RISK! Podcast – "Unrequited" (February 10, 2026)

Episode Overview

In the "Unrequited" episode of RISK!, host Kevin Allison curates three deeply personal and raw stories exploring the sting, messiness, and surprising lessons of unreturned affection and sexual awakening. Told with the show’s signature blend of unfiltered candor and bittersweet humor, the episode features first-time and returning storytellers sharing moments of longing, rejection, heartbreak, and, ultimately, self-discovery. The stories span adolescent summer escapades, an exquisitely awkward college crush, and a closeted midshipman's journey toward self-acceptance at the Naval Academy.

Key Stories & Insights

1. Connor O'Donoghue: "I Was the Appetizer"

[03:46–15:27]

• Setting: The story opens in a psychiatric hospital in Ireland, summer 2002, where Connor, dealing with depression, seeks belonging among the teen patients.
• Experiences of Isolation and Longing: Connor recounts the loneliness of summer camps as a fat, gay teen and how, at the hospital, he finally found his own "summer camp tribe."
• Forming Intimate Bonds: The young adult group engages in both innocent and charged activities—music, confidences, playful sexual experimentation—forming a cocoon of acceptance and wildness.
• Unrequited Love:
  • Connor develops a crush on David, a straight boy, who nonetheless allows a certain intimacy:

  "He knew I was in love with him. He allowed me to be in love with him." — Connor O'Donoghue [05:51]

  • He relishes small tokens and moments—even David’s used underwear—without reciprocation.
• Climactic Birthday Encounter:
  • During David's 18th, the emotional triangle with Jojo (an 18-year-old friend) comes to a head.
  • Connor gives David a blowjob, but is left as a bystander when David's attention returns to Jojo.

  "My mouth was the appetizer. He wanted her vagina to be the main course. Of course I was sad, but not surprised." —Connor O'Donoghue [11:17]

  • The story descends into awkwardness and heartbreak, with Connor relegated to observer status.
• Impact and Reflection:
  • Though he doesn't get what he hoped, Connor feels “lucky to have even got that much”.
  • For years, he discounts his own desirability, internalizing that fat people weren't objects of desire.
  • Moving to London at 35, Connor discovers the world of chubby chasers, embrace, and finally self-acceptance:

  "...at the age of 44, I'm still very single, still living in hope that just maybe the next penis might actually be the one that sticks around." —Connor O'Donoghue [15:21]

Memorable Moments

• Connor’s detailed, vulnerable depiction of adolescent sexual curiosity and pain.
• A nuanced view of found family, and the way unrequited love shapes self-perception.

2. JC Cassis: "Casualties of a Crush"

[15:58–21:34]

• Setting: College, first co-ed, social environment after an all-girls schooling.
• The Crush: JC becomes enamored with Bobby, an impossibly sophisticated boy with a “romantic backstory.”
• The Confession:
  • Despite nerves, she resolves to tell him how she feels:

  "'I have something to tell you.' He was like, 'Yeah." And I was like, 'Well, I like you, and I think you're really cute…'" —JC Cassis [17:39]

  • Bobby's response, “Well, I know that, and I have known that. And unfortunately, I don't feel the same way.”
• Brutal Honesty:
  • As JC tries to lighten the mood with, "Let me know if you ever change your mind," Bobby responds, "I'm never going to change my mind," shutting down any hope.

  "'I'm never going to change my mind.' I’m just like, oh, my God. Like, dude, I just took a big risk telling you…" —JC Cassis [19:37]

• Lingering Impact:
  • The moment haunts JC over two decades later, teaching her about risks in vulnerability and the often unintended cruelty of honesty:

  "It's 22 years later, you guys, and I'm still fucking thinking about that moment." —JC Cassis [20:23]

  • Lessons learned: Don’t get crushes without really knowing someone, and vulnerability is both risky and illuminating.

Memorable Moments

• The relatable, mortifying humor of trying to salvage dignity after rejection.
• The “collateral damage” of formative embarrassment that outlasts academic learning.

3. J. Michael: "Ready for Asking"

[32:13–44:44]

• Setting: U.S. Naval Academy, early 2000s—the era of “Don’t Ask, Don’t Tell.”
• Describing the Closet:
  • J. Michael depicts extreme fear of discovery, isolation, and creative self-denial, including elaborate rituals to evade detection—sleeping on top of made beds, stashing banned items, etc.

  "I was both Catholic and closeted, and that's a real train you don't want to ride on." —J. Michael [34:20]

• Yearning for Connection:
  • Even browsing gay content online feels perilous, but longing drives him to the site XY.com—coded messaging, cryptic personal ads, and paralyzing fear.
• First Encounter:
  • During a hurricane-induced power outage, he dares to meet “Jeff” from XY. Their tryst is awkward and brief but momentous:

  "I ejaculated so quickly, I set a world record." —J. Michael [36:45]

• Liberation:
  • Jeff later invites J to DC, leading him—unknowingly—to his first gay bar.
  • The joy and shock of seeing “so many people there...like me,” culminates with shirtless dancing and a first passionate kiss on the dancefloor.

  “He kissed me in a way that was...he knew what he was doing. I fell in love… everything in my little brain exploded.” —J. Michael [41:36]

• Aftermath:
  • The romance fizzles immediately, but the heartbreak shifts from existential (“being punished by God”) to the mundane (“a Naval Academy junior fuckboy”).
  • J begins to allow himself to ask, if not fully tell, who he is.

  “…while I wasn't ready to do any of the telling, I definitely had started asking.” —J. Michael [44:08]

Memorable Moments

• A humorous, poignant retelling of navigating forbidden desire under oppressive rules.
• The electric sense of community found in a crowded queer bar for the first time.

Host Reflections: Kevin Allison

[22:12–26:39, 44:44–end]

• On Patterns & Openness:
  • Kevin notes that experiences of heartbreak or mishap often lead to “limiting stories” about love or sex:

  "I always hope that people...remain open to possibility, you know, because chemistry, timing, hormones..." [23:03]

  • He recommends holding onto hope, staying alert to red flags, but being open to “giving it another chance with this new fella.”
• Comparison with Stand-Up:
  • Tells a joke about comedians bombing and succeeding with the same material, reinforcing the message: don’t generalize from one heartbreak or failed attempt.
• Film Recommendation:
  • Praises queer director Jun Lee’s "Queer Panorama" for its nuanced take on intimacy found through random hookups, not just the usual narrative of soulless sex.

Notable Quotes & Timestamps

• "He knew I was in love with him. He allowed me to be in love with him."
  —Connor O’Donoghue [05:51]

• "My mouth was the appetizer. He wanted her vagina to be the main course."
  —Connor O’Donoghue [11:17]

• "'I'm never going to change my mind.'"
  —Bobby (quoted by JC Cassis) [19:37]

• "It's 22 years later, you guys, and I'm still fucking thinking about that moment."
  —JC Cassis [20:23]

• "I was both Catholic and closeted, and that's a real train you don't want to ride on."
  —J. Michael [34:20]

• "I ejaculated so quickly, I set a world record."
  —J. Michael [36:45]

• "He kissed me in a way that was...he knew what he was doing. I fell in love..."
  —J. Michael [41:36]

• “…while I wasn't ready to do any of the telling, I definitely had started asking.”
  —J. Michael [44:08]

Important Segment Timestamps

• Connor O’Donoghue’s Story (“I Was the Appetizer”): [03:46–15:27]
• JC Cassis’ Story (“Casualties of a Crush”): [15:58–21:34]
• J. Michael’s Story (“Ready for Asking”): [32:13–44:44]
• Kevin Allison’s Host Commentary: [22:12–26:39], [44:44–end]

Tone and Takeaways

• Language & Tone: Stories are told with raw honesty, wit, and self-deprecating humor—there’s vulnerability in each confession (“crush my soul... but I have a joke, you know?”), alongside moments of wry reflection and emotional wisdom.
• Themes: The pain of longing for love or acceptance that is never returned; the formative, sometimes humiliating, ways those moments linger; and the paths to self-acceptance and future readiness.
• Final Message: RISK! encourages listeners to “take a risk”—to remain open to possibility, even after heartbreak.

This summary captures the episode’s rich tapestry of emotional storytelling, preserves the speakers’ voices, and highlights the vulnerable, hilarious, and sometimes painful reality of unrequited love and longing.