Therapuss with Jake Shane: Session 87 – Will & Cassidy

Release Date: August 11, 2025

Introduction

In Session 87 of Therapuss with Jake Shane, host Jake Shane welcomes his long-time friends and frequent podcast collaborators, Will and Cassidy, for what promises to be a candid and humorous deep-dive therapy session. Despite Jake's admission of recording the episode while severely hungover, the trio embarks on an insightful yet lighthearted conversation addressing personal dynamics, past experiences, and the complexities of their friendships.

Setting the Scene

The episode begins with Jake revealing his dire state, humorously setting expectations for the episode's erratic flow:

Jake [00:40]: "I have never been more hungover while filming an episode of Therapist in my entire life."

Cassidy and Will express their nervousness about the session, hinting at underlying tensions from a recent night out.

Cassidy [01:34]: "What do we have to talk about?"

Will [01:33]: "Are you nervous?"

Unpacking Last Night

A significant portion of the episode revolves around the trio recounting a tumultuous night that left residual stress and misunderstandings. The conversation oscillates between playful banter and sincere reflections on their interactions.

Conflict and Resolution

The discussion reveals that Will had a falling out with Jake the previous night, primarily stemming from feelings of insecurity and miscommunication while under the influence:

Will [08:04]: "I was feeling insecure. Insecure."

Jake [16:09]: "I have never felt this way."

Despite the initial conflict, the friends work through their emotions, showcasing the strength and resilience of their bond.

Friendship Dynamics and Relationships

Cassidy takes on the role of the matchmaker, highlighting the evolving relationship between Jake and Will. Their camaraderie suggests deeper feelings that are both acknowledged and playfully dismissed within the group.

Jake [10:20]: "Do you get jealous about that?"

Will [10:21]: "No."

The conversation underscores the importance of open communication and vulnerability in maintaining their friendships, even amidst moments of tension.

Personal Anecdotes and Shared Experiences

The trio reminisces about past trips to Miami and Boston, sharing humorous and heartfelt stories that illustrate the depth of their shared history.

Miami Memories

Their recounting of the Miami trip is filled with laughter and mishaps, such as losing Cassidy's passport:

Will [47:07]: "I was trying to set you up, though. I appreciate it."

Cassidy [46:54]: "I had to live in the moment for sure."

Boston Adventures

Their Boston trip is described as magical, though not without its challenges, emphasizing the unpredictable nature of their outings.

Will [48:27]: "I think it's fine to talk about trauma dumping on someone you’re meeting."

These stories not only provide entertainment but also serve as a backdrop for discussing broader themes like trust, support, and the impact of shared experiences on their relationships.

Therapy and Emotional Health

The session delves into the importance of therapy and emotional intelligence, with all three acknowledging their own struggles and the benefits they've reaped from seeking professional help.

Will [29:32]: "I go to therapy. But, Jake, I honestly felt like you."

Cassidy [34:08]: "I live with anxiety."

The candid discussion about mental health destigmatizes seeking help and reinforces the group's commitment to supporting each other.

Humor and Playfulness Amidst Tension

Throughout the episode, humor acts as a coping mechanism, allowing the friends to navigate their anxieties and insecurities with laughter and lightheartedness.

Jake [31:06]: "I'll serenade you any day, so do it now."

Will [58:02]: "This is too much for me."

These moments of levity provide balance, demonstrating how humor can alleviate tension and strengthen friendships.

Key Quotes and Highlights

• Jake on Sensitivity:

  Jake [56:11]: "But why do you say that? Why is it scary?"

• Will on Trauma Dumping:

  Will [34:07]: "I feel like I definitely trauma dump a little bit."

• Cassidy on Friendship:

  Cassidy [36:14]: "You're my first gay friend."

• Jake on Therapy:

  Jake [35:06]: "You should sleep here. I think you should move your flight."

• Will on Emotional Support:

  Will [55:34]: "We're talking about sensitivity."

Conclusion

Session 87 of Therapuss with Jake Shane encapsulates the essence of the show: blending humor with heartfelt introspection. Jake, Will, and Cassidy navigate their personal and collective challenges with a blend of vulnerability and wit, reaffirming their enduring friendship. The episode underscores the importance of open communication, mutual support, and the ability to find joy even in the aftermath of a chaotic night.

As the session wraps up with plans to order dinner and reflections on their shared history, listeners are left with a profound appreciation for the depth and resilience of genuine friendships.

Notable Moments:

• Hangover Humor: Jake’s admission of filming while hungover sets a humorous yet honest tone.
• Conflict Resolution: Addressing Will’s insecurity and the fallout from last night reinforces their strong bond.
• Shared Memories: Recounting trips to Miami and Boston provides context to their friendship history.
• Therapy Talks: Open discussions about mental health destigmatize seeking help.
• Playful Banter: Lighthearted jokes and teasing maintain an engaging and relatable atmosphere.

Quote Highlights:

• Jake on Friendship Importance:

  Jake [51:16]: "Do you think you'll be friends forever?"

• Will on Sensitivity:

  Will [55:07]: "We, us three, collectively, are very sensitive people."

• Cassidy on Anxiety:

  Cassidy [38:30]: "How do I change this?"

Timestamped Insights:

• 00:40 - Introduction and host's humorous hangover revelation.
• 08:04 - Will opens up about feeling insecure.
• 16:09 - Jake expresses unprecedented feelings of discomfort.
• 34:08 - Cassidy discusses living with anxiety.
• 56:11 - Conversation on sensitivity and its implications.

Final Thoughts

Therapuss with Jake Shane continues to excel in creating an intimate space for open dialogue among friends. Session 87 not only entertains but also offers valuable insights into managing personal relationships, the significance of vulnerability, and the healing power of humor. Whether you're a long-time follower or a new listener, this episode promises a heartfelt and relatable experience that underscores the universal journey of friendship and self-discovery.