Dave Glaser
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...
Where to listen?
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Episodes
Living with Strength, Vulnerability & Trust as the Type 8 Father 30.06.2025 16:16
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 vulnerable dive into what happens when the protector becomes present, not just powerful. As a follow up to last week's episode, host Dave Glaser invites The Challenger to look inward for answers and growt...
Power, Presence & Fatherhood: A Type 8's Path to Self-Leadership 23.06.2025 24:42
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 natural leaders. But how does this personality navigate the emotional landscape of parenting, especially when trying to lead with empathy, grace, and growth? We'll unpack how self-leadership and inner wo...
How to Use the Enneagram as a Type 9- The Peacemaker 30.01.2025 24:37
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 guide you through how to learn about yourself through your Ennegram type using The Peacemaker, type 9, as an introduction to the fun and amazing tool for self-awareness. Don't know your type? Click 9ty...
How to use the Enneagram for The Peacemaker, type 9 Video 04.12.2024 24:37
In today's video, 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 guide you through how to learn about yourself through your Ennegram type using The Peacemaker, type 9, as an introduction to the fun and amazing tool for self-awareness. Don't know your type? Click 9type...
Hinge Prompts for the Enneagram 5 plus Politics in Dating 22.07.2024 59:59
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 saves you time and heartbreak. What are your thoughts? On today's episode of the podcast, I lay out a few answers to those questions and so much more. For starters, I cover how the Enneagram 5, the In...
Living a Sober Life with Kyle Weiger 15.07.2024 1:05:12
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 resonates with you today, please connect with him on all social media platforms @kyleweiger or kyleweiger.com Did you enjoy the podcast? If so, please leave a review on Apple Podcasts and Spotify, It helps...
The Best Hinge Prompts for the Enneagram Type 4; The Individualist 08.07.2024 1:02:00
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 Hinge prompts if you're an Enneagram type 4, The Individualist. Are you a 4 or dating an Individualist? These prompts will help you understand yourself and others when dating online in the modern world....
The Best Hinge Prompts for Enneagram 3s: The Achiever 17.06.2024 45:16
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. Are you a 3 or dating an Achiever? These prompts will help you understand yourself and others when dating in the modern world. We close out today's episode by talking about Cults; specifically the C...
The Best Hinge Prompts for Enneagram 2s: The Helper 10.06.2024 30:00
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 scammer on a dating app! I have also discovered a few tips on what to do to prevent being scammed or victimized financially when dating online. More topics in this episode are life updates you may not...
The Best Hinge Prompts for an Enneagram Type 1 25.03.2024 9:40
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, Reformer? In today's mini episode, I share some of the prompts that an Enneagram type 1 would choose to show their authentic self on Hinge. Plus the answers they may come up with to have fun when dati...
Choosing Hinge Prompts for the Enneagram Type 9 11.03.2024 8:41
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. Plus the answers they may come up with to have fun when dating online. Did you enjoy the podcast? If so, please leave a review on Apple Podcasts and Spotify, It helps us get into the ears of new listeners...
Picking Hinge Prompts for the Enneagram Type 8 04.03.2024 7:33
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 answers they may come up with to have fun when dating online. Did you enjoy the podcast? If so, please leave a review on Apple Podcasts and Spotify, It helps us get into the ears of new listeners, expa...
Match.com Class Action Lawsuit 21.02.2024 22:18
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 the impact on users and the broader implications for online dating platforms. Tune in for a comprehensive analysis of this high-profile case that has sparked conversations about data privacy, user protec...
3 Reasons You're Getting Friendzoned 17.07.2023 16:49
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 being agreeable is generally seen as positive, excessive agreeableness can sometimes be perceived as lacking individuality or assertiveness, which may reduce attraction. Dr. David Buss, a prominent evo...
Can You Be Attached to Money with Jordan Pendleton Video 19.06.2023 50:15
Can we be too attached to our money? On this week's episode of the podcast, Jordan Pendleton joins me as guest host where she interviews me on how our attachment styles show up to influence our relationship with money. I truly enjoyed this conversation with her on her podcast REAL Money Talk as she asked great questions about my journey from scarcity to abundance in life, money and relation...
10 Signs Your Date has an Avoidant Attachment Style Video 12.06.2023 25:51
On this week's episode, I lay out ten things to look out for on a first date that can tell you that your date has an avoidant attachment style. In tune last week's episode, I'd like to encourage everyone to be mindful in how they approach making assumptions about their date and instead of writing them off as red flags, get curious about what you see and label the behavior. Did you enjoy the podca...
If He Wanted To, He Would with Samantha Graham Video 05.06.2023 1:01:17
On this week's episode of the podcast, I am joined by Samantha Graham, cohost of Where's Our Participation Trophy podcast, to talk about modern dating from the lens of attachment theory. The title of this podcast comes from viral videos and memes on the internet which can feel confusing for daters in the modern world being told that the right person would be able to read your mind and just give...
10 Signs Your Date has an Anxious Attachment Style Video 29.05.2023 35:09
On this week's episode, I walk you through 10 signs that your date or partner may have an anxious attachment style. Attachment theory research has been evolving since the last 60s and I discovered its impact in my life about five years ago. After a couple of bad breakups in 2017, I decided to make a change and took ownership of my role in the ending of those relationships. I sought out a counsel...
Why You Attract Emotionally Unavailable People with Talia Bombola 08.05.2023 52:51
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 the podcast, Talia and I dug in to attachment styles, masculine and feminine energy dynamics and so much more. This time around, I asked three questions that are most common in our community of authen...
Should a Woman Ask Out a Man? 24.04.2023 6:13
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 on this six minute episode and reach out with any questions you may have about flirting with the masculine in a playful to let him know you're interested. Did you enjoy the podcast? If so, please leave...
Dating After Divorce with An Anxious Attachment Style with Becky Bradley 27.03.2023 59:12
On this week's episode of the podcast, we continue on with our series on first dates with a real life dater Becky Bradley. I am so impressed with her bravery to come speak with me on the podcast about dating after divorce with an anxious attachment style. We dig into Becky's life story beginning with a medical condition as a child that left her feeling alone in school and isolated from her friend...
How to Define Your Relationship with Dave Glaser 15.03.2023 15:01
How do you define the relationship? This week's episode is a live conversation originally recorded on Tiktok with our community contributing questions as we dig into the definition of a relationship agreement vs defining the relationship with terms such as boyfriend and girlfriend. The conversation turned to attachment theory and the differnces of how defining the relationship impacts the nervous...
Why The "Nice Guy" is Not So Nice with Traver Boehm 06.03.2023 1:29:07
What is "Nice Guy" Syndrome? I've seen the Nice Guy show up in my past and have experienced a lot of growth in the past few years when facing those tendencies and integrating that part back into my psyche. On this week's episode, Traver joins me to educate us on how the Nice Guy shows up for men in relationships. Traver Boehm @traverboehm is a former MMA fighter, a Challenger on the Enneagram...
Are We Dating the Same Guy with Britt Leilani 27.02.2023 40:32
Recored live on Tiktok, I am joined this week by real life dater, Britt Leilani from Boise, Idaho. Britt and I discuss a growing phenomenon in modern dating; Facebook groups connecting people over whether or not they are dating the same person. Are you a member of one of these groups in your area? Britt is a member of two groups as she travels 6 months out of the year between D.C. and Boise wher...
Where Do Men Go Wrong with GS Youngblood Video 13.02.2023 51:27
I'm celebrating 250 episodes with a replay of one of the most popular epidoses! On this week's episode of the podcast, we welcome back GS Youngblood to the program to talk all things embodiment and how men show up in relationship. GS is the author of The Masculine in Relationship and is set to dive deeper into embodiment practices with his new work. Before we recorded, I polled our listeners...
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