The Bert Show: Vault - He's Afraid He's Going To Self Sabotage His New Relationship

Date: January 26, 2026
Host: Pionaire Podcasting
Main Cast in Episode: Bert (A), Kristin (B), Abby (C), Blake (D, Guest/Blogger)
Theme: Navigating New Relationships and Commitment Issues from a Guy’s Perspective

Episode Overview

This episode welcomes back "Blake", the show’s anonymous single-guy blogger, for a candid conversation about dating, self-sabotage, and the pressures of starting a new relationship—especially when family ties raise the stakes. Blake talks about his new love interest (“Diana”), struggles with changing his dating habits, and reflects on why commitment can be tough for men. The hosts and Blake delve into gender expectations, dating mind games, and the awkward dance of labels and exclusivity.

Key Discussion Points and Insights

Introducing “Blake” and His Situation

• Blake’s Role:

  • Blake is the show’s single anonymous guy blogger, offering honest insight into dating life in Atlanta.
  • “Because Blake is not actually his name. That is just going to be his pen name for coming on the Bird show so we can get some real honest, you know, honest insight into the dating world.” (B, 00:03)

• Blake’s New Situation:

  • He’s recently been set up with “Diana,” his sister-in-law’s lifelong best friend, making things both exciting and risky.
  • “...if I screw up, if I make a wrong move or if I offend someone...when you’re dealing with someone who you have a little respect for and you think of as a good person and a sweet girl, you can’t get off the telephone after having a screaming match and say, you know that B. I can’t believe her. She’s so wrong about this. You hang up the phone and you say, yeah, she’s…kind of right. I was kind of a jerk. And that’s not fun.” (D, 07:47)

Navigating Family Dynamics and Dating Anxiety

• High Stakes Family Connections:

  • Dating Diana introduces unique pressure because a mistake could affect family relationships.
  • “I just don’t want to tick off, you know, the kind of the newlywed wife…you can see that the family has definitely shifted. And…the last thing I need to do is lose my, you know, lose my ace in the hole.” (D, 02:58)

• Authenticity Over “Game”:

  • Blake usually keeps a defensive front early in dating to avoid being vulnerable, but feels he must change that now.
  • “The hardest thing so far has been trying not to be a prick because that’s normally kind of what I’ll do in the first stages of dating is kind of be a slight jerk, you know, so that they…I don’t know…” (D, 04:03)

Relationship Patterns and Self-Reflection

• Changing Tactics:

  • Blake explores being more genuine versus playing the “player” or aloof role, admitting old habits are hard to break.
  • “Is being nicer more natural? Or have you been doing the player thing, act like a jerk for so long, that becomes more natural?” (B, 04:38)
  • “Yes. Yes. I would say I should be all the way. Yeah.” (D, 04:45)

• Dating “Good Girls”:

  • He recalls a previous attempt at a more traditional, exclusive relationship, which ended poorly after pressure to define the relationship.
  • “It was a whole explosion at Thanksgiving. I had to go and have Thanksgiving with her parents, and it was weird and creepy and then wanted me to, like, she wanted me to commit and not even commit hardcore just to say that we were a couple and that I wasn’t going to go out looking for other women.” (D, 05:47)
  • He values honesty, but also resists labels and exclusivity, which he acknowledges is a “hot topic and a really scary topic” for many men.

Societal Expectations and Gender Dynamics

• When to Define the Relationship:

  • The hosts and Blake agree that labeling is expected around two to three months in, but it can still feel fraught.
  • “That’s appropriate labeling time, right?” (A, 07:07)
  • “Yeah, it is for a girl, I think. Yeah. I mean, there’s going to be some expectation, I think, of having a definition, you know.” (C, 07:10)

• Why Commitment Is Scary:

  • Kristin and Abby offer a female perspective about why women want clarity, while Blake admits men can feel anxious about commitment, sometimes indefinitely.
  • “...we were just defending her stance, but I think women need to understand that commitment for guys is a really hot topic and a really scary topic.” (C, 08:23)
  • “I do know some guys out there that any sort of commitment, even. Even in naming or a label, is considered commit.” (A, 08:46)

Listener Engagement and Future Episodes

• Advice Column Plans:
  • There’s a discussion about Blake responding to female listeners’ emailed questions about relationships in Atlanta on future episodes.
  • “A lot of the questions coming in are from girls in Atlanta that are saying, you know, my guys, he’s not willing to commit. I mean, people that have been dating for a year, year and a half, they still…the girl still feels like he’s not ready to go into this relationship 100%.” (D, 08:51)
  • Blake is encouraged to share his responses live: “Pick out some of the more interesting of those emails…we’ll read lines from the emails and have you address those questions.” (A, 09:35)

Notable Quotes & Memorable Moments

• On dating with family stakes:
  • “You can’t really just do what normally works when you’re worried about offending family, really.” (D, 02:32)
• On breaking habitual dating behaviors:
  • “It is kind of nice being able to have that freedom to just, you know, treat them the way…I think just naturally would do it. But it is throwing me off my game a little bit, for sure.” (D, 05:02)
• On why commitment can be a big hurdle:
  • “Commitment for guys is a really hot topic and a really scary topic.” (C, 08:23)

Important Timestamps

• 00:03 – Introduction to Blake and explanation of his anonymity
• 01:18 – Details on new romance with “Diana” and holiday trip
• 02:58 – Why dating Diana is tricky due to family connections
• 04:03-05:23 – Blake explains his usual dating “game” and how he’s trying to change it
• 05:47 – Story about dating a “good girl” and the fallout from refusing labels
• 07:07 – Hosts discuss appropriate timing to define a relationship
• 08:23 – Gender differences about commitment and relationship definition
• 08:51 – Blake references listener questions for future advice segments

Episode Tone and Style

True to The Bert Show’s style, the conversation is humorous, self-deprecating, and candid, with a natural rapport between the hosts and guest. Blake’s vulnerability as he discusses his patterns and anxieties gives listeners honest insight into dating from a male perspective, while the hosts both challenge and empathize with him—balancing real talk with light-hearted teasing.

Takeaways for Listeners

• Family dynamics can raise the stakes in early dating and intensify anxiety about getting things right.
• Men may default to defensive or “player” behaviors out of fear or habit, especially when commitment looms.
• Women’s desire for relationship clarity is often matched by men’s apprehension about labels or exclusivity.
• Open conversation can help bridge the gender gap in expectations, and Blake’s willingness to answer real-life questions promises ongoing insights in future episodes.

For more from “Blake,” read his blog at allthehitsq100.com and watch for upcoming listener Q&A segments on the show!