E530 Bobby Lee

Bobby Lee and Theo Von dive into a candid conversation about the obstacles they encounter when trying to forge deep connections and practice vulnerability in their romantic relationships.

Challenges in building intimacy

During their discussion, Bobby and Theo share their personal experiences and struggles with intimacy, touching upon their search for meaningful relationships and the difficulties they have faced along the way.

Reflections on past relationships and the quest for vulnerability

Bobby opens up about his previous relationship with Kalila, which lasted a decade, expressing that she was one of the few people with whom he could show his vulnerable side. He admits to having regrets about not being entirely open or as vulnerable with her as he would have liked. There's a sense of self-reproach as he says, "I fucked it up with Kalila," lamenting the missed opportunity to be more transparent about his emotions.

Recognizing and addressing patterns that hinder closeness

As both entertainers, Bobby and Theo confess that they are drawn to the thrill and novelty that come with new relationships. This shared inclination, they realize, could be what stands in the way of achieving true intimac ...

Bobby and Theo share their experiences with substance abuse and recovery

Theo and Bobby openly discuss their personal battles with addiction and the process of recovery, including the challenges they have faced and continue to cope with.

Bobby discusses the allure of using substances and machines to numb difficult emotions and the challenge of maintaining sobriety.

Bobby Lee reflects on his addiction to substances like [restricted term] and the destructive cycle of using drugs to avoid difficult feelings. He talks about his love for substances, contrasting this with the choices of others to avoid them due to fear of addiction. Despite his challenges with substance use, Bobby is currently sober and works with a therapist to confront and experience his emotions directly, rather than numbing them.

Theo expresses concern for Bobby's well-being and encourages him to stay connected to his support network and recovery program.

Theo, while discussing the subject with Bobby, emphasizes the importance of staying connected to support networks and the recovery community. Theo also shares his own considerations regarding drug and alcohol avoidance, suggesting that his natural state isn't his favorite and that there's a temptation to change feelings through substance use.

They explore the prevalence of substance abuse issues in the comedy community and the importance of seeking help.

Bobby and Theo touch upon the prevalence of substance abuse in the comedy community and stress the significance of seeking assistance. Bobby elaborates on his experience attending AA ...

Bobby Lee and Theo Von delve into a heart-to-heart conversation about the complexities of their relationships with their fathers and the lasting impact of their childhood experiences on their individual lives and careers.

Bobby and Theo reflect on their relationships with their fathers and the impact of their upbringings on their lives and careers

Bobby Lee discusses the challenges he faced growing up with a language barrier between him and his father, which severely limited their ability to communicate. He shares that his father did not speak English well, which left Bobby struggling to connect and deprived of typical parental guidance that would usually be conveyed through language.

Bobby shares his struggles with communicating and connecting with his father, who did not speak English well, and how this affected his sense of identity and belonging

Giving an example of their minimalistic exchanges, Bobby explains that his father would only say, “don’t do,” without further explanation, leaving Bobby to navigate life with little guidance. The language gap significantly affected Bobby's sense of identity and belonging, as he found himself unable to bridge the communicative divide between his heritage and his personal experiences.

A particularly poignant moment occurred when Bobby saw his father tear up while listening to Eric Clapton's "Tears in Heaven," a rare instance of emotional connection that transcended their usual communication barriers.

Bobby and Theo empathize with each other's experiences and the challenges of navigating family dynamics, particularly when there is a cultural or language barrier

Theo Von empathizes with Bobby's experiences and expresses a shared understanding of the complexity of family bonds, especially when cultural or linguistic obstacles complicate the relationship. He connects with Bobby by questioning if Bobby misses his father and sharing his own desire to have known his father better, suggesting they both grapple with similar questions of familial connection.

Theo further explores the feelings of complexity by asking Bobby if he ever felt ashamed of his father, touching on the multifaceted emotions that Bobby ...

Bobby Lee and Theo Von delve into the nuanced ecosystem of stand-up comedy, sharing anecdotes about their engagements with famous peers, the rigors of fame, and the tricks to staying inspired.

Bobby and Theo discuss the unique challenges and rewards of being comedians, including navigating fame, fan interactions, and maintaining creative inspiration.

They share stories of encountering famous comedians and the feelings of intimidation, nervousness, and admiration that can arise.

Bobby Lee and Theo Von vividly describe their encounters with comedy giants like Bill Burr, Dave Chappelle, and Chris Rock. They talk about feeling intimidated by these figures, akin to the aftermath of a storm. In particular, Bobby recalls being tongue-tied around them despite a personal history that includes having Burr on his podcast and visiting his home. Bobby's retelling of a chance compliment from Chris at Barnes & Noble humorously hints at the impact such high-profile endorsements can have, credibly narrating the influence of respect from a comedic luminary on his personal life.

They also discuss the dynamics with other stars like Sarah Silverman and Joe Rogan, sharing the delicate tension between self-awareness and the reverence they maintain around such personalities.

Theo reflects on the importance of maintaining boundaries and self-care as their careers have grown, and Bobby offers advice on how to navigate the industry.

The conversation spins towards the topic of self-care, as Theo discusses the necessity of setting boundaries with fans, especially during vulnerable moments or when needing private space, like at the gym. Bobby recounts a weary interaction at a gas station, where he fumbles a fan's photo request out of exhaustion.

As Theo beings up acting, Bobby commends Theo's natural talent, stirring a conversation on the preferences and aspirations they hold within the craft. Bobby recognizes Theo's capacity for kindness amidst the entertainment industry's competitive nature, acknowledging the conscious choice to be nurturing to others.

They explore the role of social media and fan interactions in their lives and the impact it can have on their personal and professional lives.

Reflecting o ...

Bobby Lee and Theo Von engage in a humorous yet insightful conversation about the complexities of their racial and cultural identities, using comedy to navigate and discuss the stereotypes and assumptions that often arise in their personal and professional lives.

Bobby and Theo discuss the complexities of their racial and cultural identities and the ways they have navigated them in their personal and professional lives.

The duo takes a light-hearted approach to discuss serious issues like political affiliations and cultural stereotypes.

They challenge stereotypes and assumptions about Asian Americans and the Asian American experience, particularly in the context of comedy and entertainment.

In discussing the presence of Asians for Trump, Bobby responds humorously to Theo's questioning, rejecting the notion that he is a representative figure for all Asians. They delve into stereotypes as they joke about Bobby's physical resemblance to well-known figures like Kim Jong-un and Benedict Wong, poking fun at the idea that all Asians look alike or come from the "same factory."

Bobby Lee addresses the misconceptions he faces in the comedy industry, recounting times other comedians have bluntly told him that "Asians aren't funny." In a satirical exchange, Theo Von tries to link Bobby Lee’s Asian identity to historical wars involving Asian countries, resulting in a conversation that touches on the common issue of conflating different Asian nationalities.

Theo shares his concerns about the rise of certain drug trends, such as "tranq," within Asian American communities and the need for greater understanding and support.

The conversation takes a turn when Theo mistakenly associates a tranquillizer trend, "tranq," with the Asian community. After some discussion and a fact-check, it becomes evident that the association was misguided, illustrating how random and incorrect associations are often made based on racial or cultural identities.

Bobby and Theo explore the wa ...