The Bert Show – Episode Summary

Episode Title: Vault: He Hooked Up With Four Women In The Wedding Party...Now What?

Release Date: December 12, 2025

Cast: Bert, Kristin, Abby, Cassie, Tommy, Jamie, Crash, Knox, Callers, "Ryan"

Main Theme & Purpose

This episode focuses on outrageous dating drama as the segment delves into a sticky situation: "Ryan," a friend of the show, is headed to a wedding where he’s previously hooked up with four of the women who’ll be in attendance – and none of the women know about each other. The hosts debate how Ryan should handle the weekend, riff on the friction and tension likely to arise, and invite listeners to weigh in with their advice, banter, and first-hand stories.

Tone: Playful, cheeky, and full of good-natured ribbing.

Key Discussion Points & Insights

1. Setting the Scene: Ryan’s Predicament

• [01:37] The hosts introduce Ryan's situation:
  • Ryan is attending a wedding (not clear if he’s in or just attending) where four women he’s hooked up with—none knowing about the others—will also be guests.
  • He maintains cordial, possibly flirtatious relationships with all of them—“the door is always open.”
• The dilemma: Should Ryan bring a date to avoid drama, or go stag and risk things blowing up?

Key Quote

“Should he bring a date and make them all jealous? Should he go stag and fend them all off all weekend, have it be a big competition?”
— Co-host (Jamie), [01:55]

2. Listener and Co-host Reactions

• [02:43] Caller Tammy raises skepticism about Ryan’s perceived chances, but Jamie insists:

“I know these four women. He can.”
— Jamie, [02:52]

• The "wedding hookup" myth is debated. The hosts joke about the atmosphere leading to more romantic encounters.
• Another caller, Mike, amps up the expectations for Ryan:

“This guy needs to hook up with at least two of them. And Crash could back me up on this. One of them should be outside of those four.”
— Mike (Caller), [03:31]

• The team notes reality—some of the women might have dates of their own.

3. Ryan Joins the Conversation

• [04:31] Ryan himself calls in, sounding bemused.
  • He jokes about bailing with a fake illness.
  • Shares the breakdown: “Two [relationships] long term, two hookups.” ([05:11])
    • Clarifies “long term”—several months for two, a couple days for the others.
  • Ryan’s main concern isn’t about adding notches, but managing the drama:

“I just don’t want anybody…I’d rather bring a date and just keep everybody else at bay because…I don’t want anybody to get their feelings hurt.”
— Ryan, [05:50]

• The hosts tease his “sensitive” side.

4. Predictions and Catastrophe Scenarios

• [06:21] Host:

“So the goal this weekend really is okay, yeah, hook up. But B, make sure that, no, there’s no bad feelings between all the women.”
— Host, [06:21]

• Ryan: “I don’t think I’m coming out of this weekend one way or the other without at least the three…finding out about each other. I just don’t want it to be a big deal.” [07:23]
• Callers warn that bringing a date might cause the women to compare notes and “the fur [will be] flying.”
• Crash (co-host) lays out a challenge:

“I would like you to come back from this wedding hooking up with one of the four, the maid of honor, and the bride and the groom.”
— Crash, [07:43]

5. Unexpected Female Callers Throw Themselves In

• [08:02] Lisa, a caller, offers to be Ryan’s date:

“I’m available for a date if you need one.”
— Lisa (Caller), [08:02]

• Another caller, Trina, also puts herself up as a tall single woman ready for the role ([08:46]):

“So if you like tall women, let me know.”

• The hosts marvel at women’s willingness to jump into the drama and joke about “Ryan’s” appeal.

6. A Real-Life Parallel & Gender Dynamics

• Amy (Caller) recounts being at a wedding with her husband and all four of his former hookups—leading to awkwardness and territorial feelings. Her strategy:

“So I just sat in his lap…are they sitting there thinking, ‘I’ve had your man’ or what?”
— Amy (Caller), [11:09]

• The hosts riff on the social dynamics, blaming “mothers raising us to be good boys” yet girls want the “bad boy.”
• Ryan defends himself as “a good, respectful person—just to four different women.” [09:28]

7. Final Strategies and Movie Analogies

• Wedding is a few months away—gives Ryan time to plan.

“If I bring the same girl to that one that I bring to this one, I can probably circumvent some of the drama.”
— Ryan, [09:46]

• The hosts compare the whole scenario to a high school movie or a Hollywood rom-com (“Four Weddings and a Funeral” style).

Memorable Quotes & Notable Moments

• “Crash could back me up on this. One of them should be outside of those four.”— Mike (Caller), [03:34]
• “I’m just worried about getting slapped or punched or a drink thrown in my face or something along those lines.”— Ryan, [05:50]
• “If this dude takes a date, we all know how catty women are. They’re gonna get talking amongst each other and then there’s gonna be fur flying.”— Stephanie (Caller), [06:49]
• “I don’t think I’m coming out of this weekend clean anyway… I just don’t want it to be a big deal.”— Ryan, [07:23]
• “I’m available for a date if you need one.”— Lisa (Caller), [08:02]
• “Are they sitting there thinking, ‘I’ve had your man’ or what?”— Amy (Caller), [11:17]
• “I’m a good, respectful person. I just happened to have run into a weekend where I was a good, respectful person to four different women.”— Ryan, [09:28]

Important Timestamps

• [01:37] – Main scenario introduced
• [02:43] – Listener call-in: skepticism and incredulity
• [03:31] – Listener “Mike” raises the stakes for Ryan
• [04:31] – Ryan joins the show
• [05:11] – Relationship breakdown: “two long term, two hookups”
• [05:50] – Ryan’s real fear: drama, not sex
• [06:49] – Female caller warns about female dynamics at weddings
• [07:23] – Ryan predicts the doom
• [08:02] – Lisa volunteers as a date for Ryan
• [11:09] – Amy shares a parallel experience
• [09:46] – Ryan proposes a strategic repeat date

Conclusion & Flow

The episode weaves between playful roasting, dating advice, and wild listener stories, providing both entertainment and an odd sense of camaraderie. The cast and callers dig into the comedic potential of Ryan’s challenges, explore social stereotypes, and affirm that wedding weekends are fertile ground for drama.

Above all, the episode remains fun, irreverent, and listener-focused—a relatable “what would you do?” scenario played for maximum laughs and lighthearted self-reflection.