preference without denigrating Black women:

    “If you want to mess with a white woman and an Asian woman and this woman, go do that and leave us out of the conversation.” (35:39)

8. Honesty, Boundaries, and Respect

• “Give me the list” Dilemma:
  • Cam Newton’s controversial demand for his partner’s sexual history list is dissected (50:17–54:42).
  • Host: “I'm not gonna have my man in front of someone...that I know I used to mess with... I'm gonna tell him.” (53:29)
  • Guests debate whether it’s fair for women to be expected to give their list if men don’t reciprocate (55:20–56:37).
• On new partners and learning/changing routines:
  • Shan Boodram advocates humility:

    “Stop wishing for genies and mind readers… everyone is different… you want somebody who's humble and asks questions and is curious.” (36:45–38:00)

9. Compromise and Accountability in Relationships

• Co-host: “Men always have to do a little bit more compromising… swallow the pill a little bit more.” (25:05–25:46)
• Ongoing dialogue about who apologizes more and the importance of direct communication over ego (26:42–28:15).

10. Marrying "the Hoe" vs. the "Housewife"

• Superhead (Karrine Steffans) Clip:
  • Should men “marry the hoe” instead of cheating with them?
  • Guest: “Just because sex is cool... that don’t mean that’s gonna last forever. When they get down to like... bringing some substance to the table… that’s what men look for long term.” (30:02–31:46)

Notable Quotes by Segment & Speaker

• On Transmuting Sexual Energy:
  • Kevin Gates [08:29]:

    “If you pleasure driven, you develop addictions. If you purpose driven, you develop riches. Not just wealth of the pocket, but of the heart and mind.”

• On Dating Outlets and Race:
  • Host [23:09]:

    "As soon as they don't get their way... you are an N word, hard er. And that's the truth..."

• On Women Being ‘Cooked’ Without Kids:
  • Host [19:17]:

    "Am I cooked or am I smart?... I'm so sorry that I didn't want to be another statistic, but I'm cooked? I think I'm very fucking smart, actually."

• On Cheating as a Test:
  • Host [46:11]:

    “You're creating distrust in your relationship for no reason. You are creating tests that don't need to be created.”

• On Compromise:
  • Co-host [25:46]:

    “I've always had to just kind of sorry. All right, yeah, let's go. Because I'm driving the ship…”

• On Learning Sexual Skills:
  • Shan Boodram [36:45]:

    “Stop wishing for genies and mind readers. I want someone who just knows what I like... Everyone is different... you want somebody who's humble and asks questions and is curious...”

Notable/Memorable Moments with Timestamps

• [02:09] – “I would be traumatized. Not for a million.” — Female host debates the Dubai myth.
• [05:01] – “25 year old men are where it's at. ... treat you like you're a goddess.”
• [08:29] – Kevin Gates explains the concept of sex transmutation.
• [13:00] – Discussion: “Does size matter to women?”
• [18:34] – Guest jokes about mid-30s childless women being “cooked;” host’s passionate rebuttal.
• [21:07] – “If your woman is white, you could cheat.” The viral Paul Pierce clip is unpacked.
• [23:09] – Host clarifies dangers for Black men dating white women and preferences.
• [30:02] – Should men “marry the hoe”? Long-term substance vs. sexual excitement.
• [36:45] – Shan Boodram’s “stop wishing for mind readers” sexual communication advice.
• [41:50] – Paul Pierce’s viral “cheat to test her love” theory.
• [50:17] – Cam Newton’s “I want the list” relationship demand.

Tone and Style

The episode is raw, unapologetically honest, and playful yet often poignant. There’s a seamless blend of candid banter, hard truths, and laughter—sometimes brash but always deeply rooted in real experiences and cultural context. Speakers bring streetwise humor, introspection, and a willingness to challenge both societal and personal norms.

Final Thoughts

The “Best Of Truth After Dark” episode showcases the podcast’s unique chemistry: guests and hosts are comfortable bringing their real selves, wrestling with layered topics—sex, money, race, gender, and love—without shying from discomfort or complexity. The conversation offers plenty to think about (and plenty to laugh at), making it a compelling sampler for both new and returning listeners.