Ready to get weird and wise? Jordan and J.T. play the first round of Uncomfortable On Purpose. Think Truth or Truth: the questions you’d rather not ask your partner but really should.

This round cuts deep. A provocative and revealing Q&A-style game that digs beneath the surface. Topics we usually tiptoe around—shame, addiction, fear, failure—but with the goal of healing, not harm. A darkly playful excavation of your emotional scar tissue—because healing can be sexier with a bit of risk.

The FIVE subversive and intentionally uncomfortable categories are tailored to spark meaningful conversation, shared vulnerability, and unexpected insight.

CATEGORIES: Spicy Confessions, Past Lives, Mirror Work, Trigger Warning, and Romance Round 2!

Real talk about second chances at love, adult intimacy, and all the weird, wonderful shit that comes with being human.

Don't just eavesdrop - try it! If you'd like a starter kit of playful heat, send a request to [email protected]

Let the awkwardness be part of the vibe.

If you have an inquiry or topic you’d like Jordan and J.T. to dig into, please send an email or voice memo to [email protected]

Enjoy the conversation? It would mean the world if you had a second to SHARE this episode - or your favorite episode! If you haven't already, please SUBSCRIBE/FOLLOW on the homepage at letsdigintothat.com or wherever you find your podcasts. THANK YOU, Love Ninjas! The impact of your support is greater than you can imagine.

Ever paid for that $40 DoorDash burrito in a sweaty delivery exchange and thought: Who am I, and what is this life? Modern convenience just might be killing our joy. If comfort were a drug, we'd all be addicted. If you're curious about what convenience might be doing to your curiosity, not to mention your capacity for emotional resilience and connection, join Jordan and J.T. to discover:

- How dopamine-on-demand is numbing our ability to feel real connection or desire

- The 5 Conveniences that Quietly Corrupt

- How does avoidance-based/one-click living impact our resilience and empathy?

- Does a comfort addiction make you an entitled asshole?

- What GPS does to our brains & the impact of engaging with strangers

- Is Amazon Prime the biggest threat to modern marriage?

- Suffering, friction, delays, and the recipe for real connection

- Convenience sex/instant swipe gratification: do we remember how to want or wait?

- Strategies to combat convenience culture

- Is there a connection between convenience dependence and anxiety?

- Climate Control: our literal and metaphorical need to feel good

If you have an inquiry or topic you’d like Jordan and J.T. to dig into, please send an email or voice memo to [email protected]

Enjoy the conversation? It would mean the world if you had a second to SHARE this episode - or your favorite episode! If you haven't already, please SUBSCRIBE/FOLLOW on the homepage at letsdigintothat.com or wherever you find your podcasts. THANK YOU, Love Ninjas! The impact of your support is greater than you can imagine.

One would hope we evolve, learn, and change over time, but can we outgrow our personality? What if you're only pretending to like spicy margaritas and karaoke? Has the Party Guy era come to a close? If you're staring at an unrecognizable vision board from 2018 or seeking permission to change your mind, join Jordan and J.T. for a raw discussion of personality. From identity and reinvention to trauma disguised in "that's just me" habits, listen to discover:

- What is personality? Your Enneagram? Your Spotify Wrapped? Your career title or coping style?

- Does all evolution/growth require a complete existential breakdown?

- The influence of outside perspective, external motivation, and validation

- The tension between branding yourself and being yourself

- Are we boxed in by our own stories? I'm the wild one...I'm the sensitive, empath.

- Are we allowed not to spiral? Is inner peace a thing?

- Why evolution feels both terrifying and liberating

- How to get comfortable with I don't know who I am right now

- Unconventional approaches to surviving the spiral

- The moments that prompted "wait, who am I?"

- Retiring roles: Do we grieve, burn, or feel free?

Literary Shout Out: Sheila Heti, How Should a Person Be? (Picador, 2012)

If you have an inquiry or topic you’d like Jordan and J.T. to dig into, please send an email or voice memo to [email protected]

Enjoy the conversation? It would mean the world if you had a second to SHARE this episode - or your favorite episode! If you haven't already, please SUBSCRIBE/FOLLOW on the homepage at letsdigintothat.com or wherever you find your podcasts. THANK YOU, Love Ninjas! The impact of your support is greater than you can imagine.

Whether it's your mental heath, or simple wellness practices, living an intentional and purposeful life starts within - and no one knows that better than Alyssa Scarano, Licensed Professional Counselor and Founder/Owner of The Collective Therapy & Wellness. Looking to swap external approval for internal validation, join and Jordan and J.T. as they learn Alyssa's techniques to cultivate real, meaningful connection in a fast paced digital world.

About ALYSSA:

Alyssa Scarano, LPC, NCC, is a Licensed Professional Counselor and the Founder/Owner of The Collective Therapy & Wellness. Known for her empathetic and compassionate approach, Alyssa views her work as a profound privilege—an opportunity to be invited into the most intimate and vulnerable parts of her clients’ lives to offer unwavering support and grace. Specializing in relationships, Alyssa is dedicated to helping individuals heal from childhood trauma, break generational patterns, and cultivate meaningful, authentic connections by first fostering a compassionate relationship with themselves.

If you have an inquiry or topic you’d like Jordan and J.T. to dig into, please send an email or voice memo to [email protected]

Enjoy the conversation? It would mean the world if you had a second to SHARE this episode - or your favorite episode! If you haven't already, please SUBSCRIBE/FOLLOW on the homepage at letsdigintothat.com or wherever you find your podcasts. THANK YOU, Love Ninjas! The impact of your support is greater than you can imagine.

Join Jordan and J.T. as they unzip their emotional fanny packs and lay bare their most anxious parts. J.T. shares details from his recent low-key little breakdown and his proactive approach to working with his overprotective anxiety.

Fun fact: Anxiety isn't brokenness; it's biology. From fight, flight, or freeze to shame in the sheets, it seems no one is immune.

Listen to discover:

- Low-impact, high-reward anxiety coping tools that work (...if implemented)

- Naming it, instead of shaming it: the power of saying "I'm anxious right now"

- Anxiety as the protector and the saboteur

- Lies our anxiety tells us

- When we pass off anxiety as intuition

- Where do you feel anxiety in your body? (Somatic reflection)

- Act! Go outside, rage dance, breathe, write, scream, skip...

- If your anxiety had a love language, what would it be?

DISCLAIMER: Let’s Dig into That is not a replacement for therapy. The advice, recommendations, and tips discussed are provided as thought-provoking, curiosity-poking insights aimed to inspire conversation, not as specific professional, therapeutic, or psychiatric guidance. Views and opinions expressed are from personal experience and perspective. Listener discretion is advised. Please seek the mental health care that best serves your needs.

If you have an inquiry or topic you’d like Jordan and J.T. to dig into, please send an email or voice memo to [email protected]

Enjoy the conversation? It would mean the world if you had a second to SHARE this episode - or your favorite episode! If you haven't already, please SUBSCRIBE/FOLLOW on the homepage at letsdigintothat.com or wherever you find your podcasts. THANK YOU, Love Ninjas! The impact of your support is greater than you can imagine.

It's time to talk money. Who's sweaty? Jordan and J.T. welcome Ed Vargo, the Co-Founder and CEO of Burning River Advisory Group and EnlightenHer, to discuss and demystify our finances. Ed believes a financial education shouldn’t make you feel small; it should make you feel powerful.

Ed’s passion for helping women with their finances stems from his childhood. His mother, an immigrant from South Korea, had four children with his father. After getting a divorce, she lost custody of her children due to her inability to support her family financially. Her unfortunate lack of financial literacy fueled Ed’s passion to empower women so that they can move through divorce confidently and without fear.

Listen to discover:

- How do we remove our emotional response to money so we can feel empowered when we manage our finances?

- Financial coaching: so, it doesn't need to be overwhelming, condescending, and confusing?

- The most damaging money myths we need to bust

- Raising financially educated kids

- Money scripts that aren't serving us and how to change them now

- Meaningful vs meaningless spending? When to have the talk?

- Ed's thoughts on combining finances. How about the second time around?

About Ed:

Ed Vargo is the Co-Founder and CEO of Burning River Advisory Group and EnlightenHer, a community focused on financial mentorship for women. With over 20 years in financial services, Ed helps women navigate long-term financial planning for all life stages, including retirement, college, and transitions related to divorce or death. His dedication is personal; inspired by his mother’s financial struggles after his parents' divorce, Ed is committed to empowering women to confidently manage their finances and avoid similar hardships. He is a member of the Financial Planning Association® and the Society of Financial Service Professionals. Ed is married with five daughters, ages 18-24, whom he has raised to be financially empowered young women!

If you have an inquiry or topic you’d like Jordan and J.T. to dig into, please send an email or voice memo to [email protected]

Enjoy the conversation? It would mean the world if you had a second to SHARE this episode - or your favorite episode! If you haven't already, please SUBSCRIBE/FOLLOW on the homepage at letsdigintothat.com or wherever you find your podcasts. THANK YOU, Love Ninjas! The impact of your support is greater than you can imagine.

The Season 3 Questions are in - THANK YOU for your boundless curiosity! Jordan and J.T. are ready for the gauntlet of vulnerability, prepped to flex a little bravery and self-compassion.

Join the conversation for a mix of sexy, spicy, and slightly uncomfortable questions intended to crack us open and connect us all.

If you have an inquiry or topic you’d like Jordan and J.T. to dig into, please send an email or voice memo to [email protected]

Enjoy the conversation? It would mean the world if you had a second to SHARE this episode - or your favorite episode! If you haven't already, please SUBSCRIBE/FOLLOW on the homepage at letsdigintothat.com or wherever you find your podcasts. THANK YOU, Love Ninjas! The impact of your support is greater than you can imagine.

Jordan and J.T. could not shake the idea that the alleged "end" of a relationship could be DIVORGASMIC, so they invited the Coach who coined the word to learn more. From the adjustment of being re-singled to giving yourself permission to seek joy, how can we better love and support each other in times of transition?

Karen McNenny, The Good Divorce Coach™, is changing the way families navigate divorce. We can agree that divorcing families are starved for better outcomes with less debt, destruction, and despair. Karen's signature Good Divorce Experience™ guides couples through the legal process of getting divorced, but more importantly, she teaches her clients HOW to be divorced. With her guidance, Karen’s clients learn to navigate the path of their divorce in a new way, with more hope for their family and compassion for themselves and their former spouse.

About KAREN:

Karen McNenny is a mediator, divorce coach, and therapist dedicated to transforming how families navigate divorce. Through her Good Divorce Experience™, she helps couples not only get divorced but also learn how to maintain healthy post-divorce relationships, especially when children are involved. With more than 25 years of expertise, Karen focuses on co-parenting, financial planning, and relationship literacy, guiding families toward compassionate outcomes. A TEDx speaker and host of the The Good Divorce Show Podcast™, Karen draws from her own divorce journey to offer hope and healing. She lives in Missoula, Montana, with her family and dog, enjoying the outdoors in the Rocky Mountains.

If you have an inquiry or topic you’d like Jordan and J.T. to dig into, please send an email or voice memo to [email protected]

Enjoy the conversation? It would mean the world if you had a second to SHARE this episode - or your favorite episode! If you haven't already, please SUBSCRIBE/FOLLOW on the homepage at letsdigintothat.com or wherever you find your podcasts. THANK YOU, Love Ninjas! The impact of your support is greater than you can imagine.

From fun-haters to play-daters, when did we stop prioritizing delight? Is it irresponsible for adults to play, or is fun essential for a fulfilling life? No idea what fun means to you anymore? You are not alone! Join the conversation to discover:

- The elements of True Fun: playfulness, connection, & flow

- When did fun start to feel more like a luxury than a birthright?

- Know thyself: how can we treat fun like a spiritual practice rather than a break from work?

- The evolution of fun: exposing false or toxic fun; does scheduling fun kill the vibe?

- What are the signs you're in the flow?

- Why does fun sometimes feel like guilt, shame, or rebellion?

- Retrospective fun vs. the pleasure of anticipation

- Fun disconnectors and disrupters (like J.T.'s FOMO)

- The duration and intensity of joy vs. pleasure

- Looking for a good time? Cheap and cheerful ideas: go outside, hike, bike, picnic, volunteer, free museums, library date, swim, (pretend) camp, go to the beach, farmer's market, games, scavenger hunt, sidewalk chalk!

Fun is not a crime. But if it were, we’d be on the run!

If you have an inquiry or topic you’d like Jordan and J.T. to dig into, please send an email or voice memo to [email protected]

Enjoy the conversation? It would mean the world if you had a second to SHARE this episode - or your favorite episode! If you haven't already, please SUBSCRIBE/FOLLOW on the homepage at letsdigintothat.com or wherever you find your podcasts. THANK YOU, Love Ninjas! The impact of your support is greater than you can imagine.

WOW! Buckle up, Love Ninjas, because Dr. Adam Dorsay is in the house! Silicon Valley's licensed psychologist, executive coach, author, and podcast host delivers mic-drop insights from his book Super Psyched: Unleash the Power of the 4 Types of Connection & Live the Life You Love.

This book changes the game. Join Jordan and J.T. as they dig into connection with the author himself. From his highly regarded TEDx Talks, lively keynotes, and award-winning podcast Super Psyched, Adam is the guru of gusto. Starting with a connection to self, determine what fills your cup. Adam shares his Connection Formula, a personalized prescription for a more fulfilling life. Don't miss the magic!

**If you're in a music rut, inspiration awaits!

THE MAN: Doting husband, father of two boys, and recent cat-loving convert. Connect with Adam on his website DrAdamDorsay.com, tune in for the podcast Super Psyched, and if you haven't already, treat yo'self and BUY THE BOOK!

THE BOOK: Adam Dorsay, PsyD, Super Psyched: Unleash the Power of the 4 Types of Connection & Live the Life You Love (Amplify, 2024)

THE MUSIC: George Michael, Prince, Rush, Wham!, Taylor Hawkins of The Foo, Enya...

If you have an inquiry or topic you’d like Jordan and J.T. to dig into, please send an email or voice memo to [email protected]

Enjoy the conversation? It would mean the world if you had a second to SHARE this episode - or your favorite episode! If you haven't already, please SUBSCRIBE/FOLLOW on the homepage letsdigintothat.com or wherever you find your podcasts. THANK YOU, Love Ninjas! The impact of your support is greater than you can imagine.