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The Challenger Podcast - Podcast

The Challenger Podcast

The Challenger Podcast helps you show up authentically and navigate modern dating where texting, social media and dating apps have become the way people connect and communicate.
Each week, I interview dating experts and real life daters is to share what authentic dating can look like for you in these modern times. New episodes and live recordings every other week to find your ideal relationship through the Enneagram, attachment theory and core energy dynamics. Subscribe and leave a rating and review today so that you never miss an episode and connect with me on Tiktok @dave.glaser for a candid look at modern dating.

Dating Advice Society & Culture Love Relationships
Update frequency
every 5 days
Average duration
38 minutes
Episodes
105
Years Active
2018 - 2025
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The Good, The Bad & The Ugly of a Type 9 in Relationship

The Good, The Bad & The Ugly of a Type 9 in Relationship

The Enneagram 9, often called The Peacemaker, is known for their calm, grounded, and accepting nature. But what does this really look like in a relationship — when it’s healthy, when it’s struggling,…

00:08:37  |   Mon 18 Aug 2025
The Good, The Bad & The Ugly of a Type 8 in Relationship

The Good, The Bad & The Ugly of a Type 8 in Relationship

This episode explores how the Enneagram 8 shows up in relationships; the good, the bad and the ugly with real life examples from remodeling a bathroom to fostering a dog... all in the same week!

As a…

00:10:25  |   Mon 11 Aug 2025
Why Putting Yourself First Makes You a Better Dad as an Enneagram 8

Why Putting Yourself First Makes You a Better Dad as an Enneagram 8

As an Enneagram 8 father, you're wired for strength, protection, and relentless loyalty to your family. But what happens when that loyalty causes you to neglect your own needs? In this episode, we ex…

00:11:23  |   Mon 28 Jul 2025
Parenting Through a Different Lens: How Type 8s can so up for each of the enneagram types

Parenting Through a Different Lens: How Type 8s can so up for each of the enneagram types

As an Enneagram 8 father, your strength and protectiveness are incredible gifts—but not every child experiences that big energy the same way.

In this episode of The Protective Leader, we explore how …

00:15:54  |   Mon 14 Jul 2025
Helping Your Children Flourish as a Type 8 Parent

Helping Your Children Flourish as a Type 8 Parent

This episode explores parenting and nuturing your child's indivuality through the powerful lens of the Enneagram Type 8—often known as “The Challenger.” Known for strength, assertiveness, and protect…

00:11:30  |   Mon 07 Jul 2025
Living with Strength, Vulnerability & Trust as the Type 8 Father

Living with Strength, Vulnerability & Trust as the Type 8 Father

This episode explores how Enneagram 8 fathers can build deeper emotional connections by developing trust, tenderness, and emotional fluency—without feeling like they’re giving up strength. It’s a vul…

00:16:16  |   Mon 30 Jun 2025
Power, Presence & Fatherhood: A Type 8’s Path to Self-Leadership

Power, Presence & Fatherhood: A Type 8’s Path to Self-Leadership

This episode explores fatherhood and leadership through the powerful lens of the Enneagram Type 8—often seen as “The Challenger.” Known for strength, assertiveness, and protectiveness, Type 8s are na…

00:24:42  |   Mon 23 Jun 2025
How to Use the Enneagram as a Type 9- The Peacemaker

How to Use the Enneagram as a Type 9- The Peacemaker

In today's episode, I will walk you through how to use the Ennegram as a tool to show up more authentically at work, with family and in relationships. Have you heard of The Enneagram?

 Today, I will …

00:24:37  |   Thu 30 Jan 2025
Hinge Prompts for the Enneagram 5 plus Politics in Dating

Hinge Prompts for the Enneagram 5 plus Politics in Dating

Do politics and dating go together? Some would say avoid talking about politics at all costs on a first date.

Others may try to convince you that discovering that about your date as early as possible…

00:59:59  |   Mon 22 Jul 2024
Living a Sober Life with Kyle Weiger

Living a Sober Life with Kyle Weiger

Kyle Weiger, hand balancing coach and good friend, joins me on the podcast today to talk about the home buying process, moving, job changes, sobriety and the Presidential Debates.

If his message reso…

01:05:12  |   Mon 15 Jul 2024
The Best Hinge Prompts for the Enneagram Type 4; The Individualist

The Best Hinge Prompts for the Enneagram Type 4; The Individualist

How do you set your intentions before you begin online dating? My top seven recommendations are available on today's episode of the podcast.  

We dig deep in this episode and how you would choose Hin…

01:02:00  |   Mon 08 Jul 2024
The Best Hinge Prompts for Enneagram 3s: The Achiever

The Best Hinge Prompts for Enneagram 3s: The Achiever

How do you spot red flags on a dating app? The top six answers are discussed on today's episode of the podcast.  

More topics in this episode are Hinge prompts for the Enneagram type 3, The Achiever.…

00:45:16  |   Mon 17 Jun 2024
The Best Hinge Prompts for Enneagram 2s: The Helper

The Best Hinge Prompts for Enneagram 2s: The Helper

How to tell if someone is scamming you or are a bot on a dating app? The quick answer is to ask them to spell "potato".  

The real answer is much more complex and I am here to share five signs of a s…

00:30:00  |   Mon 10 Jun 2024
The Best Hinge Prompts for an Enneagram Type 1

The Best Hinge Prompts for an Enneagram Type 1

The Reformer or Moral Protagonist, type 1, on the Enneagram is likely not the most creative or vulnerable person on your dating app.  

What are the likely prompts you'd see on Hinge for the Type 1, R…

00:09:40  |   Mon 25 Mar 2024
Choosing Hinge Prompts for the Enneagram Type 9

Choosing Hinge Prompts for the Enneagram Type 9

What are the best responses to popular Hinge prompts for the Peacemaker?  In today's mini episode, I share some of the prompts that an Enneagram type 9 would choose to show their authentic self.  Plu…

00:08:41  |   Mon 11 Mar 2024
Picking Hinge Prompts for the Enneagram Type 8

Picking Hinge Prompts for the Enneagram Type 8

Having a hard time picking prompts to use on the dating app Hinge?  In today's mini episode, I share some of the prompts that an Enneagram type 8 would choose to show their authentic self.  Plus the …

00:07:33  |   Mon 04 Mar 2024
Match.com Class Action Lawsuit

Match.com Class Action Lawsuit

In this episode, we delve into the intricate details of the Match.com class action lawsuit, exploring the implications and repercussions of the legal battle on modern dating. Join me as we uncover th…

00:22:18  |   Wed 21 Feb 2024
3 Reasons You're Getting Friendzoned

3 Reasons You're Getting Friendzoned

The top three reasons you may be getting FRIENDZONED are:

Agreeableness, availability, and accessibility can potentially decrease attraction in dating due to various reasons:

1. Agreeableness: While …

00:16:49  |   Mon 17 Jul 2023
Why You Attract Emotionally Unavailable People with Talia Bombola

Why You Attract Emotionally Unavailable People with Talia Bombola

On this week's episode of the podcast, Talia Bombola joins me for a follow up conversation to share with you why you may be attracted to and attracting emotionally unavailable people.  Previously on …

00:52:51  |   Mon 08 May 2023
Should a Woman Ask Out a Man?

Should a Woman Ask Out a Man?

This week, we have a quick hitting, solo episode where I dig into this popular quesiton from one of our audience members from a recent Tiktok Live.

Should a woman ask out a man on a date?  Listen in …

00:06:13  |   Mon 24 Apr 2023
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