Dear Chelsea – "Put Some Luxury On It" with Da’Vine Joy Randolph

Podcast: Dear Chelsea
Host: Chelsea Handler (with co-host Kathryn)
Guest: Da’Vine Joy Randolph (Oscar winner, actress in "Eternity")
Date: December 5, 2025

Episode Overview

In this engaging and lively episode, Chelsea Handler sits down with Oscar-winning actress Da’Vine Joy Randolph. The conversation traverses Da’Vine’s personal journey as an artist and woman, the value of authenticity and resilience, the nuances of relationships, and the joys and struggles of trusting one’s intuition. The episode blends hilarious asides, moving insights, and real-world advice for listeners facing crossroads in life, love, and career.

Key Discussion Points & Insights

1. The Power of Authenticity in Personal and Professional Growth

[04:23]-[07:13]

Da’Vine reflects on how embracing her true self, rather than trying to fit into industry molds, led to her biggest successes.
She describes striving to mimic traits of already-successful figures, but ultimately realizing:

"It's here. It's within you. And let those things shine, and the right people will align and attract to those things." — Da’Vine, [06:32]
Chelsea discusses the universe rewarding self-acceptance:

"When it clicks in that you want to be who you really are...the universe starts drumming up all of, like, the positivity in your life when you get on your own team." — Chelsea, [06:56]
The group discusses the concept of “ascension” as women—growing into the person you were meant to be and the importance of ignoring societal hang-ups about age.

2. Early Lessons, Adversity, and Resilience

[09:20]-[13:05]

Da’Vine shares her upbringing, shaped by frequently changing schools and being one of few Black girls in white private institutions.
She notes the emotional resilience and confidence this instilled, imparted largely by her mother.
She also traces her pivot from opera singing to acting after being flunked for making a role her own:

"Adversity. That was my junior year, and it was my mom that was like, you go across that street to the theater department." — Da’Vine, [13:40]
Chelsea and Da’Vine dive into formal training at places like Yale and Oxford, as well as thoughts on Shakespeare, creative genius, and the historic erasure of women’s contributions.

3. Oscar Season & The Industry’s Realities

[16:20]-[18:32]

Da’Vine relives the whirlwind of the Oscar campaign during the Hollywood strikes:

"It was a marathon…It's eight months. It's a very long time." — Da’Vine, [17:35]
On the emotional release of winning and moving on:

"I bawled. Because it was a release. Quiet as it kept. It's done. We're done." — Da’Vine, [18:04]
Discussion about the so-called “Best Actress Curse,” and Da’Vine's feminist boundary about not bringing partners to red carpets:

"I don't ever want them on the red carpet with me... It's all about what we're here for, my job and what I did." — Da’Vine, [19:45]

4. Navigating Love, Dating, and Relationship Dynamics

[20:49]-[25:13]

Da’Vine and Chelsea talk about why dating fellow actors can be a hard “no” (fratty energy!)—and the surprising appeal of dating crew members:

"Crew. That's yummy. Every woman has had a moment while filming..." — Da’Vine, [21:40]
They riff on the “ick” factors of actor dating, the subtle power dynamics with directors, and why female directors are refreshingly efficient.
Chelsea reads listener comments about women opting out of relationships, sparking laughter and solidarity.

5. Reflections on Past Relationships & Breakups

[27:00]-[31:51]

Conversation pivots to Da’Vine’s new film "Eternity," which explores the question: Would you choose to reunite forever with a lost love or stay with the partner you built a life with?
Chelsea and Da’Vine dissect how women and men process breakups differently:

"Women process a breakup and how a man does literally is in reverse order... We go through all the big feelings first...they're in denial." — Da’Vine, [28:13]
They reinforce the importance of intuition and honoring when something is over:

"When we're done, we're done. Because in my mind...I've flushed out every possible option and I've tried my hardest to make this work." — Da’Vine, [29:46]

6. Women’s Intuition: Knowing and Trusting Yourself

[31:51]-[34:30]

Chelsea and Da’Vine praise the deep, often unspoken power of women’s intuition:

"It's one of my favorite things of being a woman. The universe giving us the gift of women's intuition. Oh, God, I love it so much." — Da’Vine, [31:51]
On how to access this intuition, especially if it’s quiet:

"I think, essentially, that might be that people are running from themselves and making themselves busy enough distractions. So they don't have that time to sit with themselves." — Da’Vine, [34:13]

Listener Advice Calls

Caller 1: "How do I survive seven months in a dead-end relationship?"

[40:53]-[43:47]

Summary: “K” realizes her much older fiancé isn’t her person, but plans to wait for her lease to end before leaving.
Advice: Da’Vine and Chelsea unanimously urge her to leave as soon as possible for her own well-being.
Memorable Quote:

"Sell the fucking engagement ring and get that to get out." — Da’Vine, [43:33]

Caller 2: "Can I turn my love of the outdoors into a career?"

[45:17]-[53:16]

Summary: Sharia, in a dull legal assistant job, yearns for a fulfilling outdoors-oriented career.
Advice:
- Start by exploring all outdoor-related jobs and leveraging AI tools like Anthropic.
- Use a business degree for entrepreneurship (e.g., luxury travel guiding, concierge adventures).
- Join or build outdoors communities for networking and exploration.
“Let’s put some luxury on this!” — Da’Vine, [49:25]

Caller 3: "My boyfriend shut down & canceled our trip. What now?"

[57:46]-[66:08]

Summary: Christopher’s three-month romance implodes after his boyfriend reacts with suspicion and silence to a minor event and cancels a planned trip to Europe.
Advice:
- The silent treatment and tracking are toxic, and he should run, not walk, away.
"You can't be with someone who can't communicate and that shuts down like that. He needs to go to therapy, and until he goes to therapy, you have nothing to do with him, period." — Chelsea, [60:09]
- Da’Vine emphasizes gratitude for early red flags:
  
  “Thank you for showing me who you are. Thank you for not wasting my time.” — Da’Vine, [64:25]

Notable Quotes & Memorable Moments

On self-acceptance:

“It's here. It's within you. And let those things shine, and the right people will align and attract to those things.” — Da’Vine, [06:32]
On Oscar campaign exhaustion:

"I bawled. Because it was a release. Quiet as it kept. It's done. We're done. We did this from November to March." — Da’Vine, [18:04]
On recognizing toxic relationships:

"The silent treatment is, like, toxic, bordering on abuse." — Kathryn, [61:10]
On women's intuition:

"It's the truest of you." — Da’Vine, [32:43]
On being a woman in control:

"There's no way that lady's gonna be in this building. I'm like, oh, no, it’s okay [not to ask]." — Da’Vine (on working with Meryl Streep), [66:47]

Timestamps for Key Segments

[04:23] - Da’Vine on authenticity and career breakthroughs
[09:36] - Childhood, identity, and lessons from her parents
[13:05] - From opera to acting, setbacks and pivots
[16:20] - Oscar season, strikes, and the emotional marathon
[19:45] - Boundaries for public/private life after success
[21:40] - Dating in the industry: Why actors are a hard no
[27:00] - "Eternity" film premise and relationship what-ifs
[31:51] - Women’s intuition, learning to trust it
[40:53] - Advice call #1: Leaving a mismatched relationship ASAP
[45:17] - Advice call #2: Creating a fulfilling, outdoor-centered career
[57:46] - Advice call #3: Ending a toxic relationship with clear red flags
[66:47] - Closing reflections, gratitude, and looking ahead

Tone & Style

The episode is candid, witty, and full of warmth. Chelsea’s irreverent humor and Da’Vine’s honesty create a space for real talk about the challenges and beauty of navigating modern womanhood and creative life—sprinkled with memorable laughter and “aha!” moments. The camaraderie and support for listener callers is palpable and uplifting, making this episode equal parts practical advice, therapy session, and hilarious girlfriend catch-up.

For more advice or to listen, search Dear Chelsea wherever you get your podcasts. Da’Vine Joy Randolph’s new film “Eternity” is in theaters now.

Dear Chelsea – "Put Some Luxury On It" with Da’Vine Joy Randolph

Podcast: Dear Chelsea
Host: Chelsea Handler (with co-host Kathryn)
Guest: Da’Vine Joy Randolph (Oscar winner, actress in "Eternity")
Date: December 5, 2025

Episode Overview

Key Discussion Points & Insights

1. The Power of Authenticity in Personal and Professional Growth

[04:23]-[07:13]

Da’Vine reflects on how embracing her true self, rather than trying to fit into industry molds, led to her biggest successes.
She describes striving to mimic traits of already-successful figures, but ultimately realizing:

"It's here. It's within you. And let those things shine, and the right people will align and attract to those things." — Da’Vine, [06:32]
Chelsea discusses the universe rewarding self-acceptance:

"When it clicks in that you want to be who you really are...the universe starts drumming up all of, like, the positivity in your life when you get on your own team." — Chelsea, [06:56]
The group discusses the concept of “ascension” as women—growing into the person you were meant to be and the importance of ignoring societal hang-ups about age.

2. Early Lessons, Adversity, and Resilience

[09:20]-[13:05]

Da’Vine shares her upbringing, shaped by frequently changing schools and being one of few Black girls in white private institutions.
She notes the emotional resilience and confidence this instilled, imparted largely by her mother.
She also traces her pivot from opera singing to acting after being flunked for making a role her own:

"Adversity. That was my junior year, and it was my mom that was like, you go across that street to the theater department." — Da’Vine, [13:40]
Chelsea and Da’Vine dive into formal training at places like Yale and Oxford, as well as thoughts on Shakespeare, creative genius, and the historic erasure of women’s contributions.

3. Oscar Season & The Industry’s Realities

[16:20]-[18:32]

Da’Vine relives the whirlwind of the Oscar campaign during the Hollywood strikes:

"It was a marathon…It's eight months. It's a very long time." — Da’Vine, [17:35]
On the emotional release of winning and moving on:

"I bawled. Because it was a release. Quiet as it kept. It's done. We're done." — Da’Vine, [18:04]
Discussion about the so-called “Best Actress Curse,” and Da’Vine's feminist boundary about not bringing partners to red carpets:

"I don't ever want them on the red carpet with me... It's all about what we're here for, my job and what I did." — Da’Vine, [19:45]

4. Navigating Love, Dating, and Relationship Dynamics

[20:49]-[25:13]

Da’Vine and Chelsea talk about why dating fellow actors can be a hard “no” (fratty energy!)—and the surprising appeal of dating crew members:

"Crew. That's yummy. Every woman has had a moment while filming..." — Da’Vine, [21:40]
They riff on the “ick” factors of actor dating, the subtle power dynamics with directors, and why female directors are refreshingly efficient.
Chelsea reads listener comments about women opting out of relationships, sparking laughter and solidarity.

5. Reflections on Past Relationships & Breakups

[27:00]-[31:51]

Conversation pivots to Da’Vine’s new film "Eternity," which explores the question: Would you choose to reunite forever with a lost love or stay with the partner you built a life with?
Chelsea and Da’Vine dissect how women and men process breakups differently:

"Women process a breakup and how a man does literally is in reverse order... We go through all the big feelings first...they're in denial." — Da’Vine, [28:13]
They reinforce the importance of intuition and honoring when something is over:

"When we're done, we're done. Because in my mind...I've flushed out every possible option and I've tried my hardest to make this work." — Da’Vine, [29:46]

6. Women’s Intuition: Knowing and Trusting Yourself

[31:51]-[34:30]

Chelsea and Da’Vine praise the deep, often unspoken power of women’s intuition:

"It's one of my favorite things of being a woman. The universe giving us the gift of women's intuition. Oh, God, I love it so much." — Da’Vine, [31:51]
On how to access this intuition, especially if it’s quiet:

"I think, essentially, that might be that people are running from themselves and making themselves busy enough distractions. So they don't have that time to sit with themselves." — Da’Vine, [34:13]

Listener Advice Calls

Caller 1: "How do I survive seven months in a dead-end relationship?"

[40:53]-[43:47]

Summary: “K” realizes her much older fiancé isn’t her person, but plans to wait for her lease to end before leaving.
Advice: Da’Vine and Chelsea unanimously urge her to leave as soon as possible for her own well-being.
Memorable Quote:

"Sell the fucking engagement ring and get that to get out." — Da’Vine, [43:33]

Caller 2: "Can I turn my love of the outdoors into a career?"

[45:17]-[53:16]

Summary: Sharia, in a dull legal assistant job, yearns for a fulfilling outdoors-oriented career.
Advice:
- Start by exploring all outdoor-related jobs and leveraging AI tools like Anthropic.
- Use a business degree for entrepreneurship (e.g., luxury travel guiding, concierge adventures).
- Join or build outdoors communities for networking and exploration.
“Let’s put some luxury on this!” — Da’Vine, [49:25]

Caller 3: "My boyfriend shut down & canceled our trip. What now?"

[57:46]-[66:08]

Summary: Christopher’s three-month romance implodes after his boyfriend reacts with suspicion and silence to a minor event and cancels a planned trip to Europe.
Advice:
- The silent treatment and tracking are toxic, and he should run, not walk, away.
"You can't be with someone who can't communicate and that shuts down like that. He needs to go to therapy, and until he goes to therapy, you have nothing to do with him, period." — Chelsea, [60:09]
- Da’Vine emphasizes gratitude for early red flags:
  
  “Thank you for showing me who you are. Thank you for not wasting my time.” — Da’Vine, [64:25]

Notable Quotes & Memorable Moments

On self-acceptance:

“It's here. It's within you. And let those things shine, and the right people will align and attract to those things.” — Da’Vine, [06:32]
On Oscar campaign exhaustion:

"I bawled. Because it was a release. Quiet as it kept. It's done. We're done. We did this from November to March." — Da’Vine, [18:04]
On recognizing toxic relationships:

"The silent treatment is, like, toxic, bordering on abuse." — Kathryn, [61:10]
On women's intuition:

"It's the truest of you." — Da’Vine, [32:43]
On being a woman in control:

"There's no way that lady's gonna be in this building. I'm like, oh, no, it’s okay [not to ask]." — Da’Vine (on working with Meryl Streep), [66:47]

Timestamps for Key Segments

[04:23] - Da’Vine on authenticity and career breakthroughs
[09:36] - Childhood, identity, and lessons from her parents
[13:05] - From opera to acting, setbacks and pivots
[16:20] - Oscar season, strikes, and the emotional marathon
[19:45] - Boundaries for public/private life after success
[21:40] - Dating in the industry: Why actors are a hard no
[27:00] - "Eternity" film premise and relationship what-ifs
[31:51] - Women’s intuition, learning to trust it
[40:53] - Advice call #1: Leaving a mismatched relationship ASAP
[45:17] - Advice call #2: Creating a fulfilling, outdoor-centered career
[57:46] - Advice call #3: Ending a toxic relationship with clear red flags
[66:47] - Closing reflections, gratitude, and looking ahead

Tone & Style

For more advice or to listen, search Dear Chelsea wherever you get your podcasts. Da’Vine Joy Randolph’s new film “Eternity” is in theaters now.

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Put Some Luxury On It with Da’Vine Joy Randolph

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Summary

Dear Chelsea – "Put Some Luxury On It" with Da’Vine Joy Randolph

Episode Overview

Key Discussion Points & Insights

1. The Power of Authenticity in Personal and Professional Growth

2. Early Lessons, Adversity, and Resilience

3. Oscar Season & The Industry’s Realities

4. Navigating Love, Dating, and Relationship Dynamics

5. Reflections on Past Relationships & Breakups

6. Women’s Intuition: Knowing and Trusting Yourself

Listener Advice Calls

Caller 1: "How do I survive seven months in a dead-end relationship?"

Caller 2: "Can I turn my love of the outdoors into a career?"

Caller 3: "My boyfriend shut down & canceled our trip. What now?"

Notable Quotes & Memorable Moments

Timestamps for Key Segments

Tone & Style

Summary

Dear Chelsea – "Put Some Luxury On It" with Da’Vine Joy Randolph

Episode Overview

Key Discussion Points & Insights

1. The Power of Authenticity in Personal and Professional Growth

2. Early Lessons, Adversity, and Resilience

3. Oscar Season & The Industry’s Realities

4. Navigating Love, Dating, and Relationship Dynamics

5. Reflections on Past Relationships & Breakups

6. Women’s Intuition: Knowing and Trusting Yourself

Listener Advice Calls

Caller 1: "How do I survive seven months in a dead-end relationship?"

Caller 2: "Can I turn my love of the outdoors into a career?"

Caller 3: "My boyfriend shut down & canceled our trip. What now?"

Notable Quotes & Memorable Moments

Timestamps for Key Segments

Tone & Style