Podcast Summary: Therapuss with Jake Shane
Episode: Session 95 – Dylan O’Brien
Date: September 18, 2025
Guest: Dylan O’Brien
Host: Jake Shane
Overview of the Episode
In this engaging and often hilarious “therapy session,” host Jake Shane welcomes Dylan O’Brien for a conversation that artfully explores both the light and deep sides of life, relationships, mental health, and career. From reminiscing about Teen Wolf and discussing the themes in Dylan’s new film "Twinless," to swapping stories about Jersey Shore, mental health struggles, and the quirks of being a millennial, the episode blends introspection, banter, and practical advice—true to the signature Therapuss tone.
Key Discussion Points & Insights
1. Astrology, Millennials, and Icebreakers
- Jake opens by guessing Dylan’s star sign, leading into a playful discussion about astrology and how generational identity shapes self-perception.
- Memorable moment:
- [02:25] Dylan: “Oh yeah, babe, I know [my star chart]…”
- [08:16] Dylan: “I guess I feel insecure about being a millennial.”
- Jake reassures Dylan about millennial identity. [08:28]: “I think I’ll feel that way one day about being Gen Z. But that time hasn’t come yet.”
2. Planes, Edibles, and Anxieties
- Discussion of travel rituals, with both talking about taking edibles on flights, and how weed can both soothe and spark anxiety.
- [03:43] Dylan: “Are we ever fine the first 15 minutes after we… [smoke]? Like, why do we choose that?”
- They riff on the creativity and food enjoyment that comes with being high, but also the initial anxiety.
3. Pets, Normal Life, and Social Media
- Dylan shares about his dog, Tony (“Rigatoni” with a Y), and why he dislikes the “COVID dog” label—insisting he was intentional about pet ownership. [10:26]: “When I got my dog, things were already open back up. I was very, like, intentional about that because of socializing the dog.”
- Both discuss enjoying "normal life" outside the entertainment bubble.
4. Teen Wolf and Early Acting Journeys
- Dylan relives his Teen Wolf memories, maintaining a sentimental attachment to the T-shirt he wore in the pilot ([14:18] “It’s just a touch of sentimentality and...it’s like a one little keepsake from the show”), and revisits the plot and impact of the series.
- Dylan opens up about stumbling into acting via YouTube sketches as “Movie Kid,” his lack of formal training, and the role of accidental virality.
- [23:15] “Honey, I don’t know if I’ve ever talked about this...I was coaching a Little League baseball team...”
- Jake gets Dylan to reflect on how loneliness as a kid made him creative.
- [26:27] Dylan: “I seriously think about that a lot. Even with so much with Twinless coming out. We’ve been talking so much about kind of themes of loneliness and...how informative that can be.”
5. "Twinless" – Themes & Reception
- Jake explains why audiences, particularly young gay people and anyone who’s experienced grief, should see the film.
- The duo unpacks the importance of forgiveness and empathy for the flawed protagonist.
- [28:04] Dylan: “It’s a good barometer...of your kind of relationship to forgiveness.”
- Dylan shares the difficulty of getting "Twinless" made, how people found the character “irreedeemable,” and why he’s proud of its empathetic storytelling ([29:11] “It’s been a journey with this film...a large part...was because people deemed that character to be completely irredeemable…”).
- Jake confesses having to pause the movie from stress, especially the art museum and double date scenes ([30:32] – “There was moments where I had to pause it...I was so stressed out.”).
6. Being Yourself, Reality TV, and East Coast Upbringing
- They swap stories about loving Jersey Shore, directness, and how “being yourself” (à la Snooki or Lena Dunham) is admirable and rare.
- Directness as kindness:
- [45:44] Dylan: “Directness, to me, is kindness, in a way that I don’t think people receive that the same way...I much prefer a person who might be perceived as aggressive, but tell you straight to your face.”
- Both reflect on growing up on the East Coast and its “tell it like it is” culture.
7. Mental Health: OCD, ADHD & Therapy
- Jake and Dylan discuss their experiences with ADHD and OCD, the stigma around medication, and how compulsions can shape daily life.
- [52:48] Jake details OCD rituals: “I used to...add a song to a playlist...four times...when I would watch...Netflix, sometimes I’d have to watch a scene four times...”
- Touch on therapy, its value, and the challenges of “doing therapy right” ([64:01] “No, I think it’s normal to not feel that yourself”).
8. Hollywood Real Talk: Acting, Fame & Control
- Dylan is candid about his “normal” lifestyle between projects and his aversion to set visits when not working ([37:01] “I really don’t like being on sets when I’m not working. Why?”).
- On not being a “control freak” but disliking when people assume they know him based on press or online snippets.
- [77:26] “I hate people just sort of deciding that they know who I am...I’m very sensitive about my character.”
9. Advice Columns: “Tell Me What’s Wrong” Write-ins
- Classic "Therapuss" segment where audience dilemmas are addressed with candor:
- Roommate drinks too much but is fun (solution: early 20s, they’ll figure it out – [61:54]).
- Rekindled high-school romance with old bad habits (solution: “sounds like it would be good for them to break up” – [65:15])
- Wanting to act but lacking experience: Just try, make little things with friends, but Dylan cautions, “I wouldn’t encourage anyone to pursue acting...I got really, really lucky.” [71:00]
- Boyfriend runs from mountain lion, leaves girlfriend: (“You can’t hold someone hostage over an instinct in a moment of panic and make it about you” – [73:09])
10. Reflections on Aging, Growth, and Comfort
- Dylan expresses comfort with his 30s and says he wouldn’t want to go back to his 20s ([86:36]).
- Both observe how meaningful conversation is more fulfilling than big social noise as they grow up.
Notable Quotes & Memorable Moments
-
Dylan O’Brien on millennial insecurity:
- [08:16] “I guess I feel insecure about being a millennial.”
-
On loneliness and creativity:
- [26:27] “If you’ve experienced periods of [loneliness] in your childhood, how informative that can be. And so I think that’s so much of what brought me to that project.”
-
On acting and authenticity:
- [35:23] “The only way I could even do it is by, like, going off of things that I know are real, things that feel authentic…”
-
On directness as kindness:
- [45:44] “Directness, to me, is kindness in a way that I don’t think people receive that the same way...I much prefer a person who might be perceived as, like, aggressive...but tell you straight to your face.”
-
On OCD compulsions:
- [52:48] Jake: “When I would add a song to a playlist, I would have to add it four times.”
-
On being “sensitive” and defensive of character:
- [77:37] Dylan: “I hate people just sort of deciding that they know who I am, I guess, you know...I’m very sensitive about my character.”
-
Advice to young actors:
- [67:09] “Give it a shot...because it’s a crap shoot anyway. Even if you were, you know, currently in school...the things you can control at least are like, if you want to be doing that, then, like, do it. Go to LA. Find people who also want to be doing it.”
Important Timestamps
- Star Signs & Icebreakers: [02:03 – 05:34]
- Flying high/anxiety/weed: [02:49 – 04:05]
- Millennial Identity: [08:09 – 08:28]
- Dog stories & Tony the Rigatoni: [09:50 – 11:06]
- Teen Wolf Memories: [14:45 – 16:11]
- Transition to Acting/YouTube beginnings: [23:15 – 27:27]
- Twinless, empathy & forgiveness: [27:29 – 29:38]
- On Directness & East Coast culture: [45:44 – 47:03]
- OCD, ADHD & Mental Health: [52:48 – 53:59]
- Audience Dilemmas: [61:30 – 73:49]
- Discussion on control and fame: [77:02 – 80:28]
- Reflections on aging, social comfort: [86:31 – 87:44]
Tone & Language
The episode is conversational and irreverent, mixing witty banter (“I guess I do have range. Wow” – Jake [34:00]) with honest confessionals and moments of genuine vulnerability. Both host and guest show a knack for self-deprecation, warmth, and quick adaptation to emotional honesty—even within the chaos of their tangents and inside jokes.
Final Takeaways
- Vulnerability & Realness: Dylan and Jake model open discussion of insecurity, mental health, and change, shattering the myth that public personas are always polished or static.
- Creativity from Loneliness: Early isolation bred unexpected creativity in Dylan, leading him from “Movie Kid” on YouTube to acclaimed acting roles.
- Advice: Empathy and forgiveness are crucial—both in movies, life, and relationships. And sometimes, you just need to let go of the mountain lion moment.
- Career: There’s no formula in Hollywood; luck, timing, and self-made work all matter.
- Aging: Embracing each stage, with honesty about its challenges. Greater value is found in authentic one-on-one connections than the background noise of a big crowd.
Closing Moments:
Dylan: “You’re way more mentally sound than you think you are.” [88:36]
Jake: “Thank you so much.”
Dylan: “That’s so great. Or at least if you’re in your own hot mess-ness, I feel like you handle it really well.” [88:51]
End: They agree to meet up in New York, expressing real enjoyment and camaraderie.
Jake: “Thank you for coming on, Therapuss.”
Dylan: “Thanks for having me anytime. And I had a terrible morning.”
Jake: “I could never tell. It’s true.”
For Listeners Who Missed the Episode
This episode is perfect for fans of conversational podcasts that mix humor with substance, especially if you appreciate inside-Hollywood stories, deep dives into creative journeys, honest talk about mental health, and unfiltered friendship chemistry. You’ll leave with some practical advice and a smile—whether you’re dealing with a roommate who parties too much, aspiring to act, or just figuring out your 20s and 30s.