Podcast Summary

Podcast: Earn Your Leisure
Episode: Should Successful Women Move Differently When Dating?
Date: January 4, 2026
Hosts: Rashad Bilal, Troy Millings (with a female guest/host)
Main Theme:
This episode dives into the unique challenges and nuances that successful women—especially those in the public eye—face in dating and relationships. The discussion uncovers societal double standards, cultural influences, economic disparities, and the impact of social media on the dynamics between men and women, particularly within the Black community.

1. Navigating Relationships as a Public Figure

Key Insight:

• Successful women, especially those with public visibility, often encounter relationship challenges that differ from their male counterparts.
• There’s a perception that women in the spotlight sometimes need to "lower their presence" or manage their ambition to make potential partners more comfortable.

Quotes & Discussion:

• [01:33] "You've been on television for a long time and you've been a public figure... How does that play into relationships?"
• The male host points out that men rarely have to consider how their public profile affects their romantic relationships, whereas women do.
  • [02:36] "Men don't have to deal with that... that's not something that a man ever thinks about. But a woman who is public figure might have to consider that when the dynamics of the relationship might have some level of, you know, imbalance."

2. The Public Eye and Perceptions in Dating

Key Insight:

• Female guest/host discusses misconceptions about her dating life fueled by social media and public speculation.
• The reality of networking as a woman can sometimes be misinterpreted by partners as flirting or inappropriate behavior.
• Success and public recognition can create unique insecurities or discomfort in relationships.

Quotes & Memorable Moments:

• [03:50] "I think it is hard to date as a woman who is in the public eye if you're with somebody who doesn't understand that sometimes networking might look like flirting..."
• She reflects on an incident at a Beyoncé concert where networking could be seen as crossing boundaries, even when innocent, highlighting how public success complicates personal interactions.

3. Compromise vs. Dimming Your Light

Key Insight:

• The importance of maintaining one’s self-worth and confidence in relationships is underscored. The guest stresses the difference between making a partner feel comfortable and compromising personal identity or career success.
• She sets boundaries: “I would never want to be with anybody who wants me to [dim my light].”

Quotes:

• [06:20] "I try to date and make men feel safe when I can... I try to make you feel good. I try to make you feel comfortable, secure, all the things as I would want you to do for me as well. But... I don't think that taking notes looks like me dimming my light."

4. The "Beef" between Black Men and Black Women

Key Insight:

• The host raises the tension and ongoing debates between Black men and women regarding dating expectations and communication.
• There’s a social aspect pointed out by the guest—public perception and social media have amplified divisions that often don’t reflect real-world experiences.

Quotes & Discussion:

• [06:40] "There's something going on and I know y' all have had this debate over and over again with Black men and Black women, where I think we are constantly talking about what one group does versus the other group. And that's why we're in this space where we're constantly knocking heads."
• She mentions being critiqued for appearing "unapproachable" in public because she's on her phone, reflecting stereotypes and expectations placed on Black women.

5. Social Media’s Amplification of Gender and Economic Tensions

Key Insight:

• Social media is acknowledged as a force that can overstate or distort the “battle of the sexes,” making minor or imaginary conflicts seem widespread.
• Economic factors are at the heart of many modern dating issues; disparities in income between Black men and women influence relationship power dynamics.

Quotes & Memorable Moments:

• [08:07] Rashad Bilal: "I hate to be the conspiracy theory guy, but I do think that there is some level of outside influence... a divide and conquer strategy... It's a breakdown in just culture, of American culture overall."
• [08:30] "Most of my clients were Black women. And that's when I realized that Black women was making a lot more money than a lot of Black men. That's a real thing. Yeah, but that definitely causes issues in a relationship... if a woman’s making more money than a man, she’s going to feel on a certain level more empowered."

6. The Reality vs. The Online Echo Chamber

Key Insight:

• Co-hosts question the reality of viral online debates, e.g., 50/50 bill splitting or the so-called "red pill" movement, suggesting these are exaggerated by a vocal minority.

Quotes:

• [10:43] "Most people can't afford to get married. So there's a lot of this is an economic issue where this whole red pill community was birthed out of people that's frustrated..."
• [11:25] "I've never in my life been at a restaurant and seen people... a man tell a woman pay the bill... these hypothetical questions... I've never seen in reality. But like I said, when hurt people hurt people, when you really don't have enough confidence... you're not going to want to talk to a woman because you don't even feel confident in yourself."

7. Final Thoughts

• Relationships between successful women and men are shaped by cultural expectations, economic realities, and amplified online narratives.
• The pressure on women to adapt or shrink their ambition is challenged, and both hosts and guests highlight the need for self-assured, mature communication and mutual respect.

Notable Quotes & Timestamps

• "Men don't have to deal with that... a woman who is public figure might have to consider that..." — Male guest/commentator [02:36]
• "Sometimes networking might look like flirting... I do find that that is uncomfortable." — Female host/guest [03:50]
• "I don't think that taking notes looks like me dimming my light." — Female host/guest [06:20]
• "It's a breakdown in just culture, of American culture overall." — Rashad Bilal [08:10]
• "Most of my clients were Black women... Black women making a lot more money than Black men. That's a real thing." — Rashad Bilal [08:30]
• "Most people can't afford to get married. So there's a lot of this is an economic issue..." — Male guest/commentator [10:43]

Conclusion

This episode of Earn Your Leisure offers an honest, layered discussion about the dating landscape for successful women, touching on fame, self-worth, gender roles, income gaps, and the distorting power of social media. The consensus: while pressures and perceptions exist, maintaining personal confidence and finding mutual respect remain the cornerstones for healthy relationships—no matter your status or success.