The Bert Show: Vault – Phil Tries Men's Magazine Test To Pick Up Women

Original Air Date: November 7, 2025
Hosts & Cast: Phil Serena, Melissa, Producer Tracy, and others
Episode Theme: Testing Men's Magazine Pick-Up Advice In Real Life

Episode Overview

In this episode, the Bert Show casts a humorous and honest lens on dating advice from men’s magazines. Team member Phil Serena is tasked with following a series of “pick-up” instructions from AskMen.com to see if he can successfully separate a woman from her group (her "flock") at a bar and get her number. The show is equal parts comedic storytelling, awkward social experiment, and candid debrief about what really happens when men try these so-called foolproof tips.

Key Discussion Points & Insights

1. Phil’s Vacation (01:00 – 04:54)

• Phil recounts his recent all-inclusive vacation in Mexico, including mishaps and misunderstandings:
  • Phil on All-Inclusive Resorts: “We got our money back in airfare and hotel alone. I think I drank my weight in piña coladas and rum all weekend.” (01:23)
  • A tattoo of the University of Georgia’s “circle G” led Mexican locals to think Phil was gay:
    • “She goes, ‘Oh, to novio.’ And I said, ‘No, no novio.’… Apparently when Latin and Spanish men would go out… they would paint on a G on their shoulder.” (04:00 – 04:29)
    • Phil’s confusion and comedic reaction to being misunderstood is a recurring theme.
  • The hosts riff on Phil’s inability to “hook up with women” both abroad and back home.

2. The Men’s Magazine Challenge: The Set-Up (04:54 – 06:30)

• Premise: Phil is to try out pick-up techniques from AskMen.com at Atlanta bars and clubs.
  • The main “challenge”: Approach a group of women (the “herd” or “flock”), identify one he's interested in, separate her from the group, and attempt to get her number.
  • On Group Dynamics:
    • "As a guy, like your biggest fear and biggest challenge… to approach a group of women…" (05:18)
    • “You just follow these rules, no worries.” (05:57)

3. The “Rules” According to AskMen.com (06:30 – 08:26)

• Phil explains the steps:
  • Notice the drink your target is having, buy her that drink (either send it over or bring it yourself).
  • Casually charm the entire group: “Hey, how you doing, everybody?”
  • Ask the “mother hen” for approval.
  • Break off into private conversation with the target, try to get her number.
• The hosts joke about terminology (“herd”, “flock”, “gaggle”), poking fun at the advice and each other.
• Key Insight: “Confidence. Confidence. Confidence. That is all it takes.” – Phil (08:26)

4. The Field Test: Phil Tries the Rules (08:56 – 14:55)

• Attempt 1: The Drink Delivery (10:45 – 12:37)

  • Phil approaches woman, offers drink, tries for her number.
  • Rejection: She claims her (female) friend is “taking care of her,” suggesting lesbian relationship—hosts debate if this was a truthful answer or just a brush-off.
  • Quote:
    • Club Woman: “I'm very flattered, but my girlfriend over there is going to take me home tonight.” (11:09)
    • Phil reflects: “So in my mind, I'm like, okay, she's lesbian. Fine, no big deal. No… My pride, my–she must be a lesbian. She don't want none of me.” (12:37)

• Attempt 2: The Recently Single Excuse (13:23 – 13:57)

  • Phil tries again; this time the woman claims she just got out of a relationship and isn’t interested.
  • Quote: Club Woman: “I’m sorry, you can’t get my number right now. I’m just getting out of a relationship, and I’m out with my friends… not really out for that.” (13:41)

• Attempt 3: Raw Persistence (“Caveman” Approach) (14:17 – 15:00)

  • Phil, abandoning the rules, pulls a woman directly from her group (no drink strategy).
  • She says she has a boyfriend (and his brother is present).
  • Quote:
    • Club Woman: “Yeah, I’m getting in trouble just talking to you right now. So there’s nothing.” (14:53)
  • Phil sums up: “Ouch. Dude, you make me so uncomfortable.” (15:00)

5. Group Analysis & What Really Happened (15:00 – 16:39)

• Phil jokes about simultaneous success and failure: he managed to separate the women from the group each time but never scored a number.
• The group critiques his execution:
  • Melissa: “No, no, no, no. I’m not really hearing the part where it worked.” (15:12)
  • Producer Tracy: Points out that trying to separate a woman from a group is inherently intimidating and rare for most guys.
  • Melissa suggests the only real conclusion: “Girls need to go out in smaller numbers if they want to hook up.” (16:30)

Notable Quotes & Memorable Moments

• On failed pick-up attempts:
  • “I was doing great until she actually had to have a conversation with me.” – Phil (10:09)
• On following bad magazine advice:
  • “You never even had a chance.” – Group critique on Phil’s “rule-following” (15:39)
• On confidence:
  • “It’s all about confidence.” – Phil (16:04)

Timestamps for Key Segments

• Phil’s Mexico Vacation & Cultural Mix-ups: 01:00 – 04:54
• Introduction to the Men’s Magazine Pick-Up Test: 04:54 – 06:30
• Discussion of the ‘Rules’: 06:30 – 08:26
• Phil Tries the Pick-Up Routine: 08:56 – 15:00
  • Attempt 1 (Drink & Lesbian Excuse): 10:45 – 12:37
  • Attempt 2 (Recently Single): 13:23 – 13:57
  • Attempt 3 (Caveman): 14:17 – 15:00
• Debrief and Final Thoughts: 15:00 – 16:39

Conclusion

This episode is a classic Bert Show mix of comedy, real talk, and awkward social experiments. Phil proves men’s magazine advice is far from foolproof, highlighting the challenges (and humor) in actually “picking up” women at bars, especially when groups and social dynamics are in play. The hosts’ playful banter, relatable storytelling, and highlight on confidence keep the tone light—even as Phil racks up three memorable rejections.

Bottom Line: For the vast majority of men, separating a woman from her flock in a nightclub setting is far tougher than men’s magazines suggest—and sometimes, it’s more about the group dynamic than the pick-up line.