The Wayback with Ryan Sickler — Episode 96: Kerryn Feehan - Field Trip Flashing

Date: October 30, 2025
Guest: Kerryn Feehan
Host: Ryan Sickler

Episode Overview

This episode of The Wayback takes a hilariously nostalgic trip through the childhood and teenage years of comedian Kerryn Feehan. With characteristic candidness and wicked humor, Feehan and Sickler reminisce about growing up in small-town Massachusetts, navigating awkward rites of passage, family dynamics, and the mischief that marked their coming-of-age. The conversation is lively and unfiltered, weaving together themes of sibling antics, Catholic school strictness, adolescent experimentation, formative embarrassments, and the universal yearning to fit in and be noticed.

Key Discussion Points & Insights

1. Growing Up in Marshfield (M. Vegas), Massachusetts

• Kerryn’s Background:

  • Grew up in Marshfield, MA (“M. Vegas”) but attended Sacred Heart instead of the local high school [06:11].
  • Describes her childhood neighborhood as safe and quaint, filled with classic New England touches like ponds and marshes [06:41].

• Nostalgia and Firsts:

  • Kerryn’s humorous account of her first sexual experiences, including being “fingered” behind her house by a boy who earned it with a long marsh walk:

    “Let him finger me, dude. So romantic, though. He walked me around a whole marsh. Like, this guy’s in love with me.”
    (Kerryn, 07:04)

2. Childhood Memories & Family Dynamics

• Sibling Relationships:
  • Middle child with an older brother and younger sister—feels it made her “desperate for attention.” [17:37]
  • Recalls losing her brother during a Myrtle Beach family vacation and the family’s ensuing panic—a universal childhood terror [17:33].
• Mother-Daughter Bond:
  • Close relationship with her mom, who was “a riot” and remains so; they still talk every day [38:04].
  • Kerryn praises her mother's natural beauty and humor, reminiscing over old family photos [37:07].

3. School Life: Catholic School Discipline and Carpool Chaos

• Carpool Fights and School Stories:
  • Vivid tales from carpooling to private/Catholic school, including an epic hair-pulling fight in the station wagon’s wayback seat [04:06].
  • The dynamic range of “mom drivers,” moods, and parental attitudes in small-town carpools [05:03].
• Getting in Trouble:
  • Chronic trouble at school—detentions for writing “dirty notes to boys,” inappropriate jokes, and general rowdiness [24:25].
  • Catholic guilt and authority:

    “When a nun reads something, like a 12-year-old... it’s a... Like when a nun reads something. Like, you... it’s like, just shame you.”
    (Kerryn, 26:48)

  • Had to serve detentions, sometimes involving humiliating solitary walks around the playground [27:13].

4. Awkward Adolescence: Field Trips and Flashing Stories

• Most Notorious Antic:
  • The story behind the episode title: During a school field trip to an amusement park, Kerryn and her friend, under peer pressure, flashed their classmates while riding the “dragon swing” ride [14:44].

    “You flash the boys... your friend Hillary with, like, huge tits... she starts it and she’s like, do it too. And I’m like, why? I don’t want to. And she’s like, just do it. I was like, all right. I love peer pressure.”
    (Kerryn, 14:44)

  • The resulting rumor mill and the enduring legacy of such schoolyard legends [15:10].
• Earlier Experiments:
  • Recounts an elementary school “show me yours, I’ll show you mine” episode that left her feeling duped and exposed [12:17].

5. Teen Rebellion, Parties, and Underage Hijinks

• Small-Town Teen Culture:
  • Parties often happened in trucks deep in the woods—“just get in a truck and drive deep into the woods and, like, do whatever we were gonna do” [29:34].
  • Early drinking at 14, sneaking out, getting sick from mixing random liquors—mortified but sociable memories [30:01].
• Encounters with the Law:
  • Got busted for senior skip day drinking on a private beach (not arrested, just a warning) [28:35].
  • Later, avoided arrest when police caught her group smoking weed in New York because the officer didn’t see her doing it:

    “I didn’t see you smoking. And I was like, I guess I wasn’t smoking then. And I abandoned my friends.”
    (Kerryn, 29:00)

6. Family Vacations and Sibling Antics

• Memorable Trips:
  • Family flew to Disney World after her mother’s car accident settlement—mother determined despite a neck brace [16:10].
  • Endured long road trips to Myrtle Beach, including classic “peed my pants from laughter” moments [16:30].
• Siblings Getting Lost:
  • Both Ryan and Kerryn share stories of losing their brothers at large beaches—a common childhood panic [18:17].

7. Dance, Ballet, and Brushed Dreams

• Ballet Ambitions:
  • Danced for the Boston Ballet as a child, performing in The Nutcracker—a prestigious but grueling experience [08:04].
  • Ultimately told she’d never be a star (“you’ll be in the chorus”), reflecting on the early harshness of competitive arts [33:13].
  • Maintains a sense of humor about her dashed ballet dreams:

    “When did the ballet career stop? — When the heroin began.” (joking, 30:52)

8. Sexual Awakening and Girlhood in Catholic School

• Curiosity and Provocation:
  • Kerryn candid about being an “early bloomer” in expressiveness and sexual curiosity:

    “Why are you such a horny young lady pulling your boobs out...?”
    (Ryan, 25:00)

  • Examines the effect of nuns, repression, and all-girls-acting school culture [27:02].
• Mischief as Middle Child:
  • Naturally took the lead—organizing, giving others “jobs,” bossy from the beginning [26:02].

Notable Quotes & Memorable Moments

• “He walked me around a whole marsh. Like, this guy’s in love with me.” (Kerryn, 07:04)

• “He earned that finger bang. I’m telling you.” (Kerryn, 11:57)

• On field trip flashing:

  “And then everybody talked about… You won’t believe what Hillary did. She flashed her boobs. And Karen tried to flash whatever she’s been. She’s growing whatever.”
  (Kerryn, 15:10)

• On early sexual curiosity:

  “But like in kindergarten, I made a bet with this kid Toby. Like, show me yours, I’ll show you mine in kindergarten. Maybe first grade.”
  (Kerryn, 12:17)

• Reflections on strict Catholic schooling:

  “When a nun reads something… just shame you.”
  (Kerryn, 26:48)

• On ballet and rejection:

  “They just straight up like, yeah, it ain’t gonna happen for you. Which is kind of like merciful in some ways, in other ways heartbreaking.”
  (Kerryn, 33:13)

• On being a middle child:

  “That’s why I’m so desperate for attention. But don’t feel the need to procreate because, like, growing up, I was like, There’s enough people.”
  (Kerryn, 17:37)

Important Segment Timestamps

• Kerryn’s childhood home & first romance: 06:41–07:07
• Ballet, Boston Ballet & Nutcracker stories: 07:43–09:13
• Adolescent experiments in nudity: 12:06–12:53
• Field trip “flashing” story: 14:44–15:14
• Family vacation, brother gets lost: 17:33–18:24
• Trouble with nuns & detention stories: 24:25–27:13
• Senior skip day & weed arrest tale: 28:13–29:11
• Teen parties in trucks, growing pains: 29:34–30:49
• Why ballet ended & reflections on resiliency: 32:52–34:48
• Moments of sibling mischief (bringing sister home drunk): 35:26–36:17

Episode Tone & Style

Friendly, confessional, and unvarnished, the episode crackles with Feehan’s sharp, self-deprecating wit and Sickler’s nostalgic, good-natured curiosity. The conversation is peppered with quick-fire jokes, edgy reminiscences, and effusive affection for the weirdness and wildness of growing up. Both host and guest revel in the joy (and mortification) of shared 80s and 90s formative experiences.

Guest’s Upcoming Projects and Plugs

• Stand-up special: “Don’t Serve Me” available on YouTube [39:03]
• Podcast: Only Fiance
• Live dates:
  • November 7: The Hideout, Boston
  • November 8: Co-headlining show at the New York Comedy Festival

Subscribe to her YouTube and follow her on social media for clips and updates.

This episode serves as both a hilarious and relatable window into the universal—and uniquely Kerryn—growing pains and misadventures of youth, underscored by sharp humor and heartfelt reminiscence.