Podcast Summary: The Bert Show – "Vault: She's Playing Two Guys at Once and Needs Our Help"

Original Air Date: March 20, 2026

Episode Overview

This episode of The Bert Show digs into a familiar, modern dating dilemma: a listener, a single 26-year-old woman in Atlanta, seeks advice on how to gracefully juggle two men—especially with Valentine’s Day looming. The Bert Show crew and callers weigh in with humorous, candid, and occasionally conflicting perspectives on honesty, logistics, and the gender dynamics at play.

Key Discussion Points & Insights

The Listener's Email (01:00)

• Situation: The listener is dating two polar opposite men. She hasn’t misled them about exclusivity, but suspects each believes he’s the only one. With Valentine’s Day on a Saturday and both vying for plans, she’s in a bind—already committed to dinner with one but lately more interested in the other.
• Dilemma: How to manage Valentine’s without lying or breaking things off—does she see both, and how does she explain herself?

Panel’s Immediate Reactions

• Juggling Both Dates (02:35):
  • Male panelists muse about squeezing both dates into the same day (e.g., dinner with one, late night with the other). Consensus: On Valentine’s, dinner is essentially a full-night commitment, making this difficult.
• Intimacy and Commitment:
  • They reflect on whether she has gotten intimate with either—suggesting the answer might dictate how easily she can pivot between the men.
  • Quote:
    "If she's committed to one for dinner, which is what I think her email said, guy number one is getting dinner, but guy number two she likes more." (03:02, Male Panelist 2)

Honesty vs. Strategy (04:41)

• Host 2 on honesty:
  "Honesty in this case is great. If we know that a woman is dating me and dating somebody else, it makes you the hotter commodity. The chase is what we need." (04:41, Host 2)
• Men are more competitive if they know there’s another contender. The suggestion: don’t lie—tell guy #2 she already has plans, and he’ll work harder.

Alternative Solutions

• Friday Night Solution: (05:16)

  • Several panelists and callers suggest celebrating “Valentine’s” with one guy on Friday, keeping Saturday for the other. This allows her to maintain honesty and avoid overlap.
  • Caller anecdote:
    "Valentine's the night before, I spent the night with one girl, woke up and made breakfast for that morning and went out and had lunch that day and then went out that night with another girl, ended up getting married to the girl that I went out the first night with." (05:46, Caller 3)

• Panelist Endorsement:
  "It's actually would work to her advantage if she actually blows off the one she likes more on Valentine's night. If she does it properly... He's gonna work so much harder because you just made him second." (05:16, Host 1)

Creative Excuses and Caller Input

• Caller Ideas:

  • Spend Friday with the man she wants most, then regroup and enjoy dinner with the other Saturday night. “If I can accomplish this across state lines, I’m sure she can accomplish it in one.” (06:25, Caller 2)
  • Tell one you’re “spending Valentine’s with your mom”—panel is amused but notes this is classic guy move, and the listener wants to avoid lying. (07:02, Caller 4)
  • Host Commentary:
    "If you're dating a girl who chooses to spend Valentine's Day with her mom, get out of the relationship, she is crazy." (07:40, Host 1)

• Wing-woman Strategy:
  Go to a girls’ event like Bitterball, say you’re helping a lonely friend, then go out with one guy Friday and one on Sunday. (08:08, Caller 1)

Bottom Line: Panel Advice (08:28–10:09)

• Unanimous Advice: Stay honest, be clear you’re booked Saturday, and see the other guy Friday.

• Host 2:
  "There's no reason to be dishonest. Tell him that you've already got something lined up for Valentine's night, and ... he'll make Friday night way better." (08:55, Host 2)

• Panelist humor about men and women’s thinking:
  "Way better. And it is physically impossible for a woman to dumb it down to a guy's level. You guys are incapable." (09:07, Host 1)

• Final Consideration: Panelist quips — just choose by asking, "Who do I want to wear the prettiest lingerie for?" (09:59, Male Panelist 2)

Notable Quotes & Memorable Moments

• Host 2 (04:41):
  "The chase is what we need."
• Host 1 (05:16):
  "It’s actually would work to her advantage if she actually blows off the one she likes more on Valentine’s night."
• Caller 3 (06:01):
  "Ended up getting married to the girl that I went out the first night with."
• Caller 2 (06:25):
  "If I can accomplish this across state lines, I’m sure she can accomplish it in one."
• Host 1 (07:40):
  "If you're dating a girl who chooses to spend Valentine's day with her mom, get out of the relationship, she is crazy."
• Host 1 (09:07):
  "It is physically impossible for a woman to dumb it down to a guy's level. You guys are incapable."
• Male Panelist 2 (09:59):
  "All she has to ask herself is, who do I want to wear the prettiest lingerie for? And then she has her answer."

Timestamps for Key Segments

• 01:00 – Letter from listener: juggling two guys on Valentine’s Day
• 02:35 – Initial panel responses, logistics of double-dipping
• 04:41 – Panel and host agree: honesty is the best policy
• 05:16 – Strategic suggestion: give the more-desired guy the “exclusive” Friday night
• 06:01–06:59 – Callers share firsthand stories & advice
• 07:40 – Panel jokes about “Valentine’s with mom” excuse
• 08:28–10:09 – Panel consensus: stay honest, work the schedule, don’t overthink it

Conclusion

With humor, candor, and plenty of real-life anecdotes, The Bert Show panel encourages honesty and smart scheduling. Their advice: don’t lie—if you’re dating two guys, be up front and use the calendar to your advantage. And above all, don’t stress: if Friday night is good enough for one, the other will rise to compete. As always, laughter, good-spirited jabs, and a dash of cheeky wisdom make the episode both insightful and entertaining for anyone navigating modern dating’s trickier scenarios.