The Breakfast Club: "Carefully Reckless: My Past vs. My Future"
Release Date: June 9, 2025

Introduction

In this compelling episode of The Breakfast Club, titled "Carefully Reckless: My Past vs. My Future," host Michael Kasson engages in an intimate and candid conversation with comedian and actress Jess Hilarious, alongside guest Taylor. The discussion delves deep into the complexities of past relationships, personal growth, and the challenges of moving forward while dealing with unresolved feelings.

Jess Hilarious Shares Her Personal Journey

The episode kicks off with Jess Hilarious recounting her tumultuous relationship with her first boyfriend, a childhood friend who was deeply entrenched in the drug trade.

Jess Hilarious [02:30]: "One of my childhood friends was my very first boyfriend in life. He was the big-time drug dealer in our city. We've been together on and off for about 15 years."

Jess paints a vivid picture of her life intertwined with crime and the constant threats that came with dating someone involved in dangerous activities.

Jess Hilarious [03:20]: "During the time of our relationship, he was back and forth to prison, involved in shootouts, all the things that would make a girl want out."

Despite the chaos, Jess reflects on the longevity of their relationship, emphasizing that her relationship remained tumultuous but free from infidelity.

Jess Hilarious [05:00]: "He never cheated, as far as I know. But being the girlfriend of a drug dealer became very old and tired for me as I got older. So I gave him an ultimatum. Me or that life."

Confronting the Past and Embracing the Future

Jess made a definitive choice to leave the perilous lifestyle behind, setting the stage for a healthier relationship with a new partner. However, three years later, her ex-boyfriend resurfaces, presenting a dilemma between past attachments and present commitments.

Jess Hilarious [06:00]: "A few months ago, my ex pops up out of nowhere at my job. I thought he was coming to rob it. What the fuck?"

Taylor and Michael Kasson offer their perspectives, highlighting the internal conflict Jess faces.

Taylor [07:20]: "I think just don't jump out there and just, like, go, you know, just because he came to you."

The conversation intensifies as Jess grapples with the resurgence of feelings for her ex amidst her engagement to her current fiancé.

Jess Hilarious [14:30]: "He tried to be legit and everything. And she said, wow. Crazy thing is, I felt so good talking to him. All the memories flushed. I was back in love."

Navigating Emotional Turmoil and Making Tough Decisions

The hosts delve into the emotional turmoil Jess experiences, questioning whether her feelings are rooted in genuine love or residual attachments from a turbulent past.

Michael Kasson [08:07]: "And everything that glitters is not gold."

Taylor [20:18]: "Stop holding onto the what if."

Jess's current fiancé, described as everything she once desired, stands in stark contrast to her tumultuous past, prompting a deep discussion on loyalty, personal growth, and the fear of repeating past mistakes.

Michael Kasson [16:01]: "You've known him since he was younger. He knows what to say to get back in your good graces."

Jess Hilarious [30:53]: "I don't regret it though for like four years. Like you still... What are you holding on to, sir?"

Key Insights and Discussions

Throughout the episode, several key themes emerge:

1. The Impact of Past Relationships: Jess's long-term relationship with a drug dealer illustrates how past experiences can shape present decisions and emotional states.

2. Fear of Relapse into Old Habits: The discussion underscores the fear that individuals might inadvertently fall back into detrimental patterns when confronted with unresolved pasts.

3. Importance of Self-Reflection: Jess's journey emphasizes the need for introspection and understanding one's true feelings before making life-altering decisions.

4. Support Systems: The role of friends like Taylor and host Michael Kasson proves invaluable in navigating complex emotional landscapes.

Taylor [20:20]: "Girl, fuck that, then."

5. The Complexity of Love and Loyalty: The episode sheds light on how love isn't always straightforward and can be entangled with loyalty, fear, and personal history.

Conclusions

In "Carefully Reckless: My Past vs. My Future," Jess Hilarious opens up about the intricate dance between her past and present relationships. The episode serves as a poignant reminder of the enduring impact of past choices and the courage required to forge a path toward a healthier, more secure future.

Listeners are left contemplating the delicate balance between honoring one's past and embracing the promise of the future, all while navigating the complexities of love, loyalty, and personal growth.

Jess Hilarious [32:25]: "Girl, fuck that, then."

Notable Quotes:

• Jess Hilarious [02:30]: "One of my childhood friends was my very first boyfriend in life. He was the big-time drug dealer in our city."

• Michael Kasson [08:07]: "And everything that glitters is not gold."

• Taylor [20:20]: "Stop holding onto the what if."

• Jess Hilarious [32:25]: "Girl, fuck that, then."

Final Thoughts

"Carefully Reckless: My Past vs. My Future" offers an unfiltered look into the struggles of breaking free from a dangerous past while striving for a better future. Through Jess Hilarious's heartfelt revelations and the supportive dialogue with Taylor and Michael Kasson, listeners gain valuable insights into overcoming personal demons and making empowering life choices.

Listen to more episodes of The Breakfast Club on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.