Date Fails -pilot

Explicit content warning

01/21/25 • 39 min

CHAPTERS / TIMESTAMPS
00:04 - The Introduction & My Impromptu Episode Style
01:21 - A Huge Thank You to My Listeners
01:49 - Why I Decided to Share My Dating Fails
03:47 - The First Breakup That Started It All
04:41 - The Audition That Could’ve Changed My Life
06:27 - The Ultimatum That Forced a Big Decision
09:04 - Rejecting a Million-Peso Contract for Love
10:11 - Dealing with Loneliness Post-Breakup
11:28 - My First Online Dating Experience - A Wake-Up Call
12:22 - The Mysterious Disappearance of My Date
14:27 - Was I Catfished? Signs I Ignored
16:06 - Getting Back Together & Realizing the Truth
17:37 - Another Online Dating Disaster - Meet Whitney
19:22 - The Premium Dating App Experiment (Tinder, POF, Match, Zoosk)
21:38 - Falling for Someone I Never Met in Person
24:18 - The Build-Up to the Date That Never Happened
26:25 - Excuses, Cancellations & Red Flags
29:19 - The Reality Check: What Really Happened
30:13 - Why Sharing These Stories Matters
33:24 - Why I Use Humor & Storytelling for Mental Clarity
36:35 - Final Thoughts & The Future of This Series
This episode explores my funniest and most embarrassing dating fails. Through humorous anecdotes, I reflect on past relationships, emotional connections, and the harsh lessons learned along the way, reinforcing the importance of resilience and self-awareness in the dating world.
• Sharing gratitude for listener support
• Framing dating disasters as an opportunity for growth
• Encountering an ultimatum and important life decisions
• First experiences with online dating and catfish suspicions
• Exploring emotional connections before physical interactions
• Reflecting on the mix of humor and vulnerability in dating
• Engaging with listeners and inviting them to share their stories
What happens when you have to choose between love and a career opportunity on opposite sides of the globe? Join me as I spill the details of navigating the tricky waters of long-distance relationships and career decisions, all while sharing some of my most hilarious and cringe-worthy dating stories. From debating whether to pursue a job in the Philippines or stay for a budding romance in Calgary, to the emotional chat that led to going exclusive with my ex, you'll hear about the highs and lows of balancing heart and ambition.
Ever texted someone for a month, only to find they’re allergic to meeting in person? That's what happened with Whitney, a digital romance that was full of emotional texting but hit a roadblock at the physical meetup stage. Tune in for a tale of hope and surprise plot twists, like a contrived emergency before a first date.

Support the show

Access Tailored Insights for Exclusive Supporters
https://openinapp.link/dcdpu
Linktree
https://openinapp.link/pw9ew
YouTube
https://yt.openinapp.co/h1hhu
Instagram
https://insta.openinapp.co/sck1a
Apple Podcasts
https://apple.openinapp.link/zk0yu
Spotify
https://spotify.openinapp.co/7ll7r
TikTok
https://openinapp.link/zs0zh
Threads
https://openinapp.co/oe9xn
OR Buy me a Whopper! :)
https://openinapp.link/rv6zh

Send us a text

Support the show

Previous Episode

i Defend Allison Holker -heavy

Send us a text

CHAPTERS / TIMESTAMPS
0:00 - Introduction & Support for the Channel
- Transparency & deep-thinking community discussion begins

1:40 - Why I Had to Talk About Allison & Twitch
- Unpacking the layers of the story

3:55 - The Internet’s Outrage Against Allison Holker
- Why is the backlash so intense?

5:20 - False Allegations, Truth-Twisting & Profit
- False claims for fame & money?
- Mental Health Struggles
7:43 - The Risk of Jumping to Conclusions
- Why we must be careful with outrage
10:17 - The "Wiggle Room" Dilemma in Cancel Culture
- The long-term impact of not allowing mistakes
12:46 - Twitch’s Private Struggles: What We Didn’t See
- The hidden pain behind public smiles
- Neglect, frustration & depression
13:37 - Role of Mental Health in Allison’s Perspective
- Depression, how it leads to desperation
- Was Allison acting irrationally from emotional distress?
14:35 - Social Media vs. Reality
- Struggles of mental health behind curated content
16:11 - Was Twitch a Different Person at Home?
- How long-term emotional neglect can damage relationships
17:53 - Financial Struggles & Life Insurance Speculation
- What happens when a primary provider is gone?
19:50 - The Ethics of Monetizing Personal Tragedy
- OnlyFans and GoFundMe
21:48 - What Would YOU Do in Allison’s Shoes?
- How grief influences desperate decisions
23:00 - Public Outrage: Real or Performative?
- Pause before reacting
25:35 - Life Goes On, Even After Tragedy
- Struggles & dealing with loss
27:25 - The Long-Term Consequences
- Long-term plans
28:34 - Deeper Reflection & Compassion
- We must think before reacting
36:32 - Twitch’s Friends & Family
- Anyone see it coming?
39:47 - Synthetic Social Media Support
- The disconnect between online & real-life relationships
44:53 - Checking In On Loved Ones
- Pride & fear in asking for help
48:27 - The "What If" Syndrome
- Did people close to Twitch blame themselves?
51:52 - Problem With Performative Grief
- Fake outrage
- Practicing what we preach in our own lives
56:21 - Reality of Losing Someone Without Support
- Creating stronger support systems
1:06:32 - Truth About Relationship Tensions & Hidden Struggles
- Unseen daily struggles behind fame & marriage
1:17:03 - The Importance of Looking at Every Angle
- Diagnosing past tragedies to prevent future ones
1:24:04 - Closing Thoughts: A Call for Fairness & Accountability
- Giving Allison & Twitch’s story a fair analysis
1:29:35 - Outro: Stay Connected

Support the show

Next Episode

30 Bodies at 19?! -Date Fails

Send us a text

CHAPTERS / TIMESTAMPS
0:00 - Intro | Late-night thoughts & shameless plugs
1:51 - Reflecting on heavy topics | Processing emotions & past relationships
2:48 - Why introverts thrive at night | Deep-thinking & creativity
4:01 - Introduction to the failed dating saga | The dating scene through my eyes
6:04 - Christine enters the chat | The setup & first impressions
8:54 - First date tension | When conversations don’t flow
9:51 - The unexpected third wheel | A sudden twist
10:34 - The awkward silence before the storm | When things take a turn
13:30 - The ultimate betrayal | When your date makes out with someone else
15:46 - How do you react? | Processing unexpected rejection
17:57 - A surprising dance battle | An unexpected reunion
20:33 - Shocking revelation | The 30-body count bombshell
23:44 - Relationship dealbreakers | When numbers make you pause
25:51 - The weird push-and-pull of dating games | Why do people act like this?
27:04 - Why do women do this?! | The confusing dynamics of dating
29:23 - Final thoughts & reflections | The evolution of modern dating
32:11 - Closing remarks & community questions | Let’s talk!
This episode explores the humorous and awkward dynamics of a blind date that led to unexpected makeouts and dating confusion. As we recount personal stories from past relationships, we dissect the complexities of modern dating culture and the unpredictable games that come with it.
• The impact of communication on relationship dynamics
What sparks creativity when the world goes quiet and the clock strikes midnight? Join me as I unravel the nocturnal musings that fuel my inspiration, sharing insights from a candid conversation with Carlo on why night owls like us find the silence so magical. This episode takes a heartfelt turn as I recount my awkward first meeting with a woman named Christine—sharing the same name as my wife—and the nervous excitement that surrounded it. It's a continuation of my journey through failed dating experiences, offering reflections on personal growth and the invaluable lessons learned from relationships past.
As the night deepens, we navigate the tangled web of modern dating, peppered with confusing encounters and mixed signals. Relive an evening of uncertainty that spirals into frustration, exploring themes of attraction, personal boundaries, and the perplexing dynamics of today's dating scene. With anecdotes that balance humor and introspection, I invite you to ponder your own relationship misadventures and the growth they provoke. Tune in for a blend of light-hearted reminiscence and serious reflection, promising both entertainment and insight into the trials and triumphs of human connection.