"Is Flirting a Power Move in Business… or a Disaster Waiting to Happen? Help!"

Summary

Podcast Summary: "Is Flirting a Power Move in Business… or a Disaster Waiting to Happen? Help!"

Podcast Information:

• Title: Help Wanted
• Host/Author: Money News Network
• Description: Do you have a work problem? We have solutions. On Help Wanted, Entrepreneur editor-in-chief Jason Pfeiffer and money expert Nicole Lapin help you stay ahead of the curve and make money doing what you love — no matter if you’re trying to impress your boss, or if you ARE the boss.
• Episode: "Is Flirting a Power Move in Business… or a Disaster Waiting to Happen? Help!"
• Release Date: August 12, 2025

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Introduction to the Topic

In this episode, hosts Jason Pfeiffer and Nicole Lapin delve into the nuanced topic of flirting within professional settings. They explore whether flirting can be an effective tool for career advancement or if it poses significant risks that could jeopardize professional relationships and reputations.

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Personal Anecdotes and Initial Discussions

Nicole Lapin begins the conversation by sharing a personal story about her experience with contractors during a home move. She recounts how her husband questioned whether her compliments to a contractor were borderline flirting, prompting her to reflect on her intentions and perceptions.

• Nicole Lapin [02:14]: “If that's flirting, then I really don't know.”

Jason Pfeiffer engages by relating it to his own experiences, highlighting the thin line between being friendly and flirting in professional interactions.

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Defining Flirting in the Workplace

The hosts grapple with defining flirting within a business context. Jason admits his confusion about what constitutes flirting, both in recognizing it when it happens and understanding its implications.

• Jason Pfeiffer [05:15]: “But the reason we're doing this as a whole episode is because you said… that you don't mind being a little flirty if that gets a better deal.”

Nicole adds that flirting often depends on context and the perceptions of those involved, making it a subjective experience.

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Flirting as a Strategic Tool

The discussion shifts to whether flirting can be used strategically to achieve better outcomes in business transactions. Jason compares this to service workers who might be more personable to earn better tips, questioning if similar tactics are appropriate in other professional interactions.

• Jason Pfeiffer [07:13]: “I think that if you are in a position to just be really nice to someone else as a means of producing a better result on anything, that is totally worth doing.”

Nicole considers the balance between being friendly and inadvertently setting flirtatious undertones, emphasizing the importance of maintaining professional boundaries.

• Nicole Lapin [10:39]: “At what point does that come across as flirty versus just really nice?”

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Perception vs. Intention

A significant portion of the episode focuses on the disparity between the intent behind friendly behavior and how it is perceived by others. Jason shares an anecdote about a former candidate for a position who was overly flirty via email, illustrating how such behavior can blur professional lines.

• Jason Pfeiffer [22:10]: “She didn't get to the final round because she didn't have the goods, you know, like it wasn't good enough. But I'd say in those early rounds she definitely got more attention from me because of how she was sending messages.”

Nicole underscores the importance of context and mutual understanding, noting that what one party considers friendly, another might interpret as flirtatious.

• Nicole Lapin [12:26]: “I think that flirting has to do with the context and also the perception that the receiver is bringing to it.”

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Navigating Professional Boundaries

The hosts explore strategies for maintaining professionalism while being personable. Jason discusses the challenges of balancing friendliness without crossing into inappropriate territory, especially in situations where clear boundaries are essential.

• Jason Pfeiffer [31:00]: “If you have to ask yourself, is this sketchy? I think you probably already answered the question.”

Nicole adds that setting and respecting boundaries is crucial, particularly in environments where power dynamics are at play.

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Impact on Relationships and Professional Reputation

Nicole brings attention to the potential long-term impacts flirting can have on professional relationships and reputations, especially in the age of social media where interactions can be easily documented and misconstrued.

• Nicole Lapin [15:43]: “But if somebody twists it that way, still is the story. I did invite you to my hotel room. I did invite this guy upstairs to have a drink. It was a coffee drink. And so that's their interpretation of the same set of facts.”

Jason reflects on how modern professional environments necessitate greater caution to preserve both personal and professional integrity.

• Jason Pfeiffer [23:28]: “So I don't want me to. I wouldn't write something flirty back to her. That could then get screenshotted and put on LinkedIn. That would undercut me professionally and personally.”

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Takeaways and Conclusions

As the conversation wraps up, Nicole and Jason offer key takeaways for listeners navigating the fine line between being friendly and flirtatious in professional settings.

• Nicole Lapin [31:37]: “If you have to ask yourself, is this sketchy? I think you probably already answered the question.”
• Jason Pfeiffer [31:49]: “The line is if you have to ask yourself, is this sketchy? I think you probably already answered the question.”

They emphasize the importance of self-awareness, context, and mutual understanding in determining whether behavior may be perceived as flirting. Additionally, they suggest that if an interaction makes you uncomfortable or requires justification, it’s likely crossing professional boundaries.

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Final Thoughts

The episode concludes with Nicole and Jason reiterating that while being personable and friendly is beneficial in fostering positive professional relationships, it's essential to remain vigilant about how such behaviors are perceived. They advocate for clear communication and maintaining professional integrity to avoid misunderstandings that could have lasting repercussions.

Nicole Lapin [31:06]: “The line is whatever they're comfortable with is the line. If you're uncomfortable telling them, then you probably know what the answer is.”

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Conclusion

"Is Flirting a Power Move in Business… or a Disaster Waiting to Happen? Help!" provides a comprehensive exploration of the delicate balance between friendliness and flirting in professional environments. Through personal anecdotes, thoughtful discussions, and practical advice, Nicole Lapin and Jason Pfeiffer equip listeners with the insights needed to navigate interpersonal interactions without compromising their professional standing.

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Notable Quotes:

• Jason Pfeiffer [05:15]: “But the reason we're doing this as a whole episode is because you said… that you don't mind being a little flirty if that gets a better deal.”

• Nicole Lapin [10:39]: “At what point does that come across as flirty versus just really nice?”

• Nicole Lapin [31:37]: “If you have to ask yourself, is this sketchy? I think you probably already answered the question.”

Transcript

[Nicole Lapin]

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[Jason Pfeiffer]

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[Nicole Lapin]

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[Unknown]

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[Jason Pfeiffer]

This is Help Wanted, the show that makes your work work for you. I'm Jason Pfeiffer, editor in chief of.

[Nicole Lapin]

Entrepreneur magazine, and I'm money expert Nicole Lapin.

[Jason Pfeiffer]

On Tuesdays, Jason and I answer the.

[Nicole Lapin]

Helpline and solve their work problems.

[Jason Pfeiffer]

And on Thursdays, I give you one way to improve your work and build a career or company you love.

[Nicole Lapin]

And it starts now.

[Jason Pfeiffer]

Nicole, I do not know what flirting is for context. Why are we talking about this? We're talking about this because you were telling me a story, which you are about to tell me now, recording this podcast.

[Nicole Lapin]

How about I'll start with the story?

[Jason Pfeiffer]

Start with the story.

[Nicole Lapin]

Okay, so I'm moving. Yay. Finally found a place.

[Jason Pfeiffer]

Good.

[Nicole Lapin]

Have a bunch of contractors in the house. And the other day my husband was like, are you borderline flirting with this guy? It was very nice with them. And what were you doing? Asking them to hang a painting or something? I don't know.

[Jason Pfeiffer]

If that's flirting, then I really don't know.

[Nicole Lapin]

Flirting, I think I said.

[Jason Pfeiffer]

Did you say, hey, sexy, can you hang that painting?

[Nicole Lapin]

No, it was something like they needed to pick up something really heavy. And I said something like, wow, you're so strong.

[Jason Pfeiffer]

Positive reinforcement.

[Nicole Lapin]

Yeah, something like that. Not, oh, baby, you're so strong. Yeah, no, it wasn't in that sense, but it was like a compliment. And I think that, you know, I said to my husband, no, I'm certainly not flirting with this man. No intention of flirting. I stopped, and I wondered where that came from.

[Jason Pfeiffer]

Where the potential that you were flirting came from.

[Nicole Lapin]

Yeah.

[Jason Pfeiffer]

Or, like, why did you compliment the guy in the first place?

[Nicole Lapin]

Sure.

[Jason Pfeiffer]

Okay.

[Nicole Lapin]

And so I remember being single for the majority of my adult life and having contractors over and being a single woman and needing to sort of protect myself and be overly nice so that they wouldn't take that large object that they picked up and throw it at me or hurt me or, you know.

[Jason Pfeiffer]

If there was any insinuation that I.

[Nicole Lapin]

Was being rude or something, that I was a small, single lady and couldn't really defend myself. So I think overcompensated.

[Jason Pfeiffer]

It was like a safety thing, almost. Well, it was. It was. It was being nice, but being, like, overly, very intentionally nice to just make sure that the situation remained co. Set up. Yeah, yeah. And that now you've got this muscle.

[Nicole Lapin]

Memory, potentially, and husband, muscle man. And so maybe I'm just an asshole.

[Jason Pfeiffer]

Was Jared amused when he said, were you just borderline flirting, or was he annoyed that you were borderline flirting?

[Nicole Lapin]

I don't think he thinks, like, the contractor was a threat, although we've heard these types of stories before, so. No, I think he just said it. And it made me reflect on, like, I sometimes have been told that, like, I come across as flirty when I'm overly friendly and bubbly, and I'm not. You know, when I worked at CNN in Atlanta, everybody says, like, honey and sweetie as sort of pet names, and. And when I was at Bloomberg, I said one of those things to some man, I think, and an executive producer said, be careful of saying that. Don't say that in the workplace. And it gave me, you know, great pause because my intention was certainly not to flirt or be flirtatious or suggestive or anything like that.

[Jason Pfeiffer]

Yeah.

[Nicole Lapin]

It just sort of was how, you know, I ended up talking naturally or being overly friendly and accommodating and things like that, but it was perceived as flirty unintentionally. And so now I've always been. I tried to be cautious because it's not my intention, but somehow it gets perceived that way.

[Jason Pfeiffer]

Right. Okay. So this was the story you told me was then the impetus for this entire podcast episode, which was I don't really know what flirting is. And this statement could also explain the long stretches of absence of love life that I had as a teenager.

[Nicole Lapin]

But the reason we're doing this as a whole episode is because you said.

[Jason Pfeiffer]

Oh, yes, right.

[Nicole Lapin]

That you don't mind being a little flirty if that gets a better deal.

[Jason Pfeiffer]

Yeah, I'd say that if I was in a position to be flirty. Again, like language that I'm not, you're going to have to describe. You need to draw a line between being nice and being flirty for me, because I'm excited to hear this.

[Unknown]

You don't have.

[Jason Pfeiffer]

Well, okay. Well, we'll talk about it. But I do think that if you are in a position to just be really nice to someone else as a means of producing a better result on anything, that is totally worth doing. I think, for example, service workers get better tips if they're really nice to people. And so they are. And so if I'm at a restaurant and the server comes by and, like, he or she, you know, is, like, very friendly and chatty, I understand that they're doing that because that's good for business. And I'm also, you know, also because it's probably coming from a place where there are people. People, and that's why they're doing this kind of work. And, you know, they're. But they're also putting it on in some way. They understand that being nice, being really nice, being like, borderline flirty, let's say, leads to a better tip. And I think that's fine. I think that's fine. And also that if you walk into a store and you're super nice and chatty with the person who you interact with, that might lead them to pay a little more attention to you or get you that thing faster. And I don't see what's wrong with that. I think that if you have the power to turn on a little bit of flirtiness and it makes the contractor do the work faster or whatever, I don't see anything wrong with that. I would be perfectly fine with my wife using that as a tool for better deals. That sounds fine to me. Does that sound crazy to you?

[Nicole Lapin]

I mean, I guess. Then to what extent? So would you be fine with Jen saying, oh, sexy. The way you lift? That is so. I mean, studly. I don't. I don't know.

[Jason Pfeiffer]

Yeah, well, she doesn't live inside of a porno like you're describing there. It's like, not the way that she talks, but sure, I wouldn't care. What does it matter? I don't know. What does it matter what somebody says to another person? Like, where this is coming from for me is simply that I think of flirty in a kind of transactional world. Like, there's a difference between being flirty at school with someone who's in your class, because that could eventually turn into, like, a relationship. But if it's like you're flirty with the waitress, you're never going to see the waitress again. This is not like a thing that's going to turn into something. It's just brightening up the interaction. Realizing also that I'm stepping into all sorts of potential gender things here. So just to be clear, what I'm really reacting to is the idea that being really nice and personable and trying to find some quick way to personally connect with people that you are otherwise having transactional relationships with can lead to better transactional relationships, and that's fine. And if some people articulate that as flirtiness and other people articulate it as just being very interested in that other person, that seems wise to me. I think that we would want to over index on defaulting to being nice to each other. And if you could turn up the brightness notch a few, I think everyone's a little happier.

[Nicole Lapin]

I don't know. There is a story. Oh, hello.

[Jason Pfeiffer]

Okay, for context, we are recording this episode in person, which we don't usually do. Usually you and I are seeing each other on Zoom, but we are in a hotel right now recording, and we just had some pancakes delivered, some room service, and the very nice guy who works at the hotel was then subjected to me grilling him about being nice and flirty and had some really good things to say.

[Unknown]

Do you think your either you or your colleagues are ever intentionally just a little overly nice with the people that you're, like, serving or interacting with? Because it will lead to a better transaction or maybe a better tip or a better anything. What do you think?

I think there is definitely always a mask that is put on. And yeah, there's like the over lining. Like, okay, maybe if I'm nicer, I will get more of a tip or whatever. But I feel like automatically you. You go into that higher pitch, like, oh, like, can I, Can I serve you?

Can I?

You know, and naturally you would do that with your family, but, like, when it's with other people, I feel like it's kind of like an automatic.

Yeah.

You know, so you don't even realize that you're doing it.

It's like an Automatic thing.

[Jason Pfeiffer]

Because it just.

[Unknown]

It almost guarantees a better outcome.

Yeah. Yeah, I'd say so. Yeah. I mean, it's way better than the opposite.

Yeah, yeah.

[Nicole Lapin]

So, like, if you're serving somebody and you're overly nice for a tip, like with the intention, like, you know, the nicer you are, the more somebody would be inclined to give a tip. At what point does that come across as flirty versus just really nice?

[Unknown]

I think that'll depend on. On the specifics of the words used in the conversation. Like, it could be a fine line. Honestly, I. I try to not really pay too much attention to it because most of the time it's at the riskier job.

Yeah.

Wanted to, you know, make anyone feel uncomfortable. Yeah.

[Nicole Lapin]

Yeah.

[Unknown]

So it's a. So flirty is in the eye of the beholder, but not necessarily in the eye of the person who's doing it.

Right. Well, thanks for sharing. D. Man, if I share some art with you guys too.

[Jason Pfeiffer]

Some art?

[Unknown]

Yeah.

Yeah.

I do make music.

Do you? Is it on Spotify? Can I find it? Yeah.

Okay. So it's called Our Love and all caps.

Okay.

And then space or rain. That's my name. O R A N E. Boom.

Hell yeah. Yeah.

I hope you guys enjoy.

[Nicole Lapin]

And right before he came in, I was gonna say that actually there's a story of the owner of the Philadelphia Eagles, Jeff Laurie, who met his now second wife, who was a waitress at his favorite Vietnamese deli and is now Mrs. Laurie. And so does happen. You know, it can go from, you know, a waitress or waiter and patron relationship too much more. Who knows? Yeah, I do think that what he said was something I wanted to double click on it being in the eye of the beholder. And so I think you and I have both been a little bit clueless about whether something is flirting or being extra nice. And sometimes it's perceived by another person as flirting because maybe they are coming to it with that perspective.

[Jason Pfeiffer]

Yeah, I mean, this is the thing that's always confused me about what is flirting, because, number one, I was definitely totally blind to when people were flirting with me. And I only knew that because somebody later would be like, she was flirting with you. And I would say, no, she wasn't. And then I would go back and have to figure out, like, what was the moment in which she was flirting with me. I was never really clear on that. But also it's the opposite where there are certainly people who perceive being flirted with when that was not what the other person was doing. And I am very sure that There is a valid counter argument to the thing that I'm saying, which is, yeah, okay, but if I'm overly friendly with someone for the purposes of getting a better tip or just getting better service or whatever, not even service industry, but also just building a better professional relationship or whatever, that can end up being perceived as leading somebody on, and then it turns into a whole other mess, and then it's, like, too personal, and I don't like that. So I want to find the line between being friendly and tipping into inappropriate, which is what our room service guy was concerned about. Like, when I asked him about what is the line between being friendly and being flirty, he had to pause and then really step back from it. And then he was like. The first things that he said was he was, like, concerned about coming off as inappropriate, which I would totally understand, because he's working here at this hotel, and if somebody calls the manager and is like, that dude who just delivered my pancakes was, like, weird and flirty with me, that is no good. That is the end of his job. So he has to find that line between being really friendly and being really flirty. But also he can't really control it because a lot of it is just how somebody else perceives it to be, for sure.

[Nicole Lapin]

And I do think it is different for. For a woman. And I've never, not once, not ever, you know, used my feminine wiles to get a job. At this point in my career, I would totally just own it. But it's not once, not ever crossed my mind. It's not been something that I've been part of. I've definitely very clearly set boundaries and rejected advances from, you know, people in the industry, but it's not like a line that I've ever crossed. However, I have had a few experiences where male friends or colleagues that I've had over the years have pointed this out to me that it could be perceived in this way. And just knowing me, you know, they know that I didn't intend it that way. Like, I used to live with my ex in New York and had a former boss come up for coffee. And I'm thinking, like, I live with somebody else. This is as, like, a convenience thing. Hey, just come up for some coffee. And he was like, you know, in this day and age, this was, like, around the me too time. And this could be perceived, like, if I told somebody else, oh, she invited me up to her place or something like that. And I was like, I never interpret it that way. Or you could say right now, oh, well, Nicole, Invited me up to her hotel room. You know, and that's certainly not my intention.

[Unknown]

Yeah.

[Nicole Lapin]

At all.

[Unknown]

Right.

[Nicole Lapin]

We're doing a podcast.

[Jason Pfeiffer]

We're doing Pancakes, Morgan.

[Nicole Lapin]

There's no funny business going on.

[Jason Pfeiffer]

Yeah.

[Nicole Lapin]

But, you know, if somebody twists it that way, still is the story. I did invite you to my hotel room. I did invite this guy upstairs to have a drink. It was a coffee drink. And so that's their interpretation of the same set of facts.

[Jason Pfeiffer]

Right. So now this gets more complicated in a way that I hadn't thought about when we were just talking about the contractor, because the contractor feels like this easy, simple thing to me, which is, well, this person is in your home, and they're in your home for a very legitimate business reason. They can't do their work without being in your home. And to be nice, I think, is to also just create a welcoming environment for everybody in this thing now.

[Nicole Lapin]

Yeah. They know your address. Like, you don't want to be.

[Jason Pfeiffer]

No. You don't want to be a jerk butthead at all. Right. So you want to be. You want to be nice.

[Nicole Lapin]

Please don't come back.

[Jason Pfeiffer]

And I've had dudes in my house pick up super heavy stuff. And I will say, wow, that was really impressive. That is way more than I could pick up. I am not flirting with.

[Nicole Lapin]

Flirting with them, Jason.

[Jason Pfeiffer]

I am genuinely complimenting them. That's a lot of stuff to pick up, and I'm impressed. But I'm also definitely doing it because there is something that I feel like needs to be addressed here, which is you are a stranger. You are in my home. I want to just create a good environment here. Also, I always carry a guilt that someone's doing something for me. Like, I'm sort of never really comfortable with that, even if I don't know how to do it myself. I can't pick that thing up. I can't fix that thing. But because I can't, you are here, and I feel a little dumb about that. And so I'm going to be really nice to you. But once we get into more complicated forms of interactions and the settings change or the settings are up for discussion, then I understand now, as we're talking about this, that you almost have to be really careful about where that perceived line is. You almost have to manage it yourself because you don't want to set the wrong expectations or perceptions. And that now starts to get exhausting. Even though I still think that. That everyone should default to being really friendly.

[Nicole Lapin]

Wasn't there a woman who was flirty with you? That you needed to draw a boundary with.

[Jason Pfeiffer]

Oh, was there. That could have happened, but I probably wouldn't have perceived it because I don't know what the hell flirting is. But do you remember the details? Like, prompt my memory?

[Nicole Lapin]

It was some woman that kept reaching back out to you.

[Jason Pfeiffer]

Stick around. Help Wanted will be right back.

So, Jason, how did that job search for the social media person go?

Ah, my inbox looks like a confetti cannon went off. Nicole, there are resumes everywhere, but I just can't tell if any of them have the right background for this role.

[Nicole Lapin]

I think you should try ZipRecruiter. ZipRecruiter finds amazing candidates for you fast.

[Jason Pfeiffer]

And right now you can try it for free with our very own [e-mail] help wanted.

And if I did give it a try, what would that look like?

Well, the moment you hit post, ZipRecruiter, super smart matching tech starts spotlighting people who actually fit the job. No more resume roulette. And when you spot someone stellar, you.

[Nicole Lapin]

Don'T have to sit around hoping they notice you.

[Jason Pfeiffer]

Zip Recruiter gives you a handy invite to apply message so you can nudge your top picks and get their applications in stat. 4 out of 5 employers who post on ZipRecruiter get a quality candidate within the first day.

Oh, that sounds perfect. What is that URL again?

Well, you can try ZipRecruiter for [e-mail] help wanted.

Got it. So that's ZipRecruiter.com help wanted.

[Nicole Lapin]

Exactly.

[Jason Pfeiffer]

ZipRecruiter, the smartest way to hire.

Welcome back to Help Wanted. Let's get to it. I mean, I don't know if this is what you were talking about. Years ago, I worked at Men's Health. I was an editor at Men's Health, and we had a column, a dating column in Men's Health called Girl Next Door. And I was the editor of the Girl Next Door column, among many other random things. And then the woman who wrote Girl Next Door, who was a staffer at Men's Health, got another job, and we had to replace her. It was my job to. To find the replacement. And there was no internal candidate that was interested, so we had to look externally. I just started putting calls out. What I ended up with was a bazillion young women, mostly fresh out of college, who all desperately wanted to write this dating column for Men's Health. There was among them, one woman whose name I cannot remember right now, who was exceptionally flirty with Me, just by email. I don't think I ever talked to her by phone, but it was undeniable that she was not just chatty, as they all kind of were, which was totally appropriate for dating comms, but offering to fly to New York whenever I wanted. And we would go out and she was. I don't know if she was planning on trying to sleep her way into this job, but I've never in my entire professional career had somebody consistently send me messages like that. And I remember being okay. And then just to set it, at the time I was 27 or 28 and I think I was dating Jen, who's become my wife. But at the time it was like a very new relationship, probably within the first couple months or year or something. And I remember being kind of fascinated by this experience and forwarding these emails to my friends, like, what is going on here? And being kind of excited to interact with her, but also being very professional because I was aware I could send something that could end up on the Internet and my job is on the line here. So I was trying to be. I felt like she was trying to be a hundred percent flirty and I was trying to be 10% receptive, you know what I mean? 90% straight man. And she ended up not getting past the rounds where we would have even done.

[Nicole Lapin]

By straight man, you mean professional man.

[Jason Pfeiffer]

Professional man. Oh, yeah, sorry, straight man in the comedic sense. I was the straightforward professional answering questions, responding to drafts. Like, you know, we would have them kind of send in sample questions and answers. But she definitely got more attention from me during that hiring process because of how she was sending messages. But she didn't get to the final round because she didn't have the goods, you know, like it wasn't good enough. But I'd say in those early rounds she definitely got more attention from me. That's me being a 20 something guy who was dating, who was having a very flirty woman come at me. And it was in the context of a dating column. So there's also that. But I haven't thought about that in a very long time. And I will admit to you that she at least got more emails back from me than other candidates did because of that.

[Nicole Lapin]

And if that happened now, oh, if.

[Jason Pfeiffer]

That happened now, I would see it as a time bomb. Like I would see it as a dangerous time bomb because it could undercut entire structures of my life, you know, And I'm also still very aware, more so now. Back then I had no public presence, but now I do.

[Nicole Lapin]

So, yeah, you're Mr. LinkedIn. Yeah, hello.

[Jason Pfeiffer]

Right, So I don't want me to. I wouldn't write something flirty back to her. That could then get screenshotted and put on LinkedIn. That would undercut me professionally and personally. I would definitely show it to my wife and be like, take a look at this. And I bet Jen would be really amused by it and she would probably prompt me to say something back that it would at least kind of get another email back. Like, it's, you know, it's kind of fascinating. Oh my God, what is this person trying to do? But no, I also felt like I was kind of still in that world of dating and now I am like a professional public dad, married guy, and so I wouldn't touch it. That would be too scary. But there's certainly plenty of people who I interact with who are just like friendly and chatty in a really fun way. And it doesn't feel flirty to me, but. But it just feels funny and smart. And those people I do actually really enjoy engaging with.

[Nicole Lapin]

So let's change the Persona of who that person is emailing you. So let's say it happened today, but the woman sending you flirty emails was a woman who was going to hire you for a million dollar speech.

[Unknown]

Oh. Oh.

[Jason Pfeiffer]

Okay. So in other words, here is a potential client of mine and there's a lot of money on the line and she is being flirty. Okay, so what does that tell me what she is saying to me?

[Nicole Lapin]

You start again. I'm not bad at the flirting.

[Unknown]

Me too.

[Nicole Lapin]

But two of us don't have any idea she's being suggestive. She is. She's this woman that emailed you back in the day, but now she's transformed into a huge speaking empire hirer person who has all the money in the world but, you know, wants to continue this conversation. But the dynamics have changed and so she is looking for some of this same type of banter, but now she has the ability to give you money because you started this by saying you would be fine with flirting for a better deal or for. To get a deal. Yeah, money.

[Jason Pfeiffer]

I think that if it's bantery, that.

[Nicole Lapin]

Sounds fine to me, but it's just really suggestive. What if it was something where it just felt like, I actually don't know if I should show Jen this.

[Jason Pfeiffer]

That would concern me because there's now travel involved and that would mean that I'm now in a different city with this person and I have accepted a offer to be there with this suggestiveness as part of the deal transaction. Because to me, that now tips into setting inappropriate expectations. Right. So I guess I really like this example because you're forcing me to find the best boundaries of this thing that I sort of said cavalierly at the beginning. Because I think a real consideration is where expectations are set. I think that if you tell the contractor they're very strong, that is not setting any dangerous expectations. But if someone is suggested, if someone is roughly speaking saying, come out, I'll give you a lot of money. Also will have wild sex in your hotel office. Hotel room. I mean, right? That's what suggestive means. Let's be straightforward about suggestion.

[Nicole Lapin]

We're not talking about prostitution here. We're talking about flirting to get a gig. So what if it's just, you know, let's. So what if it's $10 million and what if it's down the street from you in Brooklyn and you don't travel and they're going to give you $10 million? Yeah, but in order to do that, you don't need to say that she's pretty or whatever. I don't know some like innocuous word you guys are. There's not a clear or unclear agreement that there will be, you know, inappropriate activities involved. But you know, it's outside the scope of general business discussions. Like not emailing me, telling me I'm pretty. Right. She's like, I want you to do this 10 million dollar thing. Well, do you like this dress that I'm wearing and how do I look in it and whatever. And if you said, hey lady, you look so pretty, love to do this gig, it's a little bit weird, but would you do it?

[Jason Pfeiffer]

Sure. Is there anyone who would say no to that? If I took that to my wife, If Jen was here right now and it was like, jen, I can make an easy $10 million and all I have to do is tell that lady over there that she's pretty. Jen would be like, how fast can you do that? Go do that now. What else does she need to hear from you? But I mean, I also. Look, this is also different. Everybody's context is different because I am in a non jealous relationship. This is something Jen and I have talked about quite a bit. Prompted by. We have friends, friends who listen to the show. I will not name you, but hello, you know who you are. Who call each other jealous bitches. They're. They're jealous bitches with each other and we love them and they know that they're crazy and. But we've had conversations about this with them. And then on the ride home, Jen and I will have talked about jealousy because it's prompted by these conversations. And we both agree neither of us are like jealous people. I'm not concerned. If Jen wanted to be flirty with people, that just wouldn't bother me as a concept. I just don't care about that. And, you know, I have a lot of close female friends, and I'm texting.

[Nicole Lapin]

Them, and you go to their hotel.

[Jason Pfeiffer]

Room, and I go to their hotel rooms and order pancakes. I mean, in many other contexts, this sounds suspicious, but. But it's not.

[Nicole Lapin]

It wouldn't work for the jealous bitches.

[Jason Pfeiffer]

It wouldn't work for the jealous bitches, but it works just fine for us. And so if I was being, like, real chatty with someone because it's fun to be chatty with them and there's $10 million on the line, or even if there's not $10 million on the line, it doesn't really matter to me. It doesn't matter to my wife, and I know that. So the only thing that really matters to me in my particular circumstance is is there an inappropriate expectation being set with the person that I'm interacting with? And as long as I feel like the answer is clear on that, then I say chatty away because you guys.

[Nicole Lapin]

Know that it's not going to go any further.

[Jason Pfeiffer]

Yeah. Yeah.

[Nicole Lapin]

I don't know. This is a whole other episode, but I think there has to be a little bit of jealousy in a romantic relationship. Otherwise, you guys are just like brother and sister. I just feel like there has to be a little bit of fire. Like, I just. If, you know, we're hiring a nanny and one of them is really hot, and I'm just like, I'm not sure. I would rather not. And I know a lot of male CEOs who will not hire hot assistants. Now, is that discriminatory to hot women who are super talented and whatever? They just don't want to be in the position. They just don't want the temptation or the perception or the whatever.

[Jason Pfeiffer]

Right. I would be in that situation. I would be concerned not about the temptation, but about the perception.

[Nicole Lapin]

Yeah, makes sense. Totally.

[Jason Pfeiffer]

All right, so, Nicole, we've been talking about this for a while. What is the takeaway here? Aside from that neither of us know what flirting is?

[Nicole Lapin]

I think that flirting has to do with the context and also the perception that the receiver is bringing to it. And also the idea that if you can't tell your partner about it, it's probably cross the line. If you feel pause.

[Jason Pfeiffer]

Yeah.

[Nicole Lapin]

Telling your partner about it or asking for permission or something, or asking for their okay.

[Jason Pfeiffer]

Would you feel comfortable with this?

[Nicole Lapin]

If you feel like that, that you want to hide it from them or not talk about it, then it's just too far. It's gone too far.

[Jason Pfeiffer]

Right. It's like, where's the line? The line is if you have to.

[Nicole Lapin]

Ask where's the line?

[Jason Pfeiffer]

The line is like, whatever they're comfortable with is the line. Right. If you're uncomfortable telling them, then you probably know what the answer is.

[Nicole Lapin]

I think that's just a good general lesson. If you have to ask yourself, is this sketchy? I think you probably already answered the question.

[Jason Pfeiffer]

Right.

[Unknown]

Right.

[Jason Pfeiffer]

Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.

Pfeiffer and me, Nicole Lapin.

[Nicole Lapin]

Our executive producer is Morgan Lavoy. Do you want some help?

[Jason Pfeiffer]

Email our [e-mail] for the chance to have some with your questions answered on the show and follow us on Instagramoney News and TikTok MoneyNews Network for exclusive content and to see our beautiful faces.

[Nicole Lapin]

Maybe a little dance?

[Jason Pfeiffer]

Oh, I didn't sign up for that.

[Nicole Lapin]

All right, well, talk to you soon.

[Unknown]

Sa.