Vault: She wants to date like a man

Summary

The Bert Show – “Vault: She Wants to Date Like a Man”

Date: June 3, 2026
Hosts: Bert (Birch), Jen Hobby, Melissa, Marcus
Theme: Exploring modern dating, authenticity, and the challenge of letting go of old relationship patterns.

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Episode Overview

This episode dives into the ever-relevant question of whether women can–and should–“date like men.” The core conversation revolves around co-host Jen Hobby’s attempt to break out of her serial monogamist tendencies by dating multiple people at once, a process she finds both empowering and uncomfortable. The Bert Show cast and listeners weigh in on the double standards, emotional pitfalls, and personal growth that come with navigating non-exclusive relationships.

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Key Discussion Points & Insights

1. Personal Struggles With Identity in Dating (00:29)

• Bert opens with reflections on how everyone struggles to reconcile who they are with who they want to be in different areas of life.

• Jen Hobby admits to striving for a dating style she’s not sure fits her true self.

  “It’s who I want to be, but it’s who I’ve said that I want to be. Does that make sense?”
  — Jen Hobby (01:15)

2. Jen’s Relationship History & Motivation (01:45 – 02:39)

• Jen has spent most of her adult life in just two serious relationships, starting in her teens.

• Coming out of her last monogamous relationship, she publicly resolved to “date like a man,” embracing a wider net and casual dating.

  “The idea was, she came on and she’s like, ‘I am going to date like a man.’”
  — Bert (02:32)

3. The Struggle of Serial Monogamy vs. Casual Dating (03:16 – 06:05)

• Jen confesses that despite her efforts to date multiple people, she naturally gravitates toward exclusivity with someone she feels a strong connection to.

• Melissa challenges Jen to admit her true preference, calling her out for creating expectations – both for herself and for her friends or dates – that she doesn’t genuinely embody.

  “You are a serial monogamist. You try dating but you don’t like dating. You like being in a relationship better.”
  — Melissa (03:43)

• The group also discusses the tension between enjoying independence and the guilt around seeing multiple people once an emotional connection forms.

  “As things progress and become more intimate… it feels like you’re being unfaithful or something. But at the same time, there’s been no discussion of being exclusive.”
  — Jen Hobby (04:01)

4. Double Standards & Gender Dynamics in Dating (04:48 – 07:43)

• The cast discusses how dating multiple people is often more accepted for men (“dating like a dude”), while women–including Jen–tend to get emotionally invested sooner.

• Bert argues that playing the field can make someone more attractive, pushing for confidence and scarcity as an asset:

  “If it comes up, you’re allowed to say, ‘Yeah, I’ve got plans on Friday night.’ And it will only drive him crazier for you.”
  — Bert (06:54)

• Jen and other women on the show push back, noting that women fear being dropped if a man finds out they’re dating others.

  “From a girl’s perspective, you feel like they are gonna go somewhere [if you see someone else].”
  — Caller (07:26)

5. Listener Calls: Real-Life Experiences (09:48 – 11:28)

• Aaron, a female caller, shares her experience: She was dating several men and, upon her favorite finding out, he asked to become exclusive.

  “When the guy that I was really interested in found out… about two weeks afterwards, he actually came to me and asked me to be exclusive with just him.”
  — Aaron (09:57, 10:19)

• Marcus, a male caller, offers a contrasting viewpoint, saying not all men become more interested if they know a woman is seeing others. For some, it’s a turn-off.

  “I’m a guy that likes to be in the serious relationship… and if I’m dating somebody and they’re talking about, ‘Hey, I got other guys,’…it kind of turns me off.”
  — Marcus (11:02)

6. Jen’s Honest Confession and Self-Reflection (11:45 – 12:55)

• Jen admits she struggles to take real breaks between relationships, reinforcing Melissa’s point that she’s a “relationship girl” at heart.

• The group gently teases Jen for, at most, taking four months between long-term relationships.

  “What’s the longest time you’ve taken in between your monogamous relationships?... Four months.” — Jen Hobby (12:32, 12:40)

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Notable Quotes & Memorable Moments

• Jen Hobby’s struggle:
  “I’m trying so hard to be something you’re not.” — Melissa (06:01)
• The group’s chemistry:
  [Laughter and light teasing as Jen reveals she’s dating four men at once] (09:28)
• Melissa’s point on authenticity:
  “There’s nothing wrong with anybody doing anything. It’s just admitting it.” — Melissa (12:08)

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Important Timestamps

• Bert frames the episode, personal struggles: 00:29 – 01:15
• Jen’s relationship history and dating philosophy: 01:45 – 02:39
• Melissa calls out Jen's serial monogamy: 03:43 – 04:01
• Internal guilt about multiple dating: 04:01 – 04:48
• Authentic vs. aspirational dating identities: 06:01 – 07:09
• Listener call—Aaron’s story: 09:48 – 10:55
• Listener call—Marcus’s male perspective: 11:02 – 11:28
• Jen’s honest self-reflection: 12:15 – 12:40

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Episode Takeaways

• The desire to “date like a man” often clashes with one’s true nature—especially for those inclined toward serial monogamy.
• Emotional honesty and self-awareness are key to navigating dating without regret or internal conflict.
• There’s no right or wrong way to date—what matters most is owning your preferences and actions.
• Real listener stories reveal that gender expectations and personal preferences in dating are diverse and complicated.
• Being upfront about dating others can provoke interest—or drive it away; outcomes depend on individual personalities and values.

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In the irresistible, easygoing tone of The Bert Show, this episode explores dating, self-knowledge, and the quest for authenticity, all wrapped in candid laughs and real talk.

Transcript

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[Birch]

This is the Bird show. We all struggle. Everybody, everybody has a struggle of who they are and who they want to be in certain different areas. I want to be a guy that can go out and casually drink and not have to get my buzz on and just go home and sleep. I want to be that guy. I really want to be him. I'm not. I go out, I start drinking and I can't turn it down. I want to be a guy that doesn't have any time for the Jersey Shore or any of the MTV shows. I'm not that guy.

[Jen Hobby]

You get addicted to those.

[Birch]

Addicted. And it's a total and complete waste of my time. Jen Hobby is struggling big time right now with who she is and who she wants to be. Really?

[Melissa]

I don't know.

[Jen Hobby]

It's who I want to be, but it's who I've said that I want to be. Does that make sense?

[Birch]

Yes.

[Jen Hobby]

Anyway, it's a dating struggle, right? Because I've been single for several, several months now and dating and enjoying it and really enjoying spending time with different people and that kind of stuff. And I'm continuing to do it. But there's one person that I'm dating that I'm really, really interested in. So, you know, if we're, you know, in the sprint, there's somebody in the lead. And so what?

[Birch]

I'm just gonna add a little history.

[Jen Hobby]

Okay.

[Melissa]

Okay.

[Birch]

Jen's history is this, is that she's been married and the guy that she got married to, she started dating when she was 19 years old.

[Melissa]

Yes.

[Birch]

And that relationship lasted until she was 31. 31. Only dude she ever been with pretty

[Jen Hobby]

much from 19 to 31.

[Birch]

19 to 31. So a lot of formidable years there. They divorce and she gets back into a relationship with another guy. How many months after the divorce?

[Jen Hobby]

I'm trying to think, like, well, there was a time where I was dated. I dated one of your friends and had that dating time. And then that one was last year, like around, like December.

[Birch]

Okay. And then there was sort of like this very.

[Jen Hobby]

And then it was like eight or nine months.

[Birch]

And it was a serious relationship.

[Jen Hobby]

Fell into a serious Monogamous relationship.

[Birch]

Yes. All right. So she came out. She came out of that. And the idea was she came on and she's like, I am going to date like a man.

[Caller Female 1]

Dating is a verb.

[Jen Hobby]

Dating is a verb.

[Birch]

Date like a man. And I'm going to. I think we had suggestions. Look, you don't need to tell guys that you're going out with a whole bunch of them. But that's how that should be your attitude. Just go out with a whole bunch of them. And you were on board on that.

[Jen Hobby]

And I still am sort of.

[Caller Female 1]

Kind of.

[Jen Hobby]

I still am on board on that. Come on.

[Melissa]

Melissa can just check out her team.

[Birch]

Melissa, go ahead, please.

[Jen Hobby]

Because I think if I. I'm on board on that.

[Melissa]

I just love Jen. Jen is a sister to me. But, honey, come on.

[Jen Hobby]

I'm definitely still on board on that. And I have been.

[Melissa]

But look me in the eye and say that again.

[Birch]

I know.

[Melissa]

Without fidgeting.

[Jen Hobby]

Well, what I'm saying is that it's changing because you can't look at me. It's changing now because I'm really interested in one person more than the others. And that's kind of what dating is for, right? To, like, find, like, you know.

[Caller Female 1]

And you don't want to, like, screw that one thing up that's going so well and that you can see potential for.

[Birch]

But what I'm saying is, in the beginning of these relationships, while it's. It's cool to be excited, you're still allowed to date other guys and be

[Jen Hobby]

just as excited, which I am.

[Melissa]

But the whole issue is what you want to be and what you are, right? Because as long as you embrace the truth and know who you are, then it's fine. And you are a serial monogamist. You are a serial monogamous. And you. And you try dating, but you don't like dating. You like being in a relationship better.

[Jen Hobby]

Well, I like being single, too. I like my independence, and I like that kind of thing. But I think once you're. I don't know, I guess, like, once I'm interested in someone, I want to spend more and more time with them because I want to get to know that person better. Because there's, like, something, you know, really intriguing or there's the spark there or whatever. And then I think as things progress and become more intimate, then I think I have a harder time with continuing to date other people because it feels like you're being unfaithful or something. But at the same time, there's been no discussion of being exclusive Are you dating other people or anything? There's been. Yeah, no exclusive talk has happened, so I shouldn't feel bad about it, but I kind of feel bad about it, but I'm still doing it because I feel like I should. Does that make sense?

[Birch]

Yes and no. But if you were dating like a dude or dating, like, some of the women that we talk to that have the ability to not emotionally get invested like you do or as excited, then when you started to feel that excitement, you would sort of detach yourself and say, look, I don't want to get really serious right now. Some women will say, I just don't want to be in a relationship right now. I don't want to get serious no matter who comes my way. You're not capable of doing that.

[Jen Hobby]

I. Okay, I'm not.

[Melissa]

I am a serial monogamist. I will say that out loud. I'm a serial monogamist. I hate dating. I thought dating was boring. I thought it was shallow. I mean, I'm one of those people that. I really didn't enjoy it. Like, I mean, because I. When I met Katie, I was going out with three or four women at once, and I forced myself to make. But Katie was always, as soon as I met her, the one that I enjoyed and the most. But I forced myself to go out with these other women because I thought, you know what? This is what I need to do. Ended up with Katie.

[Jen Hobby]

Anyway, so for how long did you juggle the four?

[Melissa]

Only like a month or two. Because it's like, I.

[Birch]

This is more than most can do.

[Melissa]

And Jen's, like, saying, that's what I'm saying. But I'm admitting I'm a serial monogamist.

[Jen Hobby]

Okay, so you're just saying I need to admit it.

[Melissa]

I think that you are trying so hard to be something you're not.

[Birch]

You like being in relationships, and it's okay.

[Melissa]

We only fuss at you is because you're giving us an expectation that. That you know, like, oh, okay, you know what? I'm dating as a herb, and I'm gonna go out. I'm. And then all of a sudden, it's like. And it's like, what are you.

[Jen Hobby]

What are you doing?

[Melissa]

So it's just creating that expectation in

[Birch]

this new stage with a guy. I know that you guys are trying to hide the other dudes, and you feel somehow that it's not loyal or whatever.

[Jen Hobby]

Right.

[Birch]

It doesn't change the attitude of the guy that you're interested in to know that you're still dabbling with other Guys, it doesn't change. It makes you a hotter commodity.

[Jen Hobby]

Are you sure? That seems rude.

[Melissa]

It does seem rude, because you've given them this idea that you're into them, and then you start dating somebody else. And it feels like, from our perspective, it looks like mixed messages.

[Birch]

Yeah. And you don't have to, like, put it in his face, but if it comes up, you're allowed to say, yeah, I've got plans on Friday night. And it will only drive him crazier for you.

[Jen Hobby]

Really? Make him offended.

[Birch]

No, it will force the conversation, probably if he's at the same place that you really are or you're hoping to get to. It may force the conversation with like, hey, Jen, so where are we in this whole thing? If you got plans Friday night with another guy. Is that what we're gonna do? And then you take it from there. But he's not going anywhere.

[Jen Hobby]

Okay.

[Birch]

See, but I know you don't believe it.

[Jen Hobby]

I don't believe it. It's hard because from a girl's perspective,

[Caller Female 1]

you feel like they are gonna go somewhere.

[Jen Hobby]

Yeah.

[Caller Female 1]

Like if you go and date somebody else, you feel like that guy is just gonna drop you, like, in two seconds.

[Birch]

I mean, if we're talking. If you're into a relationship for a year. Oh, well, yeah. But you're still in this whole.

[Jen Hobby]

All of it's brand new.

[Birch]

Yeah. You're allowed to be your own woman and have dates on Friday nights and next Wednesday nights. And it makes you hotter when you're not available for him in the beginning of the relationship.

[Jen Hobby]

Hmm.

[Caller Female 1]

I couldn't do it. And I know Jen can't do it.

[Birch]

I know she. I know women can't do it.

[Jen Hobby]

I am doing it. I am doing it. I'm just not super comfortable. I'm excited about all of it because, I mean, I'm not dating anybody that I wouldn't. That I'm not interested in. If I'm not interested, I'll let you know I'm not interested or you get the brush off or whatever. So I'm not gonna spend time, you know, because I feel like everybody's got busy lives, busy schedules.

[Melissa]

I.

[Jen Hobby]

My friends are very important to me, so I always make time for my girlfriends. So if I'm going to take out the time and date somebody, it's gonna be somebody that I, A, am interested in, think is a good person, and B, am attracted to. So. So, I mean, all of those things have to be there anyway. So it's not that I don't want to spend time with Anybody that I've been seeing, but there's just one that's better than.

[Melissa]

And I don't think one is worse or better than the other because it just is who. You know. Again, the point of the conversation was admit who you are.

[Jen Hobby]

Right.

[Melissa]

So I think women who can date. That's great. I mean that. Because I do think there's so many things about dating that can be enjoyable. I just didn't enjoy them, you know?

[Jen Hobby]

See, I am enjoying it. That's the thing.

[Birch]

You're enjoying what?

[Jen Hobby]

Dating and dating different people. I have totally enjoy. It's not like a burden to me to get dressed up and go out or do dinner or, like, the new conversations or, you know, or, you know, I feel like I'm a good conversationalist. I feel like I ask a lot of questions and I'm interested in other people, so it's not a burden to me to do that at all. And like I said, people I'm spending time with, I really want to spend time with. Like, I feel like, you know, the guys that I've been dating are the cream of the crop.

[Melissa]

How many guys are you juggling right now? Honestly?

[Jen Hobby]

Four.

[Birch]

Yeah.

[Marcus]

Wow.

[Birch]

Here's a little chest bump.

[Caller Female 1]

I know.

[Melissa]

I didn't even know that. Now are you dating. Are you going out with them at the same amount? I mean, the same amount.

[Jen Hobby]

There's one person I'm seeing much more than the other.

[Birch]

He's way in the lead.

[Melissa]

I was gonna.

[Jen Hobby]

He's like, laughing the other day because

[Melissa]

with Katie and the other women, I was going out with them all at the same. The same level.

[Jen Hobby]

The same level.

[Birch]

Okay, here's Aaron. Good morning, Aaron. You're on Q100.

[Aaron]

Good morning, guys. I agree with your comment that it makes you a hotter commodity if you let the guy know.

[Jen Hobby]

Really?

[Aaron]

Well, I was dating about four guys up until about a month ago, and I was interested in just one mainly. But I still wanted to see what the other guys did. And when the guy that I was really interested in found out I was dating about two weeks afterwards, he actually came to me and asked me to be exclusive with just him.

[Jen Hobby]

And that's what you wanted at the time?

[Aaron]

Yeah, that's what I wanted at the time. Because I was in a serious relationship for two years, and I just. I was in the whole. I just don't want to just date one guy. I just want to, you know, have my freedom, do whatever, like Jen said, not answer to anybody. And me and him hit it off really well. But I still was like, Well, I don't want to get tied down with anybody, but I really do like him, and I like the time that we'd spent together and told him that, you know, I have plans these nights. I'm going out with a couple other guys and whatnot. And then about two weeks later, he finally came to me and was like, look, I don't want to basically have to share you if I don't have to.

[Jen Hobby]

Okay, that's good advice.

[Birch]

But for every call we're getting there, we're getting a guy calling up saying that my advice is bad. Hey, Marcus. Good Morning. You're on Q100.

[Marcus]

Hey, what's up, man? I just want to say that not all guys think that way. Like, some guys, you know, when they're in that really were like, they're trying to get with that girl and they really like her, she's dating other people. It. Sometimes it turns them off, you know? Like, I'm. I'm a guy that likes to be in the serious relationship, and if I'm dating somebody and they're talking about, hey, I got other guys, they. It kind of turns me off, and I find somebody that's looking for the same thing that I'm looking for, so.

[Birch]

But you're not even in that phase yet. What I'm saying is, by him knowing that you're still dating other guys and not making yourself available, that doesn't mean that you're saying I'm not open to a relationship with you. It's just you saying I'm still doing other things. You're not at the epicenter of my dating world.

[Melissa]

Have you turned him down for something and already had plans, or are the other guys there to fill in the gaps when he's not available?

[Jen Hobby]

It hasn't been that long yet to figure it out.

[Melissa]

Okay.

[Jen Hobby]

I don't think it's like, you guys

[Birch]

are still in the very beginning stages of this whole thing.

[Jen Hobby]

Yeah.

[Aaron]

Yeah.

[Birch]

I think there's nothing wrong with you juggling four dudes the same way. There's nothing wrong with a dude.

[Melissa]

There's nothing wrong with anybody doing anything. It's just admitting it. Admitting it. I can't admit it, Melissa.

[Jen Hobby]

Well, I think what it is, is I can admit it. I know that. I know that I am a relationship girl. I know that I am. And so I've been trying to sort of, like, break that pattern, you know? Cause you don't want to be somebody that goes from one to the next to the next to the next to the next. You know what I'M saying you want to, like, take that time in between and all that kind of stuff, but I'm not very good at it.

[Melissa]

What's the longest time you've taken in between your monogamous relationships? And I'm not judging because I'm that girl.

[Birch]

No, I know. It's been, like, a good. It's been a solid 72 hours.

[Jen Hobby]

Well, it's only happened twice in my life, so. Since your divorce, like four months, probably. Four months.

[Birch]

Okay, four months. And what does that say? The four months part.

[Melissa]

She's a serial monogamist.

[Birch]

This is the Birch Show.