The Bert Show Podcast – "Vault: He Wants To Shoot His Shot With His Friend"
Date: January 9, 2026
Host: The Bert Show Cast (Bert, Melissa, Jeff, Jennifer, Tamara)
Theme:
A deep dive into the emotional complexity of wanting to transition from a long-term friendship to a romantic relationship—a listener, Pete, calls in seeking advice about confessing his love to a close female friend.

Episode Overview

In this episode, The Bert Show team helps a listener, Pete, navigate the emotional minefield of being "in love with his best friend." Pete has spent several years as a confidante and supporter for this woman, after a brief romantic connection years ago. With her newly single, Pete wonders whether he should finally confess his enduring feelings, risking both rejection and the end of their friendship. The hosts and callers provide a mixture of empathy, humor, and real talk—debating whether Pete should go for it or keep his feelings to himself.

Key Discussion Points

Pete's Situation: The "Friend Zone" and Unspoken Love

[01:39–04:54]

• Pete's History: Best friends for five years; had a brief romantic phase that didn't work out. Pete had previously confessed his feelings, but the relationship didn't advance. Since then, he’s been “waiting in the weeds.”
  • Quote:
    Host (Birch): “You have fallen in love with this girl and basically she's not looking at you the same way?”
    Pete: “Uh, yeah.” [02:16]
• Pete’s Dilemma: The woman recently exited a long-term relationship. Pete struggles with being around her platonically when his feelings haven’t faded.

Redefining Friendship: Are Pete's Feelings Mutual or Is He Being Used?

[05:50–09:12]

• Reconnection Moment: Pete and his friend drifted apart after he wrote her a heartfelt letter. Months later, she reached out to him, referencing the letter—but she was still with her boyfriend.
• Perceptions from Hosts:
  • Jennifer suggests Pete is acting as a "doormat" and that the friend might be aware of his feelings but maintains the friendship for her own benefit.
    • Quote:
      Jennifer: “It sounds like you've been a doormat for too long. It sounds like to me that she is taking advantage of this friendship a little bit.” [07:12]
  • Melissa counters that the woman may simply value Pete’s friendship without ill intent.

The Reality of Unrequited Emotions

[09:12–12:24]

• Responsibility and Communication: Discussion about whether the friend has a responsibility to be upfront if she knows Pete's true feelings.
• Painful Honesty: Melissa insists Pete must be honest, as the friendship is “not balanced”—and advises that Pete should confess and be prepared to walk away if the feelings aren’t returned.
  • Quote:
    Melissa: “You are in love with her. She's not in love with you. And you have to be honest with her...if you're just honest with her, tell her how you feel, and she doesn't respond, then you're gonna have to leave because it's only hurting you.” [09:28]

Listener Callers Share Their Stories and Advice

[10:20–15:19]

• Tamara: Shares a cautionary tale—she told her best friend she loved him, but the confession “freaked him out” and ended their communication.
  • Quote:
    Tamara: “I decided to tell him...it freaked him out. And I haven't heard from him since then.” [11:10]
  • Advice: “Hell no”—don't risk it. [11:20]
• Other Callers:
  • John: Suggests considering whether losing the friendship is worth the confession.
  • Another Tamara: Shares a story with a happy ending—after discussing feelings, she is now engaged to her best friend.
    • Quote:
      Tamara: “If we hadn't ever talked about it, we would have always had that question and wondered what would have happened.” [14:44]

Hosts’ Reflections: Is the Friendship Already Over?

[12:24–15:19]

• Melissa: Argues the friendship is “already done” in Pete's heart—real friendship is impossible with unreciprocated romantic feelings.
• Jennifer: Asserts the woman already knows how Pete feels:
  • Quote:
    Jennifer: “A guy who's in love with you looks at you differently...she knows it. I don't think he even has to say anything to her. She knows already, and I think she's taken advantage of it.” [12:37]
• Host (Birch): Points out the emotional toll on men who wait in hope:
  • Quote:
    Host (Birch): “When you play that way and she believes that you really are the friend...it's slowly just crushing you.” [13:43]

Gender Perspectives: Why Do Some Men Wait Forever?

[15:19–17:19]

• Jeff: Suggests the patience is less romantic and more about hope for intimacy:
  • Quote:
    Jeff: “Guys will stand around forever if there's a chance at sex.” [15:32]
• Humor and Sarcasm: Jeff jokes about the delusional hopefulness of men in Pete's position—“every minute [he] is with her, there's the chance that that could be the night that they make out.” [15:57]

Should Pete Confess Now or Wait?

[17:20–21:28]

• Advice Roundtable: Each host offers personal advice in the style of a “best friend”:
  • Jeff: Believes advice is pointless—Pete will keep hoping no matter what.
  • Jennifer: Advocates for honesty but warns that nothing will be the same afterward.
  • Melissa: Advises Pete to have a private conversation, but to wait until the friend is emotionally ready (i.e., after more time post-breakup).
  • Host (Birch): Agrees with Melissa—advises more patience before making the confession, as the friend is “emotionally spent” after her breakup.
    • Quote:
      Host (Birch): “I would say have the talk to her, but you gotta hold out for a couple of more months...she's gonna go through this period of, I don't want anything to do with guys at all.” [19:21]
• Worst-case Scenarios (with humor): Jokes about making a creepy shrine of her photos, referencing pop culture (Lionel Richie’s "Hello" video), and the absurdity of certain movie tropes.

Notable Quotes & Memorable Exchanges

• Jennifer on being used:
  “It sounds like you've been a doormat for too long...she is taking advantage of this friendship.” [07:12]

• Melissa on the pain of unrequited love:
  “You are in love with her. She's not in love with you...you have to be honest with her.” [09:28]

• Host (Birch) on friendship after romantic feelings:
  “You can't go back to just being friends...it’s done for him.” [12:24]

• Jeff’s cynical take:
  “Guys will stand around forever if there's a chance at sex.” [15:32]

• Jennifer on transparency:
  “She knows he's on a different level than just a guy friend.” [08:54]

• Tamara’s warning from personal experience:
  “I decided to tell him...it freaked him out. And I haven't heard from him since then.” [11:10]

• Tamara (different caller) on a happy ending:
  “If we hadn't ever talked about it, we would have always had that question.” [14:44]

• Melissa on Pete’s next step:
  “Be honest with her, but...have the conversation to her. I think you should...explain to her how you feel and how you’re acting.” [19:05]

• Host (Birch) on waiting for the right moment:
  “Hold out for a couple of more months...she's gonna go through this period of, I don't want anything to do with guys at all.” [19:21]

Takeaways & Final Thoughts

• Emotional Honesty is Crucial: Most hosts agree that Pete needs to be honest, but with clear expectations.
• Timing Matters: Advice leans toward waiting until the friend is more emotionally available.
• The Friendship’s Fate: The panel agrees—once deep romantic feelings exist, it's nearly impossible to return to pure friendship.
• The Pain of Unrequited Love: Pete’s situation resonates with listeners, many of whom have been there—torn between preserving a friendship and risking it all for love.
• Humor as a Coping Mechanism: The Bert Show lightens the mood with humor, preventing the conversation from becoming too heavy.

Important Timestamps

• [01:39–04:54]: Pete shares his history with his best friend
• [07:12]: Jennifer calls out the dynamic as Pete being a doormat
• [09:28]: Melissa urges Pete to confess and prepare to move on
• [11:10]: Tamara’s cautionary tale about confessing love
• [14:44]: A listener’s success story—engaged to their best friend
• [19:05]: Group offers final advice for Pete’s “big talk”

Summary in One Line:
The Bert Show guides Pete through the hazards and hopes of confessing long-held love to a best friend—blending real talk, humor, and heartfelt advice for anyone stuck in the friend zone.