Heavyweight: Episode "2025 Update: Leif + A Conversation with Anna Konkle"
Release Date: July 17, 2025
Introduction
In this compelling episode of Heavyweight, host Jonathan Goldstein undertakes a heartfelt journey to reconnect with Leif, a middle school crush who mysteriously vanished from his life at age 14. Alongside this personal quest, Jonathan engages in an insightful conversation with Anna Konkle, co-creator of the acclaimed show Pen15, delving into the emotional challenges of revisiting one's adolescent years as an adult.
Jonathan's Journey to Find Leif
Revisiting Old Flames
Jonathan begins by recounting his deep-seated crush on Leif during junior high. "[...] Leif was my crush, the object of my junior high obsession. I still Google him occasionally, but he's completely absent from the Internet" (03:04). Determined to find closure, Jonathan discovers a possible address for Leif in Arizona through a public records database, igniting hope and anxiety.
Enlisting Help
Unsure of how to approach Leif directly, Jonathan turns to Khalilah Holt for assistance. Together, they craft a plan to reach out, reflecting Jonathan's lingering insecurities and desire for answers about their unresolved past.
Conversations with Friends: Lucia and Karina
Memory Lane with Lucia
Jonathan shares nostalgic conversations with his friend Lucia, reminiscing about their shared memories of Leif. Lucia provides emotional support, affirming Jonathan's worth:
Lucia Holt: "No, I mean, I'm sure you wrote. You're a very good writer and a thoughtful person, so I'm sure the way you approached it was good." (15:08).
Uncovering the Past with Karina
Reaching out to Karina, another mutual friend, Jonathan uncovers old IM exchanges that reveal Leif's struggle with illness during their adolescent years. This discovery shifts Jonathan's perspective:
Jonathan Goldstein: "Leif had some sort of illness the whole time I knew him, but I never knew how sick he was or what he was even sick with." (31:36).
The Zoom Meeting with Leif
Reconnecting After Years
Jonathan finally connects with Leif via Zoom. The conversation is awkward yet sincere:
Despite the years that have passed, Jonathan finds comfort in Leif's familiar demeanor. However, the conversation leaves him with more questions than answers, particularly regarding why Leif never pursued a relationship on Valentine's Day.
Leif's Revelation
Leif reveals his battle with Crohn's disease, providing context to his past behavior:
Leif: "I was, like, very, very, very sick. I was, like, in the process, essentially, of getting diagnosed with Crohn's disease." (31:28).
This revelation alleviates some of Jonathan's feelings of inadequacy, as he realizes that Leif's lack of interest was influenced by his health struggles rather than personal rejection.
Reflections on Self-worth and Relationships
Emotional Aftermath
Post-conversation, Jonathan grapples with lingering self-doubt despite having a supportive boyfriend, Sam:
Jonathan Goldstein: "I am, in fact, undateable." (35:17).
His interactions with friends and family reveal a persistent struggle with self-esteem and the impact of unresolved adolescent experiences on his present relationships.
Anna Konkle's Insight: Creating Pen15
Behind the Scenes of Pen15
Transitioning to the second segment, Jonathan interviews Anna Konkle about her show Pen15, which artistically portrays middle school experiences through adult actresses. Anna discusses the emotional toll of recreating such a vulnerable period:
Anna Konkle: "I mean, it was so humiliating." (43:25).
Emotional Challenges
Anna shares the personal difficulties of acting as a younger version of herself, including dealing with her father's cancer diagnosis during production. The blend of personal trauma and professional responsibilities adds depth to her storytelling.
Connecting Personal Narratives
Parallel Journeys
Both Jonathan’s quest to reconnect with Leif and Anna’s experience creating Pen15 highlight the profound impact of adolescent experiences on adult life. They explore themes of memory, self-acceptance, and the complexities of revisiting formative years.
Conclusion
This episode of Heavyweight masterfully intertwines Jonathan Goldstein’s personal journey to find closure with a beloved childhood crush and Anna Konkle’s creative process behind Pen15. Through heartfelt storytelling and candid conversations, the episode underscores the enduring influence of our past on present identities and relationships.
Notable Quotes
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Jonathan Goldstein: "For those who don't know the show, it is made by Anna Konkle and Maya Erskine, who are two real life best friends, and they play versions of themselves at 13." (01:12)
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Lucia Holt: "He had this, like, light blonde hair that he dyed and was not like a long, like, down to your butt hair, long, like, like a bob length." (05:02)
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Leif: "Do you know? So I literally was just new and different. I honestly think it was that simple." (37:16)
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Karina: "I adored you. I remember you being very intelligent. You were very funny." (40:33)
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Anna Konkle: "I was, like, trying to, like, manage nurses and all these other things and be there as much as I possibly could." (48:14)
This detailed summary captures the essence of the episode, highlighting the emotional depth and key discussions between the participants, supported by relevant quotes and timestamps for reference.