Stop Repeating Old Patterns! Divorce Recovery for Men 40+ || Attachment Theory Deep Dive || CT Kaupp

32min | 01/17/2026

Description

Welcome to the Don’t Pick the Scab Podcast—the place where men over 40 find their path to real healing and personal growth after divorce. I’m David, your host, and today’s episode is a true game-changer for anyone feeling stuck in the same old relationship patterns, confused by the emotional rollercoaster of dating after divorce, or simply wanting to break free and build something better.

In this powerful conversation, I’m joined by CT Kaupp, a relationship and attachment style coach who has personally transformed heartbreak into wisdom. CT’s journey—from years of anxiousness and overthinking to genuine self-awareness—holds the key for men like us who are ready to stop “fixing” partners and start understanding ourselves.

What You’ll Learn:

Attachment Styles 101: Discover the four main attachment styles—secure, anxious, dismissive avoidant, and fearful avoidant—and how they secretly shape your relationships from childhood through every date post-divorce.
Why We Repeat Unhealthy Cycles: Learn why so many men over 40 find themselves stuck with the same types of partners and how self-awareness can finally break the cycle.
The Anxious-Avoidant Trap: Get the real talk about why opposites attract but often crash, and how to spot this dynamic before it derails your next relationship.
Boundaries, Expectations & Self-Care: Practical strategies for setting healthy boundaries, communicating your needs confidently, and practicing self-care that actually works (especially for anxious types!).
Love Languages & Miscommunication: How understanding love languages can save your next relationship—and why so many divorces are rooted in simple misunderstandings.
Dating After Divorce: Red flags and green flags to spot different attachment styles in online dating, plus tips for men who want to move from “insecure” to “secure” in their relationships.
Co-Parenting & Attachment: How your attachment style might impact your co-parenting approach and what to watch for as a dad post-divorce.

CT brings compassion, actionable advice, and hard-earned wisdom to help men stop overthinking, boost their self-esteem, and create the connections they truly want. If you’re tired of buzzwords and want real, practical tools to rewire your relationship habits—this episode is for you. 🛠️

If you found this episode helpful, please hit LIKE, SUBSCRIBE, and SHARE with another guy who needs this message. 💬 Drop a comment below: What’s your biggest challenge when it comes to dating or healing after divorce? Let’s start the conversation and support each other!

CT's Website

CT on Spotify

CT on Instagram

#DivorceRecovery #MenOver40 #AttachmentStyles #RelationshipAdvice #DontPickTheScab #HealingAfterDivorce

Hosted on Ausha. See ausha.co/privacy-policy for more information.

About DON'T PICK THE SCAB PODCAST

Success, Divorce, and Reinvention—You’re Not Alone.

Divorce can shake even the most accomplished men to their core, no matter their age or status. The end of a marriage is often an emotionally and mentally taxing experience, especially for successful men who are accustomed to thriving in other areas of life. That’s why the "Don't Pick the Scab Podcast" is here: a safe, open platform where successful men recovering from divorce can share their stories, find support, and gain practical tools for rebuilding.

Success doesn’t make divorce any easier. When you’re used to winning, starting over—emotionally, financially, and socially—can feel like uncharted territory. The challenges of re-establishing your identity and navigating new roles after a significant breakup are real, but you don’t have to face them alone.

Each episode dives into authentic conversations with men who have walked this path—from entrepreneurs and executives, to leaders in their fields. We explore the unique hurdles successful men encounter during divorce, from managing public perception and careers to processing the deeply personal emotions of grief, regret, anger, and hope. Alongside expert guests, we offer practical advice and proven strategies for healing and growth.

This podcast is about more than just surviving divorce—it’s about thriving in your next chapter. Through shared experiences and actionable insights, "Don't Pick the Scab Podcast" aims to help you rediscover meaning, rebuild confidence, and create a life filled with new possibilities.

Join us each week as we walk the road to recovery, together. Let’s break the stigma, embrace vulnerability, and support one another on the journey to a brighter, more successful future after divorce.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

About DON'T PICK THE SCAB PODCAST

Success, Divorce, and Reinvention—You’re Not Alone.

Divorce can shake even the most accomplished men to their core, no matter their age or status. The end of a marriage is often an emotionally and mentally taxing experience, especially for successful men who are accustomed to thriving in other areas of life. That’s why the "Don't Pick the Scab Podcast" is here: a safe, open platform where successful men recovering from divorce can share their stories, find support, and gain practical tools for rebuilding.

Success doesn’t make divorce any easier. When you’re used to winning, starting over—emotionally, financially, and socially—can feel like uncharted territory. The challenges of re-establishing your identity and navigating new roles after a significant breakup are real, but you don’t have to face them alone.

Each episode dives into authentic conversations with men who have walked this path—from entrepreneurs and executives, to leaders in their fields. We explore the unique hurdles successful men encounter during divorce, from managing public perception and careers to processing the deeply personal emotions of grief, regret, anger, and hope. Alongside expert guests, we offer practical advice and proven strategies for healing and growth.

This podcast is about more than just surviving divorce—it’s about thriving in your next chapter. Through shared experiences and actionable insights, "Don't Pick the Scab Podcast" aims to help you rediscover meaning, rebuild confidence, and create a life filled with new possibilities.

Join us each week as we walk the road to recovery, together. Let’s break the stigma, embrace vulnerability, and support one another on the journey to a brighter, more successful future after divorce.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

Description

Welcome to the Don’t Pick the Scab Podcast—the place where men over 40 find their path to real healing and personal growth after divorce. I’m David, your host, and today’s episode is a true game-changer for anyone feeling stuck in the same old relationship patterns, confused by the emotional rollercoaster of dating after divorce, or simply wanting to break free and build something better.

In this powerful conversation, I’m joined by CT Kaupp, a relationship and attachment style coach who has personally transformed heartbreak into wisdom. CT’s journey—from years of anxiousness and overthinking to genuine self-awareness—holds the key for men like us who are ready to stop “fixing” partners and start understanding ourselves.

What You’ll Learn:

Attachment Styles 101: Discover the four main attachment styles—secure, anxious, dismissive avoidant, and fearful avoidant—and how they secretly shape your relationships from childhood through every date post-divorce.
Why We Repeat Unhealthy Cycles: Learn why so many men over 40 find themselves stuck with the same types of partners and how self-awareness can finally break the cycle.
The Anxious-Avoidant Trap: Get the real talk about why opposites attract but often crash, and how to spot this dynamic before it derails your next relationship.
Boundaries, Expectations & Self-Care: Practical strategies for setting healthy boundaries, communicating your needs confidently, and practicing self-care that actually works (especially for anxious types!).
Love Languages & Miscommunication: How understanding love languages can save your next relationship—and why so many divorces are rooted in simple misunderstandings.
Dating After Divorce: Red flags and green flags to spot different attachment styles in online dating, plus tips for men who want to move from “insecure” to “secure” in their relationships.
Co-Parenting & Attachment: How your attachment style might impact your co-parenting approach and what to watch for as a dad post-divorce.

CT brings compassion, actionable advice, and hard-earned wisdom to help men stop overthinking, boost their self-esteem, and create the connections they truly want. If you’re tired of buzzwords and want real, practical tools to rewire your relationship habits—this episode is for you. 🛠️

If you found this episode helpful, please hit LIKE, SUBSCRIBE, and SHARE with another guy who needs this message. 💬 Drop a comment below: What’s your biggest challenge when it comes to dating or healing after divorce? Let’s start the conversation and support each other!

CT's Website

CT on Spotify

CT on Instagram

#DivorceRecovery #MenOver40 #AttachmentStyles #RelationshipAdvice #DontPickTheScab #HealingAfterDivorce

Hosted on Ausha. See ausha.co/privacy-policy for more information.

About DON'T PICK THE SCAB PODCAST

Success, Divorce, and Reinvention—You’re Not Alone.

Divorce can shake even the most accomplished men to their core, no matter their age or status. The end of a marriage is often an emotionally and mentally taxing experience, especially for successful men who are accustomed to thriving in other areas of life. That’s why the "Don't Pick the Scab Podcast" is here: a safe, open platform where successful men recovering from divorce can share their stories, find support, and gain practical tools for rebuilding.

Success doesn’t make divorce any easier. When you’re used to winning, starting over—emotionally, financially, and socially—can feel like uncharted territory. The challenges of re-establishing your identity and navigating new roles after a significant breakup are real, but you don’t have to face them alone.

Each episode dives into authentic conversations with men who have walked this path—from entrepreneurs and executives, to leaders in their fields. We explore the unique hurdles successful men encounter during divorce, from managing public perception and careers to processing the deeply personal emotions of grief, regret, anger, and hope. Alongside expert guests, we offer practical advice and proven strategies for healing and growth.

This podcast is about more than just surviving divorce—it’s about thriving in your next chapter. Through shared experiences and actionable insights, "Don't Pick the Scab Podcast" aims to help you rediscover meaning, rebuild confidence, and create a life filled with new possibilities.

Join us each week as we walk the road to recovery, together. Let’s break the stigma, embrace vulnerability, and support one another on the journey to a brighter, more successful future after divorce.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

About DON'T PICK THE SCAB PODCAST

Success, Divorce, and Reinvention—You’re Not Alone.

Divorce can shake even the most accomplished men to their core, no matter their age or status. The end of a marriage is often an emotionally and mentally taxing experience, especially for successful men who are accustomed to thriving in other areas of life. That’s why the "Don't Pick the Scab Podcast" is here: a safe, open platform where successful men recovering from divorce can share their stories, find support, and gain practical tools for rebuilding.

Success doesn’t make divorce any easier. When you’re used to winning, starting over—emotionally, financially, and socially—can feel like uncharted territory. The challenges of re-establishing your identity and navigating new roles after a significant breakup are real, but you don’t have to face them alone.

Each episode dives into authentic conversations with men who have walked this path—from entrepreneurs and executives, to leaders in their fields. We explore the unique hurdles successful men encounter during divorce, from managing public perception and careers to processing the deeply personal emotions of grief, regret, anger, and hope. Alongside expert guests, we offer practical advice and proven strategies for healing and growth.

This podcast is about more than just surviving divorce—it’s about thriving in your next chapter. Through shared experiences and actionable insights, "Don't Pick the Scab Podcast" aims to help you rediscover meaning, rebuild confidence, and create a life filled with new possibilities.

Join us each week as we walk the road to recovery, together. Let’s break the stigma, embrace vulnerability, and support one another on the journey to a brighter, more successful future after divorce.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

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