ReLiving Single – Episode Summary: "Max Gets Her Groove Back"

Podcast: ReLiving Single
Episode: Max Gets Her Groove Back featuring Anwar White
Date: September 10, 2025
Hosts: Erika Alexander & Kim Coles
Special Guest: Anwar White

Overview

This episode dives into Living Single’s Season 1, Episode 17: “The Hand That Robs the Cradle.” Hosts Erika Alexander (Maxine Shaw) and Kim Coles (Synclaire James), alongside guest dating coach Anwar White, discuss the iconic "May-December" romance between Max and a much younger college student, Brendan (portrayed by Terrence Howard in an early role). The conversation explores age-gap relationships, societal double standards, sexual dynamics, dating advice for Black and brown women, and the cultural impact of Living Single.

Episode Breakdown & Key Discussion Points

Revisiting "The Hand That Robs the Cradle" (03:05–13:00)

• Plot Recap:

  • A Story: Max dates Brendan, a 7-years-younger NYU freshman, and tries to keep it from her friends.
  • B Story: Regine throws an advertiser's gala on a tight budget.
  • C Story: Kyle grapples with needing (and refusing) glasses due to vanity.

• Behind-the-Scenes Nostalgia:

  • Erika and Kim recall working with a young Terrence Howard, praising his charisma and later success.
  • Discussion about being “man magnets,” humorously touching on their own experiences, and how intelligence is a key draw for Max (06:39).

Quote:
"Max is a man magnet because… she doesn’t need them, by the way, she loves sex. But... she’s also attracted to people who have intelligence. And they are attracted to her because of her mind." – Kim Coles (06:39)

Exploring Age-Gap Relationships: On the Show & In Real Life (07:28–13:52)

• Nuanced Talk on Age Differences:

  • The hosts examine why age differences feel more pronounced at certain life stages.
  • Comfort with relationships changes as people mature; “seven years at some other time might be absolutely fine.” (09:43)

• Max and Brendan’s Chemistry:

  • Kim discusses the performative nature of chemistry onscreen, acknowledging the awkwardness of social expectations and “getting caught out like that.” (11:17)
  • The importance of agency and living life without always feeling accountable to others’ opinions.

• Societal Double Standards:

  • Older women with younger men are labeled “cougars,” with connotations very different from older men dating younger women.
  • Erika jokes: “Actually, I don't like cougar. I say that I'm an ocelot. Cause I can't run that fast.” (00:18 & 40:55)

• Sexual Politics & Humor:

  • Erika and Kim riff on stereotypes of male and female sexual peaks, with plenty of laughter and playful banter.

Directing & Performing Living Single (14:36–17:53)

• Behind the Scenes:
  • Deep dive into filming dynamics: why kitchen scenes felt so alive and theatrical, importance of physical staging, and director Ellen Gitelson’s attention to camera work.
  • Improv within the script: Emphasis on sticking to written lines for comedic timing but finding freshness in performance.

Quote:
"Our improv is mostly inside a performance… practice knowing the lines and then delivering them like you don't know them." – Kim Coles (16:33)

The Big Confrontation & Emotional Maturity (21:28–23:53)

• Powerful Scene Discussion:
  • Max ends things with Brendan, recognizing the emotional complexity of their age gap, and waiting for a time when they're better matched.
  • Praising Terrence Howard’s performance and the scene's mature, non-blaming tone.

Quote:
"So you two in this scene are looking at your responsibility. It's like, I like you. I'm falling for you. It doesn't seem like the right timing. And so it's a very mature conversation without blaming or naming or shaming. Just like, see you later, maybe." – Erika Alexander (25:56)

May-December Romance Reflections & Life Lessons (27:05–30:26)

• Age, Sex, and Confidence:
  • Erika and Kim openly discuss changing sexual confidence with age, comfort in one’s body, and the expanded “buffet” of life and love experiences.
  • Emphasize embracing freedom and self-acceptance that often comes in later decades.

Quote:
"I am much more comfortable naked now than I ever was in my 20s." – Erika Alexander (28:08)

The Reverb: Expert Break Down with Anwar White (34:46–59:48)

Introducing Anwar White (35:05)

• Dating coach, creator of Get Your Guy Coaching, and “dating fairy godbrother” with a focus on helping Black and brown women find healthy relationships.

Is Age Gap Still Taboo? (35:44–37:45)

• Societal taboos persist mainly for age gaps greater than 10 years, but women are increasingly “choosers, not waiting to be chosen.”
• Most of Anwar’s clients are with men 3–6 years younger and he actively recommends Black women date younger men.

Quote:
_"I actually recommend that Black women specifically get with younger men. And one, because y'all don't age for sure, so y'all gonna look the same age anyway." – Anwar White (36:14)**

Navigating Pressures & Power Imbalances (37:45–39:43)

• Discusses insecurities: running out of time, fear of being left for younger partners, family and societal judgment.
• Warns against secret "DL" dating that leads to isolation and lower relationship satisfaction:
  “The most dangerous thing that you can do because then you're in isolation … You need what I call your love jury.” (39:32)

Key Factors in Age-Gap Dating (41:23–42:52)

• Alignment on non-negotiables (kids, career, lifestyle).
• Manage power dynamics and financial balance, have strong boundaries, be comfortable with aging and shifting roles.

Cultural and Gendered Conditioning (44:53–46:19)

• Explains extra challenges for Black women: being raised stoic, difficulty expressing vulnerability, lack of boundary modeling—all essential to healthy modern relationships.

Biology, Sexual Peaks, and Energy Shifts (46:35–48:56)

• Discusses sexual and emotional peaks, why women in their 40s–50s may find younger partners more appealing.
• Highlights changing masculine/feminine energy as both men and women age:
  “There’s a beautiful thing that happens around 45 and 50… Women are having more testosterone and men are losing theirs. There’s a switch of the masculine and feminine energy.” (48:56)

Media’s Role & Representation (49:15–50:43)

• Living Single portrayed the awkwardness and beauty of age-gap romances with authenticity and humor, especially capturing how such relationships can help Black women reconnect with fun and playfulness.

Internet Dating Debates & Archetypes (50:43–58:39)

• Anwar critiques modern debates about “what do you bring to the table” as unhelpful power struggles and prescribes seeking partners with emotional skills, not just opinions.
• Assigns Living Single characters dating archetypes:
  • Max: Emotionally unavailable queen—needs to lean into vulnerability.
  • Khadijah: “Boss lady”—should learn to ask for help.
  • Regine: High-maintenance queen seeking validation—must identify self-worth.
  • Sinclair: Kind romantic—needs to set boundaries.

Quote:
"Ultimately, … the biggest opportunity for Sinclair was setting boundaries. … She would be attracting a lot of toxic and narcissistic men that would take her kindness for weakness." – Anwar White (56:50)

Recommendations for Listeners (58:15–59:48)

• Therapy and self-work are encouraged, especially bell hooks’ All About Love.
• Identifies the value in seeking wisdom from elders and maintaining a supportive "love jury."

Notable Quotes & Moments

• "She’s not robbing the cradle. She’s challenging the system. She’s challenging the status quo." – Kim Coles (60:03)
• "Do I sound like a whore now? … Well, a little bit, but I listen and I don't judge." – Kim Coles & Erika Alexander, joking about sexual confidence (29:52)
• "Call the police. Call the popo. Call the popo on Terrence." – Kim Coles (26:55), on age reversals in life vs. story

Fun Behind-the-Scenes Fan Q&A (60:01–63:39)

• Discovery: The iconic “Woo hoo” heard at episode’s close is voiced not by any cast member, but by series creator Yvette Lee Bowser (61:01).
• The famous opening credits dance: Filmed to a “jamming” track—no one recalls exactly what song it was, but cast all agree they “threw down.” (62:00–62:48)

Timestamps for Key Segments

• 00:04–02:22 – Banter, age-gap romance jokes
• 03:05–13:00 – Episode overview & scene analysis
• 14:36–17:53 – Directing/acting deep dive
• 21:28–25:56 – Max and Brendan’s maturity and parting scene
• 27:05–30:26 – Confidence with age, sexual empowerment
• 34:46–59:48 – Reverb: In-depth talk with Anwar White on age gaps, dating, archetypes
• 60:01–63:39 – Listener Q&A: fan questions, behind-the-scenes lore

Episode Tone

Warm, cheeky, and unfiltered, with tons of humor, honesty, and thoughtful analysis. Both hosts remain candid and irreverent. Anwar brings compassion, directness, and a sense of inclusion for Black women’s dating experiences.

Takeaways for Listeners

• Age-gap relationships bring opportunities and unique challenges—honest conversations, alignment, and support systems are key.
• Living Single continues to create space for nuanced conversations about sex, love, aging, and Black women’s choices.
• Vulnerability, self-work, and intergenerational support are essential for finding healthy, happy relationships.
• The hosts’ camaraderie and lived experience, backed by expert advice from Anwar White, provide both laughs and real wisdom.

Not to Miss:

• Erika and Kim’s unfiltered asides on sex, confidence, and showbiz timelines (especially 28:03–30:26)
• Anwar’s “love archetype” breakdown (54:04–57:26)
• The story behind the “woo-hoo” and Living Single’s legacy dance scenes (60:58–63:39)