Vault: Phil Tries Men's Magazine Test To Pick Up Women

Summary

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.

Transcript

[Ryan Seacrest]

Hey, it's Ryan Seacrest for Albertsons N Safeway. Flu season is here and our pharmacies have you covered with a free flu shot with most insurance plans. Plus it's cough and cold season. And now through December 2nd. Stock up on all the season's essentials and get ready for relief with discounts on items like Mucinex, cold and flu, Kickstart, Mucinex, Fast Max products, Vicks, Dayquil and nyquil Combo pack. Alka select, also Airborne and afrin. Offers end December 2nd. Restrictions apply and offers may vary by location. Visit Albertsons or Safeway.com for more details.

[Capital One Bank Guy]

Banking with Capital One helps you keep more money in your wallet with no fees or minimums on checking accounts and no overdraft fees. Just ask the Capital One bank guy. It's pretty much all he talks about in a good way. He'd also tell you that this podcast is his favorite podcast too. Ah, really? Thanks, Capital One Bank Guy. What's in your wallet? Terms apply. See capitalone.com bank capital1na member FDIC.

[Phil Serena]

Hey, the bird show. Phil Serena is back from vacation.

Hola, mi amigos.

Como estas?

No es no bien. No bien, no bueno.

We're cover a lot of ground with Phil today on his vacation in Mexico.

Oh, it's excellent. I hate America right now. This is the last place I want to be.

Where in Mexico did you go?

Place called Barcelo Maya Beach. It was about an hour south of Cancun, about 20 minutes south of a little town called Playa de Carmen. And we did the whole resort package, the whole all inclusive. And if you ever go down to Mexico or you know, go to the Caribbean, that's the way to go. Just pay one price right there. We got our money's worth. We got our money back in airfare and hotel alone. And then and you know, an all inclusive, you get food and drinks involved as well. So I mean, I think I drank my weight and, and, and pina coladas and rum all weekend.

They were like, we got to get this gringo out of here. We are so going to be out of business next week.

What does gringo mean?

I kind of like white dude.

Oh, is that it? Yeah. Okay, good, good. Cause a couple people called me gringos and I was like, hey, thank you. No, I don't know to hit you or to shake your hand.

[Melissa]

Started chest butting him like, what are you talking about, huh? You want some of this American stuff, huh?

[Phil Serena]

What's up? Bring it. Do you want to. Can I tell you a quick Story now. Sure. Okay. You'll like this. So I don't know if y' all have noticed, I'm a big Georgia Bulldogs fan. And I even describe. Describe exactly what that looks like on my shoulder.

[Producer Tracy]

It's the Georgia G, right?

[Phil Serena]

And describe there's. It's the black circle G. And then all Georgia fan knows. And then there's a red circle that goes around it. A little bitty red circle that goes around it. So we get down to Mexico, and it's our first day out in the water or just out in the pool, out playing around, and I'm wearing it. No, I didn't go shirtless. And you're still not going shirtless. I couldn't do it, really, because you know what? I stopped because after I took the pictures, I kind of started drinking again. I haven't been training as hard as I wanted to, and I'm still just not as comfortable as I want to be with my body. But, I mean, I was comfortable enough with myself anyway. I wasn't shirtless, but I had, like. It wasn't like a redneck, you know, tank top on with pit stains or anything, but it did have. I did have, like, a muscle tee on the whole weekend. And I wasn't your k. Fed wife beater. No, that one. I left it here.

[Melissa]

Too many cigarette holes.

[Phil Serena]

Yeah. And so we get down there, and I had a sleeveless shirt on, and I'm walking around, and I'm noticing the first thing that happens as we're at the pool. You know, a lot of the. The workers. You know, any of these resorts have thousands of employees, and they're all walking up, you know, do you need anything? Do you need a drink? And can I get you anything? Do you need directions around? Welcome. Everyone's being real friendly. However, I also noticed that the only people being overly friendly are the guys. So I'm like, no, I'm fine. There's a group of us. There's like 10 of us there. So we're walking around, and people are asking me, asking me, what can I get you? What can I get you? Hola, amigo. Como tiames. And I'm like, marcos, what the hell's going on? So finally, I asked the girl up at the front desk, and she sees my circle. I had the shirt on. I have a circle G on my shoulder. And then she goes, oh. She goes to novio. And I said, no, no novio.

[Ryan Seacrest]

No.

[Phil Serena]

No novio. What's that?

[Ryan Seacrest]

Boyfriend?

[Phil Serena]

That's boyfriend. And so I said, no. Why? Kay. Kay, why? Apparently in the Latin and Hispanic culture, homosexuality is not taken very well. So when a lot of the Latin and Spanish men, they used to go out, and when they would go out into public to pronounce their homosexuality to other men, they would paint on other a G on their shoulder. No way.

[Melissa]

That is funny.

[Phil Serena]

So come to find out, a lot of the men down there thought I was gay because I had a G painted on my shoulder.

[Melissa]

So then you put a T shirt on instead of that muscle shirt.

[Phil Serena]

But come to find. And the truth is, the only reason it's not is because I have it circled in because there's a red circle going around it. So I had to explain to his neck, no, football. Football, College football.

[Melissa]

Oh, and you go down to Mexico to football and soccer.

[American Giant Representative]

Yeah.

[Phil Serena]

Ye.

[Melissa]

You're screwed all over the place.

[Phil Serena]

I'm a gay soccer player now.

It's good to see that you can't hook up with women in our country or south of the border. Also, some things translate to every country. Well, before Phil left for vacation, we sent him out on his latest homework assignment from these men's magazines. Because I read these things and sometimes I'm flipping through the advice, you know, like they give to other guys, and I'm like, this makes no sense to me. And it would just make more sense if women gave guys advice in these magazines and guys giving advice. Right. And as a guy, like your biggest fear and biggest challenge when you're out at a bar. Because we have been told for the longest time that if there is a bunch of women around and they're out on a girls night out or whatever, that is like, off limits. I mean, you don't have numbers on your side. It is very, very intimidating to try to approach a group of women when you see one of them that you're very attracted to. Well, askmen.com gave a whole bunch of different instructions on how you could do just that. If you're a single guy at a bar and you see four or five different women and there's one in the pack that you were just digging on, they gave like four or five different instructions on exactly what to do in order to separate her from the pack and do it successfully. So I. I mean, I have had roommates that were really, really, really good looking. And it is very, very, very rare that any guy can actually get this done. But when you read askmen.com they make it sound so easy. You just follow these rules, no worries. So we sent Phil out with those rules in hand to see if it would actually Work on a group of women. And it was so long ago that we did this. I don't even remember what the rules were.

Well, the rules were simply you would see the group of women, you know, for lack of a better term, the herd of women together. The group of women together. And you would not heard.

Definitely not heard, Definitely not heard.

[Melissa]

The herd.

[American Giant Representative]

The flock.

[Phil Serena]

Flock of women. You'd see the group of women together, and you would focus in.

Is it Andy Walker at all? This guy is getting sex in Georgia.

Baby, I like your udders.

[Melissa]

Or in Latin America, either, so.

[Phil Serena]

Thank you. So you'd see the group of women together, and you would focus in on one of them. And per the rules from AskMen.com, you would either a buy want to drink. If, like, you know, let's say I focus in on you, Melissa, and I notice you're drinking, you know, a Bud Light, I would buy you a bud Light, and either I'd send it to you, or I'd take it over to you myself. And with that charm, the other group of women as well, you know, hey, how you doing, everybody? Having a good time tonight? What's the occasion? Girls night out. All great. And then you would just simply, per askmen.com, ask Melissa. Hey, can I talk to you for a couple seconds? Hey, can I pull you to the side? I just love to talk to you for two seconds. And that's basically. That's all the rules. And per the conversation, you. You just feel it out from there. And your ultimate goal is to get the phone number from the girl.

It's starting to come back to me now. Wasn't the first rule, like, buy her a drink, let her know that you're the one that bought the drink, but don't approach her immediately. Just let her and her friends kind of like, debate over who you are, what you look like, and then almost like, forget that you're the one that bought her the drink. And then later in the night, you make the approach. I think these are the rules, right? And you're supposed to win over the rest of the women in the group, especially the one woman that's always hardcore about, hey, it's a girl's night out.

Mother hen.

The mother hen.

[Melissa]

You're supposed to make friends with her.

[Phil Serena]

That's right. You definitely got to win her over. And then once everybody in the group accepts you, then you kind of break off into, like, a sub conversation with the girl that you were initially attracted to. Before you know it, you have her away from the rest of the pack.

And this. And I'll tell you this once again, because we've tested these theories before. About the first time we did it was how to pull a woman away from her guy as they're on a date. And it worked. And once again, the one key factor that you have to have in doing any of these stupid men's rules from these men's magazines and websites. Confidence. Confidence. Confidence. That is all it takes. So again, I had the assignment to go out, pull a girl away from her flock, and then get her number, her herd.

[Melissa]

Her herd, her gaggle girls, and then.

[Phil Serena]

Get her number by the end of our conversation. And I'll tell you this, I succeeded and I failed miserably at the same time. Okay, here's what happened. So the place I did, I did this combination of a couple of different clubs and bars. I went to the places I did it. This is. I think these are the top three. They didn't have, like, waitress service. So most of the time, I think on these three as well, I had to take the drink over there after making initial eye contact with the girl and with the flock gaggle of women, and take the drink over there and then talk to the girls from there and pull the girl away.

See, now, if you failed, I would say you couldn't follow the askmen.com rules right off the bat. So that's maybe why it didn't work out.

Well, the only reason that it didn't work out, and you'll hear this, is because with each attempt, while I. I was able to get the girl away from her flock and was able to initiate conversation. Couldn't get one phone number out of it.

[Melissa]

Oh, no.

[Phil Serena]

So I was able to get the girl away.

You were halfway home.

Exactly. So I failed.

[Melissa]

But it was when you were one on one with her.

[Phil Serena]

One on one. One on one with her.

That's an entirely different topic.

[Producer Tracy]

For another topic, that's another askmen.com set of instructions.

[Phil Serena]

I was doing great until she actually had to have a conversation with me.

So what you're going to hear is this first. This first group of. This first piece of audio is I saw the group of girls. I noticed she was drinking a drink, and I had a drink in her hand. I actually had to physically buy the drink, Took it over to the girl and. And unfortunately, the audio of me charming the women was very simple. It was very loud at this club. But it's just me saying, hey, how y' all doing? You having a good time? Great. I got you a drink. And this Is me taking a step over with the first girl that I met at the club. After I handed her, put a drink in her hand.

[Club Woman]

I've kind of been watching you from across the club, you know, Hope you're enjoying your drink, hope you're having a good time. You know, I just want to pull you away and I like, just curious if I can get your phone number. I'd love take you out sometime. What are the chances that leave tonight with your phone number?

I'm very flattered, but my girlfriend over there is going to take me home tonight. Would be very happy if I gave you my phone number.

What if I talked to her? What if I talked to her and I said, look, I promise, you know.

[Phil Serena]

You don't have to come home with me.

[Club Woman]

I'm just looking for like a phone.

[Phil Serena]

Number, you know, I couldn't quite make out what she said. She said, my friend over there is.

My girlfriend over there would not like it if I left with or if I. My girlfriend would not like it if I left her tonight.

What does that have to do with giving you the phone number?

Keep listening.

[Club Woman]

I don't want to take you out tonight. Maybe in the future, since she's my.

Girlfriend and she's the one taking care of me tonight, she probably won't like that.

So it probably is not going to happen. Oh, so when you say girlfriend, you mean girlfriend, Right? So I'm probably. Probably shooting in the wrong direction here.

[Producer Tracy]

Right.

[Club Woman]

So it's not going to happen.

[Phil Serena]

So she's claiming that she digs chick.

She's claiming she was a lesbian.

Okay, never had a shot at that. But you also violated the last time we did this, the rule of obtaining a phone number. You didn't. You didn't keep. The education that you got the last time is you don't. You don't give them the opportunity.

You tell them, you tell them.

You say, give me your phone number so I can put it in my phone. You don't make it an option, like.

[Melissa]

And you know she was lying, right?

[Phil Serena]

Yeah.

[Melissa]

Okay, thanks.

[Phil Serena]

Cause you know that voice. No, no, no, no.

[Producer Tracy]

I'm just.

[Melissa]

The way she was doing it.

[Club Woman]

She's not in my community.

[Melissa]

She was just trying to. She was hesitating, hesitant.

[Phil Serena]

What do I say?

[Melissa]

What do I say? That girl over there, she's gonna take care of me tonight.

[Phil Serena]

Yeah, not happening.

So test number one failed miserably. So in my mind, I'm like, okay, she's lesbian. Fine, no big deal. No, no, no. My pride, my. She must be a lesbian. She don't want none of me.

She would have seen that G Death tattoo indicating that you were gay. Maybe that. Then she would have dug.

[Melissa]

Yeah.

[Phil Serena]

All right. So once again, I try again. Same situation I managed to get. Now I was just hurting another girl in this one, so managed to. Another drink in my hand. Can I expense all these drinks I bought for these women because I spent.

Sure, you try that kind of thing.

I like that. So once again, I managed to get her away from the. From her. It was just her other girlfriend. She never took the drink, which was my first indication this probably wasn't going to work at all. So here's number two.

[Club Woman]

I was watching you from across the bar. I hope you're enjoying your drink. I hope you're having a great time tonight, but a little nervous. My question is, I'd love to be able to get you a pumpkin. I'm just. I'm really trying to. I'd love to be able to take you out sometime. Maybe dinner or something. What are the chances I can get your number?

I'm sorry, you can't get my number right now. I'm just getting out of relationship, and I'm out with my friends trying to have fun. I'm not really out for that right now.

Well, I mean, if you're looking maybe to, you know, step back into the game or maybe, you know, just. If you want to vent to me, you're more than welcome to.

No, that's okay.

[Phil Serena]

Thank you.

Anyway.

So she's just getting out of relationship.

I'm sure she is. She's probably getting out of relationship with another girl the way my Lucky Strike 2 fail miserably. All right, so now my confidence is starting to lack just a little bit. Final time. This girl wasn't even drinking. I just walked up and pulled her away from her group of friends.

So you threw all the rules out the window.

Now this. I'm on my own personal conquest just to get a damn number.

So this is just caveman stuff now.

This is. Yeah, this is pretty knuckle on the ground.

[Club Woman]

I think you're really attracted. I do. I've been watching you. You know, I'm pulling you away from your girls just because I want to talk to you for two seconds. What are the chances of tonight? I could get your phone number.

Less than that.

I have a boyfriend, but he's not.

[Phil Serena]

Here tonight, is he?

[Ryan Seacrest]

No.

[Club Woman]

So what are the chances, you know?

[Phil Serena]

Are y' all serious?

[Club Woman]

But his brother's here.

[Phil Serena]

Okay, that's cool.

[Club Woman]

But, like, you know.

Yeah, I'm Getting in trouble just talking to you right now.

So there's nothing.

[Phil Serena]

Ouch. Dude, you make me so uncomfortable.

Don't worry. I make myself so uncomfortable. So it worked, and I failed at the same time. So it's a confidence. If you can get over there. And again.

No, no, no, no. I'm not really hearing the part where it worked.

I got the girl away from her flock. Well, yeah. You physically pulled her away the third time. I had to. It's the only way I was gonna get her to talk to me.

I think the initial mistake you made was you didn't follow where you needed to be at a place where you sent the drink over, and then her and her friends got to debate you from afar. So you never even had a chance.

Thanks, buddy.

You never even had a chance.

[Producer Tracy]

But I know that has worked for.

[Phil Serena]

You in the past, though.

[Producer Tracy]

I remember when you were out with producer Tracy at the place in Atlantic Station.

[Melissa]

I'm drawing a blank right now.

[Phil Serena]

Beach party.

[Melissa]

Strip.

[Phil Serena]

Strip.

Strip.

[Producer Tracy]

Didn't you do the send the drink thing at Strip?

[Phil Serena]

No, at Strip, I had a girl send a drink to me. Oh, that's what it was.

[Melissa]

Yeah.

[Phil Serena]

And she conquered. She was awesome. She won. She did a better job than I did.

Because she followed the rules.

She followed the rules exactly. It's all about confidence.

6:36. Now it's all the hits. Q100 in the version. I'm not really sure what conclusion to draw from that because I don't feel like it was done 100%. So that is the most intimidating task, to see the group of people and try to approach them. It's still not even 99% of guys could not pull that off. So actually.

[Producer Tracy]

Actually, the conclusion is that girls need.

[Melissa]

To go out in smaller numbers if they want to hook up.

[Phil Serena]

Far less intimidating. Far less intimidating. Hey, the Birch Show.

[Capital One Bank Guy]

Banking with Capital One helps you keep more money in your wallet with no fees or minimums on checking accounts and no overdraft fees. Just ask the Capital One bank guy. It's pretty much all he talks about in a good way. He'd also tell you that this podcast is his favorite podcast too. Ah, really? Thanks. Capital One Bank Guy. What's in your wallet? Term supply. See capitalone.com bank Capital One NA Member.

[Producer Tracy]

FDIC at Capella University, we believe accessible education can make a difference in people's lives. That's why we offer scholarship opportunities to all eligible students. Whether you're considering a bachelor's, master's or doctoral degree, our teams will walk you through the process. And help you get the savings you are eligible for. Furthering your education is an investment in yourself and tons Es que estas un futuro diferente esta macerca de loca cres con Capella University. Learn more at capella.edu with the state.

[American Giant Representative]

Of today's economy, it's more important than ever to invest in products that last for years to come. As the seasons shift and get cooler, make sure your closet is stocked with durable layers that stand the test of time From American Giant American Giant's clothes work harder and are wearable season after season. Their greatest hoodie ever made is made from the highest quality materials that are cut and sewn right here in the United States, so you're investing right back in your local community. Choosing American Giant means taking a stand for American manufacturing and hard working Americans. Something other mega corporations don't care about. From fleece to knit, all in a range of colors for versatile daily wear, American Giant delivers everyday pieces designed for everyday life. Feel the difference of quality made to last clothes from American Giant Get 20% off your first order with code [e-mail] that's 20% off your first [e-mail] with code STAPLE20.