Podcast Summary: "My D*ck is Exhausted with Boom Boom 'Jeff' Hiller"

Episode Information:

• Title: My D*ck is Exhausted with Boom Boom "Jeff" Hiller
• Release Date: July 3, 2025
• Host/Author: iHeartPodcasts, hosted by Chelsea Handler and co-host Catherine Law
• Guest: Jeff Hiller (known as Boom Boom Hiller)

1. Introduction to Jeff Hiller

[02:18] Katherine: "We have a really fun guest today... his name is Jeff Hiller."

[03:38] Katherine: Introduces Jeff Hiller, affectionately dubbed "Boom Boom," highlighting his popularity from the HBO show Somebody Somewhere.

2. Upbringing and Early Struggles

Jeff shares his experiences growing up in Texas as a gay boy, dealing with bullying, and how these challenges shaped his resilience and humor.

[04:34] Jeff Hiller: "I think that's why I'm funny now. I think that was like a self coping mechanism, you know, to try and make you laugh so you won't hit me."

[05:04] Katherine: "Your childhood in school and the torturing or the teasing and the bullying just sounded terrible."

Jeff reflects on how bullying, while harsh, inadvertently built his character and comedic talent.

[07:17] Jeff Hiller: "I think I could have gotten sufficient character with just, you know, 80% less torture."

3. Career and Book: Actress of a Certain Age

Jeff discusses his book, Actress of a Certain Age: My 20-Year Trail to Overnight Success, sharing humorous and humiliating stories from his auditions and early career.

[04:11] Katherine: "Boom Boom, otherwise known as Jeff Hiller, has a new book called Actress of a certain age. My 20-year trail to Overnight Success."

[10:33] Katherine: "There is two scenes that I'm thinking of right off the top of my head... waxing the butthole."

[10:45] Jeff Hiller: Recounts a particularly embarrassing audition scene involving laser hair removal on an actor's butthole, humorously titled "Leather Cheerio."

4. Navigating Success and Timelines

The hosts and Jeff delve into societal expectations around success timelines, emphasizing flexibility and personal growth over rigid benchmarks.

[13:45] Katherine: "People have these timelines... I always thought, as long as by 32, if I've got my... that's so silly and so stupid."

[14:12] Jeff Hiller: "Nobody wants to hire you when you're like, please, please hire me. I've only got this one season left."

They discuss how success often arrives unpredictably and the importance of adapting expectations.

5. Personal Growth and Self-Reflection

Jeff shares insights into his journey of self-improvement, emphasizing compassion for others and self-compassion.

[22:17] Jeff Hiller: "My dick is also exhausted."

[23:31] Katherine: Reflects on her own experiences with intervening in conflicts, highlighting personal growth and reliability.

[24:04] Katherine: "I have compassion for everyone, but I'm not ever compassionate to me, towards yourself."

6. Relationships and Emotional Maturity

The conversation shifts to the dynamics of long-term relationships, the necessity of communication, and emotional growth.

[28:28] Jeff Hiller: "You've got to work at it. You have to like, check in with people."

[29:16] Katherine: "I have to carve out that kind of time."

They discuss the complexities of maintaining a healthy relationship over time, including setting aside dedicated time and addressing annoyances constructively.

7. Audience Q&A and Advice Segment

The hosts and Jeff tackle listener questions, offering candid and humorous advice.

a. Rob’s Dilemma: Overwhelmed by Mother's Religious Gifts

Question Summary: Rob, a 36-year-old gay man from a conservative evangelical family, is frustrated with his mother continuously sending him Bibles and religious items despite his progressive lifestyle.

[38:03] Katherine: Suggests having a direct and gentle conversation with his mother to express his feelings.

[39:33] Jeff Hiller: "A polite, tactful way of saying, I think I'm good on Bibles is maybe enough."

b. Timothy’s Relationship Crisis in the Netherlands

Question Summary: Timothy, moving from South Africa to the Netherlands with his less emotionally mature boyfriend, faces challenges in their relationship, including poor sex life and the suggestion of an open relationship.

[41:39] Jeff Hiller: Advises focusing on communication, setting boundaries, and seeking couples therapy to address underlying issues.

[46:04] Katherine: Encourages Timothy to frame therapy as a means to improve their sex life, thereby making it less intimidating for his boyfriend.

c. Judith’s Family Complexities: Mother Remarrying a Step-Sister’s Husband

Question Summary: Judith, a 47-year-old single mom, is distressed by her 72-year-old mother marrying her stepsister's socially difficult husband, Larry, leading to familial tensions.

[62:00] Katherine: Recommends setting boundaries and asserting her feelings by choosing not to engage with Larry while maintaining a loving relationship with her mother.

[66:34] Jeff Hiller: "It's clear. Your mom has terrible taste in men."

[69:35] Katherine: "You've done the work. You got this. Don't do it. Be nice to your mother. Tell her you love her and that you're always open to seeing her. But you're not interested in hanging out with Larry."

8. Conclusion

The episode wraps up with reflective banter between the hosts and Jeff, emphasizing the importance of self-awareness, setting boundaries, and proactive communication in personal relationships.

[73:16] Jeff Hiller: "Thank you. Seriously, thank you."

[73:52] Katherine: Highlights upcoming performances and encourages listeners to support Jeff by ordering his book.

Notable Quotes:

• Jeff Hiller [05:35]: "I think that's why I'm funny now. I think that was like a self coping mechanism..."

• Katherine [14:12]: "I always had that in my head based on her success, which is so silly and so stupid."

• Jeff Hiller [22:17]: "My dick is also exhausted."

• Judith [69:30]: "I'm not a people pleaser anymore... I don't want to put myself in a situation where I'm not being real."

Key Takeaways:

• Resilience Through Adversity: Jeff's experiences with bullying in his youth fostered his comedic talent and personal strength.

• Flexible Success Timelines: Success doesn't adhere to a strict timeline; personal growth and adaptability are crucial.

• Importance of Self-Compassion: Being kind to oneself is as vital as showing compassion to others.

• Healthy Relationships Require Work: Open communication, setting boundaries, and dedicating time are essential for maintaining long-term relationships.

• Assertive Boundaries with Family: It's important to assert personal boundaries, even with family members, to maintain healthy relationships and personal well-being.

This episode of Dear Chelsea offers a blend of humor, personal anecdotes, and heartfelt advice, making it both entertaining and insightful for listeners navigating their own personal and professional challenges.