The Bert Show: Vault Episode – Dating Dictionary

Release Date: November 19, 2025
Main Theme:
This episode of The Bert Show dives deep into the ever-confusing language of modern dating, using real listener input to define and debate some of the most ambiguously used terms in relationships and dating culture. The panel discusses the nuances of phrases like “hooking up,” “seeing each other,” and especially “best guy friend,” aiming to crowdsource a practical “dating dictionary” for listeners navigating today’s romantic landscape.

Key Discussion Points & Insights

1. The Need for a Dating Dictionary

• Timestamps: 01:33–02:26
• The hosts open by commenting on the confusion caused by differing definitions for common dating terms, particularly when people from varied backgrounds interact.
• Notable Quote:
  • "The definitions for dating terms can be different. Hooking up is the classic example." — Birch (Host) [01:48]

2. Previously Defined Terms

• Timestamps: 02:26–03:23
• The show recaps definitions already established through listener feedback:
  • Hooking up: Just making out (not sex).
  • Seeing each other: Pre-exclusive stage, not officially dating.
  • Dating: Also pre-exclusive.
  • In a relationship: Exclusive.
  • The bases:
    • First: Kissing/making out
    • Second: Above the border (over-the-shirt action)
    • Third: Below the border
    • Home run: Sex
  • On a break: Trial separation where making out is allowed but sex is not.
• "We started our Bert Show Dating Dictionary, 'hooking up' is the first term, and that is defined now... as just making out." — Co-host/Panelist 2 [02:08]

3. Today's Focus: “Best Guy Friend”

• Timestamps: 03:29–07:01
• Several options for discussion arise, but the panel lands on “best guy friend” as the most contentious and ambiguous term.
• The initial debate focuses on whether a “best guy friend” is always non-threatening (e.g., gay best friends like Will & Grace) or if it’s more complicated, especially concerning past romantic involvement.
• The co-hosts raise concerns about what it means for current romantic partners.
• "I think a guy would have a problem with a girl having a best guy friend." — Co-host/Panelist 3 [04:02]

4. Listener Stories: Unpacking “Best Guy Friend”

• Timestamps: 05:15–10:57
• Caller 1 (Jessica) [05:20]: Shares that her "best guy friend" is her ex, whom she keeps around as a potential backup if her current relationship ends.
  • "My best guy friend is a guy that I previously dated and had sex with who is my backup in case I ever break up with my current boyfriend." — Caller 1 [05:22]
  • The co-hosts react, noting this isn’t a purely platonic relationship and liken it to “friends with benefits on standby.”
• Caller 2 [07:54]: Describes her “best guy friends” as men she found fun but not attractive or appealing enough to date or sleep with. She stopped hanging out with male friends after getting married to avoid “bad optics.”
  • “It’s hard to have a husband and hang out with your guy friends because that kind of looks bad to your husband.” — Caller 2 [08:53]
• Jen Fallon Segment [09:08]: The panel interviews Jen Fallon about her own best guy friend. She admits her current best guy friend is an ex, but her previous was purely platonic due to lack of attraction.
  • "...before I met this guy, was my best guy friend from high school. Never ever dated him. Never thought of kissing him. Was disgusted by the thought..." — Jen Fallon [09:26]
• Caller 3 (Rachel) [10:28]: Shares that her best guy friend is an ex she dated years ago. None of her subsequent partners like him, and vice versa, but they’re genuinely platonic now.

5. Gender Dynamics & Jealousy

• Timestamps: 11:00–11:47
• The panel circles back to relationship anxieties associated with having a “best guy friend,” arguing men typically do not like their girlfriends to have a close male friend, especially if there’s a romantic or sexual history.
• "If you're in a relationship with a girl, you don't want her to have a best guy friend, because generally that means at one point or another, they have hooked up." — Birch (Host) [11:07]

6. Male Perspective – Are Men “Hanging Around” Hoping?

• Timestamps: 11:47–12:11
• The show speculates that men who are “best guy friends” often hope for more than friendship, with one host suggesting, “if he's hanging out...he’s hoping he’s going to crack in.”
• "If you're calling him your best guy friend, then he wants to have sex with you." — Co-host/Panelist 3 [11:32]

7. A Male Caller’s Perspective

• Timestamps: 12:17–13:07
• Caller 4 (James) calls in with a unique situation—his ex-wife is his best friend and part of his wider blended family, despite the complicated history.
  • Highlights shifting definitions and personal boundaries for what constitutes a “best friend” post-romance.

8. Conclusions and Lingering Confusion

• Timestamps: 13:28–14:10
• Hosts attempt a dictionary definition: “Best guy friend” is generally somebody you have already hooked up with but are now platonic with—or, at a minimum, someone with past romantic involvement.
• They note an exception: platonic friends without history—but agree this is less common.
• "...the one constant is that you guys hooked up at one point or another. So there has to be another term...for the person that you’ve never hooked up with before, that is still considered a really good friend." — Birch (Host) [13:55]

Notable Quotes & Memorable Moments

• On Defining 'Hooking Up':
  • “Hooking up is the first one we put on our dating dictionary... defined as just making out.”
    — Co-host/Panelist 2 [02:08]
• On Best Guy Friends as 'Backups':
  • “He knows that I have a best guy friend, but he doesn’t know the history.”
    — Caller 1 [05:59]
• On Platonic Friendships vs. Attraction:
  • "He was just the guy that had all girlfriends. Like he was just..."
    — Jen Fallon [09:38]
• On Jealousy & Boundaries:
  • "I would hate that. I would hate that. I don't know why I would hate it. I would just hate it."
    — Birch (Host), about his partner having a “best guy friend” [12:06]

Key Timestamps for Segment Reference

• 01:33–02:26: Introduction to dating dictionary concept
• 02:26–03:23: Recap of previously defined terms
• 03:29–07:01: Debate over “best guy friend”; first caller
• 07:54–10:57: More caller stories and Jen Fallon’s input
• 11:07–12:11: Discussion of jealousy and gendered double standards
• 12:17–13:07: Male caller’s unique family dynamic
• 13:28–14:10: Hosts’ attempt at a final definition

Overall Takeaway

The episode is a lively, candid exploration of how language shapes expectation and trust in dating. The panel’s crowd-sourced definitions expose the implicit anxieties and ambiguities around male-female friendships—especially when there’s past romance involved. Ultimately, the episode can’t unearth a consensus, but it succeeds in airing the range of perspectives both listeners and co-hosts bring to an ever-evolving dating dictionary.