Podcast Summary: The Bert Show – “Vault: She Wants To Celebrate Her Anniversary With Multiple Guys?!”

Date: January 28, 2026
Podcast: The Bert Show (Pionaire Podcasting)
Episode Theme:
A listener, Lena, calls in to share her unconventional plan to mark the one-year anniversary of a breakup by organizing four dates in one weekend. The show dives into dating rebounds, confidence, and the modern world of dating — with humor, real talk, and anecdotes from the Bert Show cast.

1. Episode Overview

The main theme of this episode is reclaiming personal happiness and confidence after heartbreak. Lena, having spent nearly a year moping after a three-year relationship, decides to “celebrate” the breakup anniversary by jumping back into dating — lining up four dates for one weekend. The Bert Show’s hosts dissect her plan, share insights about dating culture, and enthusiastically follow up to see how Lena’s dating “marathon” went.

2. Key Discussion Points & Insights

Lena’s Background and Motivation

• Context: Lena broke up with her boyfriend of three years almost a year ago and has been struggling to move on, particularly around Valentine’s Day (00:09).
• Breakup Anniversary: Instead of mourning the milestone, she decided to take proactive steps to move forward:
  “Forget this. I’m not going to mope about this guy anymore. It’s over. I’m getting back out there and I have… four dates lined up for this weekend.” (00:22, Lena)

The “Four Date Marathon” Plan

• Intention: The hosts clarify that Lena intentionally scheduled four dates as a bold way to “bust the slump” and force herself into the dating pool (00:46-01:09).
• First Dates Since Breakup: These are Lena’s first real dates in almost a year.

The Hosts’ Take: The Slump Buster

• Hosts encourage Lena’s strategy:
  “If you’re gonna come out of this thing, come out of it strong man. Four days.” (01:04, Host A)
• Risk and Reward: They discuss the pros and cons, joking about the potential for rapid discouragement or success, given the intensity (01:14-01:36).

Date-by-Date Recap (02:09–06:12)

1. Thursday: The Group Coworker Date
   • Very casual, treated more as a group hangout than a real date.
   • “It was cool that it was like no pressure and we didn’t really hit it off, so it was fine. And so it was kind of like we can act like we didn’t even go on a date.” (02:47, Lena)
2. Friday: The Real Winner
   • Traditional dinner and drinks, lasting till after 3 a.m.
   • Good chemistry; ended with a kiss.
   • “I really like this guy. Like, this guy wins. He’s the only one I’m going out with again.” (04:45, Lena)
3. Saturday: The High School Throwback
   • Dinner and a movie, but feeling was awkward — no chemistry.
   • “It was just… the conversation was boring. I felt like I was kind of on an interview… no chemistry.” (05:00, Lena)
4. Sunday: The Canceled Date and a Callback
   • Lena, exhausted by Saturday’s bad date, cancels on the fourth guy and spends another day with “Friday Guy”, even seeing the same movie as Saturday.
   • “We spent all of Sunday together… I just kind of—I’m not gonna tell him [I saw the same movie].” (05:53, Lena)

The Hosts’ Commentary: Dating Strategy & Confidence

• Shorter Dates, More Check-Ins:
  Host A jokes about a universal “30-minute contract” in dating to save time if the spark isn’t there (03:22; 05:18).
• Concept of Safety and Support:
  The first group date is viewed as a wise “safety net” (04:22).
• Confession vs. Openness:
  Lena is not sure about telling “Friday Guy” how many dates she went on that weekend — the hosts affirm it could be off-putting if the number is too high (06:23).
• The Power of Confidence:
  The hosts agree Lena’s confidence, gained from knowing she had options, made her more attractive and successful:
  “It could have been the confidence that she brought, you know, with having four dates lined up… that confidence that made it so great with Friday Guy.” (07:09, Host E)
  “I had a whole bunch of dates lined up, and here it made me more confident because if Thursday didn’t work out, I had Friday lined up.” (07:53, Host A)

Societal Double Standard? (08:29–09:05)

• The hosts debate whether a man doing the same thing would be judged differently, with some agreeing the context matters (e.g. post-breakup, intentions).
• Humorous Boob Math:
  “That’s eight boobs. Boob math. It always comes down to boob math for us.” (09:05, Host A)

3. Notable Quotes & Memorable Moments

• Lena, on her motivation:
  “Valentine’s Day was just, I guess when I hit bottom. And now I’m like, you know what? Forget this. I’m not going to mope about this guy anymore.” (00:22)
• On the Friday guy:
  “He’s the only one I’m going out with again.” (04:55)
• Host A, wishing for more honest early check-ins:
  “If we could just check in with each other on 30 minute increments on dates and each has the right to say, this is either going great or… you walk away with no social repercussion.” (03:31)
• On double standards:
  “Does it have the same texture? Or would you guys be all over him going, ah, stop being a whore. You have four women lined up in four days.” (08:29, Host A)

4. Key Timestamps

• 00:09–00:22: Lena explains the breakup anniversary and her plan for four dates.
• 01:04–01:36: Hosts analyze the potential outcomes of Lena’s approach.
• 02:09–03:15: Lena details her first group “coworker” date.
• 04:28–05:18: Recap of Friday (the standout date) and Saturday (the flop).
• 05:53–06:23: The Sunday “date swap” and concerns about revealing too much to Friday Guy.
• 07:09–07:53: The hosts discuss how confidence shaped Lena’s experience.
• 08:29–09:05: Exchange on gender expectations and “boob math.”

5. Takeaways

• Throwing yourself back into dating after heartbreak can boost confidence—especially with multiple options.
• The order or number of dates doesn’t matter as much as the personal growth gained from putting yourself out there.
• Honesty and self-awareness are key, but sometimes a little discretion is wise.
• Traditional dating rules are ripe for creative, self-empowering twists — with a healthy dose of humor.
• Gender double standards persist, but context and intention do matter.

Memorable Moment:
Friday Guy “wins” Lena’s heart — reminding listeners that sometimes, you need several chances to get that one great match. The journey, and the laughs, are just as important as the outcome.

Hosts present: Bert (Host A), Kristin, Abby, Cassie, Tommy, and the whole Bert Show cast.
Listener involved: Lena