Podcast Summary: The HoneyDew with Ryan Sickler Episode 340: Esther Steinberg: Bagels, Ballots, and The Tampa Toss Release Date: June 23, 2025

Introduction

In Episode 340 of The HoneyDew with Ryan Sickler, host Ryan Sickler welcomes comedian Esther Steinberg to share her unique and often humorous experiences growing up in a family deeply entrenched in both comedy and law. The episode delves into Esther's tumultuous family dynamics, her father's unconventional career path, and the challenges she faced both personally and professionally.

Family Background

Esther Steinberg paints a vivid picture of her upbringing in Tampa, Florida, highlighting the complexities of her family life. She is the youngest of three daughters, with two older sisters who have distinct relationships with her.

• Siblings: Esther shares that one sister is her best friend, while the other is someone she is not on speaking terms with due to untreated mental illness, leading to an environment where Esther often became the peacemaker.

  • Quote: “Untreated mental illness, you know, it's tough. That prepped me for life because that sister was always walking on eggshells.” [04:12]

• Parents:

  • Mother: An Israeli-born engineer working for Honeywell, Esther describes her mother as a strong role model who balanced her engineering career with periods of being a stay-at-home mom.
  • Father: A Tampa native and the youngest graduate from the University of Florida Law School, Esther's father navigated the worlds of law and comedy, often blurring the lines between the two.
    • Quote: “He was very difficult—hard to talk to, and balancing his law career with his passion for comedy.” [08:11]

Father's Ventures: Bagel Boudoir and Comedy

Esther details her father's entrepreneurial spirit and his foray into the restaurant business with the creation of the Bagel Boudoir, a controversial breakfast establishment akin to Hooters.

• Bagel Boudoir:

  • Concept: The restaurant featured strippers serving breakfast, a novel and unconventional idea that ultimately failed due to poor food quality and negative public perception.
    • Quote: “It was a breakfast Hooters. Bagels and logs and eggs that were...real gross.” [16:01]
  • Media Attention: The venture attracted negative media attention, leading to smear campaigns against her father, branding him as a "Bagel pimp."
    • Quote: “They called him the Naked Bagel. The people named it.” [26:34]

• Comedy Club Ownership:

  • Comedy Corner: Esther's father was part-owner of a comedy club during the early careers of now-famous comedians like Jeff Foxworthy and Larry the Cable Guy.
    • Quote: “He was part-owner of a comedy club called Comedy Corner, featuring comedians who were just starting out.” [09:29]
  • Struggles: Despite his involvement, his stand-up career never took off, leaving him to focus more on his legal practice.

Political Campaigns and Smear Campaigns

Esther recounts her father's persistent attempts to enter politics, including multiple unsuccessful campaigns for state legislator, Congress, and even the presidency.

• Campaign Efforts:

  • Strategies: Her father employed aggressive campaigning tactics, including hiring Esther and her sisters to collect signatures and promoting himself through various media channels.
    • Quote: “He asked me to stand outside the library and collect signatures. You need like 6,000 signatures or $50,000.” [25:15]
  • Smear Ads: Opponents launched derogatory smear ads focusing on his failed restaurant venture and alleged association with the controversial practice of dwarf tossing.
    • Quote: “The smear ads came out...they called him the Naked Bagel and the Bagel pimp.” [26:34]

• Dwarf Tossing Controversy:

  • Legal Battle: Esther's father fought against the legality of dwarf tossing, an event some considered abusive, to advocate for those who wanted to participate willingly.
    • Quote: “He wanted to overthrow dwarf tossing so he can be thrown.” [28:15]
  • Public Perception: Despite his intentions, the campaign was met with resistance from the dwarf community and led to further negative publicity.
    • Quote: “He was on the radio stating, 'I'm a dwarf, and I want to be tossed.'” [28:36]

Family Dynamics and Personal Struggles

The episode explores the emotional strain within Esther's family, particularly the emotional absence of her father and the challenges Esther faced in her personal life.

• Emotional Absence:

  • Father's Demeanor: Esther describes her father as emotionally unavailable, rarely expressing pride or engaging in deep conversations.
    • Quote: “He never asks me how I’m feeling. ‘How are you doing?’ was always followed by jokes.” [40:07]
  • Impact on Esther: This led Esther to seek validation through academic excellence and extracurricular activities to mend her relationship with her parents.
    • Quote: “I ended up graduating with straight A's because they told me they wouldn't love me otherwise.” [56:09]

• Esther's Own Challenges:

  • Postpartum Experience: Esther recounts a traumatic experience during her second childbirth, where an overly affectionate male doctor made her uncomfortable, leading her to file a formal complaint.
    • Quote: “He was excessively rubbing my hands and saying, ‘Relax, relax.’ It made me want to kill myself.” [46:36]
  • Therapy and Recovery: She discusses her journey through therapy to address the emotional scars left by both her upbringing and her childbirth experience.
    • Quote: “I'm here for you. But I also was like, I recovered. I'm good. I'm fine.” [50:40]

Esther's Career and Personal Life

Esther talks about her path to becoming a comedian, drawing inspiration from her father's failed attempts and using humor as a coping mechanism.

• Education and Career:

  • College: Despite her father's lackluster support, Esther pursued higher education at NYU to follow her passion for comedy and acting.
    • Quote: “I graduated the top of my class and wanted to go to NYU to be an actress and do stand-up.” [57:07]
  • Comedy: Esther uses her personal experiences, including her family's quirks and her father's antics, as material for her stand-up routines.
    • Quote: “I write jokes about my father, saying, 'My dad is autistic,' and how he never shows emotion.” [57:49]

• Marriage and Relationships:

  • Husband: Esther is married to a man who contrasts sharply with her father—emotionally intelligent and supportive, providing a balance to her family's dynamics.
    • Quote: “I married a man who always wanted a dad who wasn't choking up at every Shabbat dinner.” [58:20]
  • Parenting: As a mother of two, Esther navigates the challenges of postpartum depression while maintaining her role as a comedian and wife.
    • Quote: “I'm postpartum with my second child...trying to play this game while being postpartum.” [40:04]

Conclusion

Episode 340 offers a candid and humorous glimpse into Esther Steinberg's life, highlighting the intricate balance between comedy and personal struggle. Through her storytelling, Esther underscores the importance of resilience, the healing power of humor, and the complexities of familial relationships. The episode culminates in Esther reflecting on her experiences and offering advice to her younger self, emphasizing the value of embracing life's freedoms before family responsibilities take precedence.

• Final Advice:

  • Embrace Freedom: Esther advises her younger self to enjoy life’s freedoms before the responsibilities of motherhood take over.
    • Quote: “Embrace those and enjoy life before kids. That freedom before kids is like, can we bottle that up and sell it?” [60:39]

• Promotion: In the closing moments, Esther promotes her latest work, Smear Campaign, available on Amazon and Apple, along with her merchandise and upcoming performances in Las Vegas.

  • Quote: “We got Smear Campaign, it's my baby. You can follow me on Instagram, Esther Steinberg.” [61:50]

Notable Quotes with Timestamps

• Family Dynamics: “Untreated mental illness, you know, it's tough. That prepped me for life because that sister was always walking on eggshells.” [04:12]
• Comedy Inspiration: “I always say that these are the stories behind the storytellers.” [03:23]
• Bagel Boudoir Failure: “The food was really gross and that's why it didn't work.” [16:36]
• Political Smear Campaign: “They called him the Naked Bagel. The people named it.” [26:34]
• Emotional Absence: “He never asks me how I’m feeling. ‘How are you doing?’ was always followed by jokes.” [40:07]
• Postpartum Trauma: “He was excessively rubbing my hands and saying, ‘Relax, relax.’ It made me want to kill myself.” [46:36]
• Advice to Younger Self: “Embrace those and enjoy life before kids. That freedom before kids is like, can we bottle that up and sell it?” [60:39]

Key Takeaways

• Humor as a Coping Mechanism: Both Ryan and Esther utilize comedy to navigate and cope with life's lowlights, emphasizing laughter's therapeutic role.
• Complex Family Relationships: The episode highlights the challenges of growing up with emotionally distant parents and the impact it has on personal development.
• Persistence Amid Failure: Esther's father's relentless pursuit of comedy and politics, despite repeated failures, underscores themes of resilience and the cost of ambition.
• Personal Healing: Esther's openness about her postpartum experience and her journey through therapy sheds light on the importance of addressing personal trauma and seeking support.

The HoneyDew with Ryan Sickler continues to deliver engaging and heartfelt storytelling, blending humor with genuine insights into the human experience. Episode 340 with Esther Steinberg is a testament to the power of laughter in overcoming adversity and the enduring bonds of family.