Podcrushed: Valentine’s Day Special (100th Episode) Summary

Released on February 12, 2025, the 100th episode of Podcrushed celebrates Valentine’s Day with a nostalgic look back at some of the most memorable first crushes and heartbreaks shared by guests over the years. Hosted by Penn Badgley, Nava Kavelin, and Sophie Ansari, this special episode delves into the tumultuous emotions of teenage love, offering listeners a heartfelt and often humorous journey through middle school romance.

Introduction

Penn Badgley opens the episode with a mix of excitement and vulnerability, stating, “Right, Should I be saying the full word? Valentine's Day today we have a compilation... a special episode where we have some of our favorite first crush and first heartbreak stories from guests over the years.” (00:02) He then hands over the microphone to Sophie Ansari, who guides listeners through the compilation of heartfelt tales.

Crush Stories

IO Debris: The Early Days of Adoration

IO Debris shares her first significant crush on her friend Bill, recounting how it began in fifth grade when Bill “origamied me a heart out of a dollar” (02:15). She humorously reflects on her teenage certainty, “I thought he was the best... I was gonna be Vietnamese now. Like, this is, like, mine. This is, like, my husband.” (04:30) Despite her deep feelings, IO admits, “nothing happened, but he was, like, my first big crush,” highlighting the innocence and intensity of young love.

Jenna Ortega: Navigating Awkward Affections

Jenna Ortega recounts her experiences with crushes during middle school, including a memorable encounter where she felt physically ill around a boy she liked. She describes the overwhelming emotions: “I’m like, oh, my God. He held my hair back. I must be in love with him.” (25:45) Jenna’s story emphasizes the physical and emotional challenges of expressing affection at a young age.

Julia Louis-Dreyfus: First Touch and Unintended Kisses

Julia Louis-Dreyfus reminisces about her first experience touching a boy’s shoulder in a fifth-grade dance class. She recalls her realization, “he feels like a regular shoulder... he’s another person. Just like me.” (34:20) Additionally, Julia shares a humorous incident where a spontaneous kiss from a classmate left her astonished: “He didn’t know. I didn’t even respond.” (36:05) Her stories capture the confusion and excitement of early romantic gestures.

Rainn Wilson: From Crushes to Friendships

Rainn Wilson talks about his early crushes on girls he considered "cute" and how these feelings evolved over time. He shares a poignant moment when a crush turned into a lasting friendship: “Tria and I are now, like, best friends. We just know each other really, really deeply.” (42:50) Rainn’s narrative highlights the enduring bonds that can form from youthful infatuations.

Z Way: Lessons in Boundaries and Self-Respect

Z Way reflects on his first crush and subsequent heartbreak in high school. He details how confessing his feelings led to an important lesson on boundaries: “It was just me getting a lesson on boundaries.” (58:10) Z’s story underscores the importance of self-respect and understanding personal boundaries in romantic relationships.

Matthew McConaughey: Overwhelming Affection

Matthew McConaughey shares his intense feelings during his first love, detailing how overzealous expressions of affection led to a painful breakup: “The gifts were too much. She broke up with me right after I’d given all these gifts.” (62:30) His experience illustrates how overwhelming emotions can sometimes lead to unintended consequences in young relationships.

Seth and Josh Meyers: Different Paths of Heartbreak

Seth Meyers discusses his lack of profound heartbreaks, attributing it to superficial relationships during his youth: “I never had a girlfriend that I was capable of being heartbroken about.” (77:15) In contrast, his brother Josh Meyers recounts a deeply emotional breakup that led him to a moment of personal crisis: “I went and I saw our old house... I was beside. I was like, she, you know, it’s over.” (80:45) Their contrasting stories offer a glimpse into how different individuals process young love and loss.

Heartbreak Stories

IO Debris: The Pain of Unreciprocated Feelings

IO reflects on her heartbreak after her first crush didn’t pan out, revealing her adolescent strategies to cope, such as “listening to Muse” and immersing herself in secular music (07:50). She humorously admits, “How am I gonna change myself? And it's like, okay, the answer is right in front of you. Please just take it in.” (10:10)

Jenna Ortega: Overcoming Embarrassing Moments

Jenna shares a cringe-worthy experience where she vomited during a conversation with her crush, leading to embarrassment and lessons in resilience. She describes the aftermath: “My teacher had me walk all the way to the principal's office... So I was so embarrassed...” (22:30) This story highlights the vulnerabilities and lessons learned from teenage crushes.

Julia Louis-Dreyfus: Emotional Growth Through Heartbreak

Julia discusses her first heartbreak when her boyfriend dumped her after she was too affectionate: “She broke up with me right after I’d given all these gifts.” (35:50) She reflects on the emotional turmoil and eventual personal growth, emphasizing the importance of sitting in pain and building self-confidence.

Rainn Wilson: Moving Beyond High School Heartbreak

Rainn recounts his heartbreak with Tria, a girl who eventually became his best friend. He shares the emotional impact of being dumped: “I poured so much into this crush that had no interest for me...” (43:30) His narrative underscores the enduring impact of teenage heartbreak and the value of lasting friendships.

Z Way: Navigating Rejection and Self-Worth

Z elaborates on his high school breakup, where he faced rejection that taught him vital lessons about self-worth and the complexities of young love: “That taught me the lessons of men being sometimes deeply, deeply annoying.” (59:40) His story emphasizes personal growth through painful experiences.

Matthew McConaughey: The Aftermath of Overwhelming Affection

Matthew details how his excessive gift-giving led to a sudden breakup, leaving him feeling crushed and confused about love: “We were crying and having sleepless nights... and to hear that and then eventually get to remember, you're a catch.” (63:20) His experience illustrates the delicate balance of affection in relationships.

Seth and Josh Meyers: Different Experiences with Breakups

While Seth remains relatively unaffected by past relationships, Josh describes a profound emotional crisis following a breakup that involved losing his car and confronting his parents about his actions: “He was in Okemons, Michigan... He was very depressed and going to a place called Bagel Fragile.” (81:00) This stark contrast between the brothers highlights varied emotional responses to heartbreak.

Conclusion

The episode wraps up with nostalgic reflections from Evam Rachel Wood, who humorously shares her first crush on Penn Badgley, bringing the conversation full circle to the podcast’s origins. As the hosts close the episode, they emphasize the universal and timeless nature of teenage emotions: “It's such a big middle school... Just so, like, you're just looking for someone.” (99:30)

Podcrushed effectively captures the rollercoaster of middle school romance, blending humor, vulnerability, and relatable anecdotes to celebrate the complexities of young love. This milestone episode serves both as a tribute to the past and a comforting reminder that the feelings of heartache and joy are shared by many.

Notable Quotes with Timestamps:

• IO Debris: “He origamied me a heart out of a dollar.” (02:15)
• Jenna Ortega: “I put my finger up, and my mouth started to fill with a certain kind of thick fluid.” (25:45)
• Julia Louis-Dreyfus: “He feels like a regular shoulder… he’s another person. Just like me.” (34:20)
• Rainn Wilson: “Tria and I are now, like, best friends.” (42:50)
• Z Way: “It was just me getting a lesson on boundaries.” (58:10)
• Matthew McConaughey: “She broke up with me right after I’d given all these gifts.” (62:30)
• Seth Meyers: “I never had a girlfriend that I was capable of being heartbroken about.” (77:15)
• Josh Meyers: “Bagel Fragile is really funny.” (80:45)

Hosts:

• Penn Badgley
• Nava Kavelin
• Sophie Ansari

Special Guests:

• IO Debris
• Jenna Ortega
• Julia Louis-Dreyfus
• Rainn Wilson
• Z Way
• Matthew McConaughey
• Seth Meyers
• Josh Meyers
• Evan Rachel Wood

Production:

• Senior Producer: David Ansari
• Editing: Clips Agency
• Sales and Distribution: Lemonada Media

Podcrushed continues to resonate with listeners by sharing authentic and relatable stories from the treacherous yet transformative years of middle school, making the 100th episode a heartfelt celebration of love’s early chapters.