Mike Birbiglia's Working It Out – Episode 165: Rachel Feinstein Returns: Everything She Says Could Be a Bit

Release Date: April 7, 2025
Host: Mike Birbiglia
Guest: Rachel Feinstein

Rachel Feinstein returns to Mike Birbiglia's Working It Out for her third appearance, bringing her trademark comedic energy and a wealth of personal anecdotes. This episode delves deep into Rachel’s past relationships, her marriage to firefighter Pete, her experiences living in unconventional living situations, and her ongoing journey in comedy and motherhood.

1. Relationship with Husband Pete

Rachel begins by highlighting the unique dynamic of her marriage to Pete, emphasizing the freedom and trust that defines their relationship.

• Rachel Feinstein (00:06): "That he doesn't have any notes for me. And then I have a level of freedom that I can have not had with other relationships."

Mike probes further into Rachel's past relationships to contrast them with her current marriage.

• Mike Birbiglia (00:13): "Oh, interesting. What were the notes you got in other relationships?"
• Rachel Feinstein (00:16): "Well, before him, I was with a guy that was, like, extremely jealous. Like, you know, alarmingly jealous."

Rachel candidly shares her experience with a previous boyfriend who exhibited extreme jealousy, even going as far as installing spyware on her phone.

• Rachel Feinstein (00:22): "Like, he put spyware on my phone. Is that enough manifesting for you?"

Mike humorously remarks on Rachel's candidness, appreciating her ability to blend humor with uncomfortable topics.

• Mike Birbiglia (00:36): "That is the voice of the great Rachel Feinstein. Man, I love this episode."

2. Past Relationships and Living Situations

Rachel recounts her tumultuous past relationships and the unconventional living situations she found herself in, showcasing her resilience and comedic prowess.

Extreme Jealousy and Spyware Incident

Rachel elaborates on the extent of her ex-boyfriend's jealousy, highlighting how it affected her personal and professional life.

• Rachel Feinstein (05:00): "It's hardcore. It's debilitating. You know, I'm teaming with it."

She humorously discusses how her ADD (Attention Deficit Disorder) might have contributed to her ex-boyfriend's suspicions.

• Rachel Feinstein (04:50): "I'm, like, teaming with ADD. Like, I mean, I've had it since I was 11."

Living in "Squalor" with Other Comedians

Rachel shares stories about living with fellow comedians Sherrod Small and Tony Rock in a cramped, basement-style apartment dubbed "Squalor."

• Rachel Feinstein (13:06): "We used to call our apartment Squalor because we lived in squalor."

She paints a vivid picture of the chaotic environment, complete with friends frequently using her bed and the challenges of maintaining personal boundaries.

• Rachel Feinstein (13:41): "They were going to harass him and call croissant, right? Like all croissant."

3. Comedy Material and Personal Anecdotes

Throughout the episode, Rachel provides a treasure trove of comedic material drawn from her life experiences, enhancing the podcast's humor and depth.

Doctor Interaction Gone Awry

Rachel recounts a humorous yet unsettling interaction with her doctor, where he inadvertently made inappropriate jokes during a mammogram appointment.

• Rachel Feinstein (04:54): "He goes, yankees are Mets."

• Rachel Feinstein (07:57): "You got one boob."

This segment highlights Rachel's ability to find humor in uncomfortable and tense situations.

Mother-in-Law Dynamics

Rachel discusses the complexities of her relationship with her mother-in-law, who views her comedic storytelling with skepticism and subtle disdain.

• Rachel Feinstein (17:09): "She doesn't really watch me. And she'll say it to me and she... like a foul rumor she has no way of substantiating."

• Mike Birbiglia (19:21): "How do you unpack that with your own life?"

Rachel reflects on the vulnerability of sharing personal stories that intertwine with her family's perceptions.

4. Motherhood and Preschool Challenges

Transitioning to motherhood, Rachel humorously navigates the trials of managing her child’s preschool experience while maintaining her comedic edge.

• Rachel Feinstein (49:24): "One of them was because I bring her late a few days a week."

She exaggeratedly portrays the seriousness with which preschool administration treats minor issues, adding a comedic twist to everyday parenting challenges.

• Rachel Feinstein (50:12): "Who wants to fucking sit around the Magna Tiles? No."

5. Comedy Collaboration and Creative Process

Rachel and Mike discuss the intersection of their creative processes, the importance of surrounding oneself with honest feedback, and the continuous evolution of their comedic material.

• Mike Birbiglia (10:19): "You have comedians, where everything you say kind of could be a bit. And you kind of... feel like you need to surround yourself with the most amount of people who point out, actually, that could be a bit."

• Rachel Feinstein (29:58): "He's just kind of like, sure, whatever."

Rachel appreciates Pete's non-confrontational nature, which contrasts sharply with her previous relationships and facilitates a more supportive creative environment.

6. Navigating Uncomfortable Topics with Humor

Rachel skillfully balances discussing sensitive and personal topics with humor, making the conversation both engaging and relatable.

• Rachel Feinstein (08:00): "He was doing a bit. I told him I think I might be dying."

• Rachel Feinstein (17:55): "What am I gonna do? That's on you. My kids pick your nose during nap class."

Her ability to weave personal struggles into comedic narratives underscores her unique talent as a comedian.

7. Current Projects and Philanthropy

Towards the end of the episode, Rachel touches upon her current endeavors, including writing a book and her involvement with the nonprofit Friends of Firefighters, which provides mental health services to firefighters and their families.

• Rachel Feinstein (51:43): "I'm going to do a big benefit soon because it's called Friends of Firefighters..."

Mike supports her philanthropic efforts and encourages listeners to engage with her cause.

8. Closing Remarks and Future Endeavors

As the episode concludes, Mike highlights upcoming projects and provides shout-outs to Rachel's ongoing tour and specials, reinforcing the strong rapport between host and guest.

• Mike Birbiglia (52:31): "Rachel Feinstein, you're the funniest. Come back. Come back to the podcast all the time."

Notable Quotes:

• Rachel Feinstein (00:22): "Like, he put spyware on my phone. Is that enough manifesting for you?"
• Rachel Feinstein (07:53): "He was doing a bit. I told him I think I might be dying."
• Rachel Feinstein (14:56): "You can't have croissants running up in you."
• Rachel Feinstein (29:58): "He's just kind of like, sure, whatever."
• Rachel Feinstein (51:43): "I'm going to do a big benefit soon because it's called Friends of Firefighters..."

Conclusion:

Episode 165 of Mike Birbiglia's Working It Out with Rachel Feinstein is a rich tapestry of humor, personal revelation, and insightful discussion. Rachel's ability to transform her life's chaotic and sometimes troubling moments into compelling comedy provides listeners with both laughter and a deeper understanding of her as an artist and individual. This episode not only entertains but also inspires, showcasing the therapeutic and connective power of humor.