How to Ask Friends for Money

Summary

Podcast Summary: Help Wanted – How to Ask Friends for Money

Host: Jason Feifer (Entrepreneur magazine Editor-in-Chief)
Co-host: Nicole Lapin (Money Expert)
Guest: Jess Chermack
Date: September 9, 2025

---

Episode Overview

In this episode, Jason and Nicole wrestle with a common but awkward work-life dilemma: How do you ask a friend for money, especially in situations with social nuances—like an unexpected traffic ticket after loaning your car? With special guest Jess Chermack, they candidly unpack the financial and emotional complexities of “the ask,” offer practical scripts, and explore why even seasoned professionals get the “ick” from money talks.

---

Key Discussion Points and Insights

1. Why Asking Friends for Money Is Awkward

• Nicole admits discomfort despite her financial confidence:
  • “I have it sorted. Ish. But that doesn't make me immune from the ick of money talks. For sure. They get ick.” (03:03, Nicole)
• Two Types of Asks:
  • Asking because you need money
  • Asking for repayment for something owed
  • Both are fraught with social anxiety, even when justified.

2. Jess’s Dilemma: A Real-Life Scenario

• Jess lent her car to a friend. Later, a $75 traffic ticket for an express lane violation arrived in the mail.
• Jess faces hesitation: Should she ask her friend to pay, even though it was a friendly favor and the friend works in the not-always-lucrative theater industry?
  • “It’s $75…it’s at the end of the day, I’m never going to notice that it’s gone, but it’s taking up mental real estate, and it always will if I pay it without asking the friend…” (09:32, Jess)

3. Walking Through the Emotional Hangups

• People-pleasing and confrontation aversion:
  • “The psychology of it, I think, is just being a people pleaser and, like, trying to avoid confrontation in general. I'm a woman who was raised in America, which…I think this is like a standard narrative here.” (08:53, Jess)
• Fear of mortifying the friend:
  • “I don't want her to feel mortified.” (15:14, Jess)
• Possible friend reactions weighed:
  • “What if the friend says no?” (09:32, Jess)
  • “What if…there's just no reply or acknowledgement?” (17:18, Jess)

4. Practical Solutions: Scripting the Ask

• Keep it light, focus on the circumstance, not blame:
  • “Hey, friend, funny story. Yeah. The worst. Ate these stupid cameras…And then show her the picture.” (15:23, Nicole)
• Frame as a shared enemy (the system, not the person):
  • “Like, you're both against whoever that is. Colorado traffic enforcement people. If you're not against her, you're united in this is annoying.” (30:29, Nicole)
• Use Venmo/Zelle request functions to depersonalize:
  • “Everything is solved by the request function in Venmo.” (33:29, Jason)
• Consensus: Ask directly but gently:
  • “Cool if I send you a Venmo request?” (33:24, Nicole)

5. Addressing Anxiety: Worst Case Scenarios and Cognitive Reframes

• Stoicism and practical pessimism:
  • “What's the worst that can happen? Let's use some stoicism.” (16:06, Nicole)
• Jason’s Four Explanations Framework:
  • “There are four, count them, four possible explanations for everything at all times. And those are: a catastrophic explanation, a bad explanation, a neutral explanation, a good explanation.” (34:47, Jason)
  • This helps short-circuit the spiral of social anxiety when waiting for replies.

6. Resolution: The Ask and the Friend’s Response

• Live text drafted and sent:
  • “Hey, Colorado is apparently ridiculous and has installed random cameras on the highway...We got this ticket in the mail from when you were borrowing the car. Cool if I send you a Venmo request?” (31:10-33:43, Jess + hosts)
• Immediate positive reply:
  • “She says, ‘Fucking hysterical. Yes, please send it. I’ll pay right now.’” (36:43, Jess)
• Takeaway: The discomfort was much greater in anticipation than in outcome. Direct, non-judgmental honesty worked—the friend was gracious and unbothered.

---

Notable Quotes & Memorable Moments

• On Lending Money to Friends:
  • “If you lend a friend money, decide which you value more, the friend or the money, because it really does mess up relationships. Or I often just reframe it as a gift.” (03:40, Nicole)
• On Overthinking the Ask:
  • “This is validating the core emotional challenge of this question, which is that...everything that we come up with either feels like too weird or too pushy...when it shouldn’t.” (31:22, Jason)
• On Making it Easier:
  • “Serious. I know it exists. Yeah. I've always just texted people and been like, oh, that thing was $70. And then they Venmo me. So I've never sent the request. But now that I think about it, that would have solved the problem.” (13:08, Jason)
• On the Emotional Premium:
  • “There’s a premium to feeling like justice has been served.” (21:38, Nicole)
• Final Resolution:
  • “She says, 'Fucking hysterical. Yes, please send it. I’ll pay right now.'” (36:43, Jess)
• On Lessons Learned:
  • “May this moment right now be the reminder for most people that almost always this works out just fine. You spent a lot of time worrying about this. And actually, the whole thing could have been resolved in about 20 seconds by writing a...cheeky text and sending it off, and she would have replied 10 seconds later, and it would have all been fine.” (39:16, Jason)

---

Timestamps for Key Segments

• 03:03 - Nicole admits even money experts feel awkward.
• 04:48 - Jess introduces her car-loan dilemma and $75 ticket.
• 08:53-09:32 - Jess explores her hesitation and people-pleasing roots.
• 10:31 - Jason and Nicole agree the ticket ask is justified.
• 15:23 - Nicole’s light script & suggestion.
• 16:06 - Nicole introduces the “worst case scenario” game.
• 30:29-33:24 - Producing and revising the actual text to send the friend.
• 34:47 - Jason’s “Four Outcomes” reframing tool.
• 36:43 - Jess receives a perfectly positive response from her friend.
• 39:16 - Jason’s closing reflection on unnecessary anxiety in money asks.

---

Final Takeaways

• Most of the anxiety around asking friends for money stems from overthinking and fear of social discomfort, not the actual outcome.
• Approaching with candor, context, and a light touch—plus using features like Venmo/Zelle requests—eases the conversation.
• Treating your friend as a collaborator against an outside inconvenience (the ticket/camera, not them) preserves goodwill.
• Odds are, your friends will surprise you with understanding and quick solutions, if you just ask.

---

For listeners facing a similar pickle: Trust your friendship, be honest and straightforward, and remember: it’s almost always less awkward than you fear.

Transcript

[A]

Okay guys, I recently had my identity stolen and it was awful. It felt like a gross icky violation, like somebody got into my digital house and locked me out. Getting your identity stolen means putting a hold on your card and replacing everything. So when that happens there is no time to wait. You want to be able to get hold of your bank right away. One thing I love about Chime is that they have 24. 7 customer support available. So if you notice an unexpected charge or lose your wallet, you can connect with a real person right away to get it all sorted out. Chime also offers fee free checking accounts and ATMs. No more monthly maintenance fees. Work on your financial goals with Chime today. Open an [e-mail] helpwanted that's chime.com helpwanted Chime feels like progress. Chime is a financial technology company, not a bank. Banking services and debit card provided by the Bancorp Bank NA or Stride Bank NA Members FDIC Spot Me Eligibility requirements and overdraft limits apply. Timing depends on submission of payment file. Fees apply at out of network ATMs. Bank ranking and number of ATMs according to US News and World Report 2023 Chime checking account required When I was broke in my 20s, I was so scared to check my check because I didn't know how much money was in there, if any. And honestly, I didn't want to know. Part of my journey from money mess to money master was making sure I always knew how much money I had in each account and a plan for every dollar. One of the tools I love for this is Monarch Money. Monarch Money lets me track every dollar that I have and every dollar that I spend. But it's not just for me. It also lets me and my husband both track all of our accounts. That way we can see what's in our shared dashboard and which bills we have or haven't paid yet. It takes navigating shared finances from an annoying constant back and forth to one easy peasy peek at Monarch Money. It has saved us both so much time. While I use it to share financial information quickly and easily with my husband, it is also simple to share financial information with an advisor at no extra cost. If you've been putting off managing your money, Monarch Money is an easy way to get started. Knowing where you stand financially ultimately makes life so much less stressful and will save you so much money in the long run. Don't let financial opportunity slip through the cracks. You use code [e-mail] in your browser for Half off your first year. That's 50% off your first year. @monimalmoney.com with code help Wanted.

[B]

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

[A]

Entrepreneur magazine, and I'm money expert Nicole Lapin. On Tuesdays, Jason and I answer the helpline and help callers solve their work problems.

[B]

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

[C]

And it starts now.

[B]

Nicole, do you ever feel uncomfortable asking friends for money?

[D]

Yeah.

[C]

Who doesn't?

[B]

I don't know. I thought maybe you, because you just have this very rock solid philosophy about money, and so I just figured you would have had it sorted out in your head.

[C]

I have it sorted. Ish. But that doesn't make me immune from the ick of money talks. For sure. They get ick.

[B]

Yeah, they totally get ick. And there's this interesting nuance when I think about asking people for money, because there are two ways in which you could ask people for money. Friends, that is, which is number one, you could ask because you need money in some way. Or then number two is you could ask because they owe you money and they just haven't given you the money and it's just awkward to ask for it even though they owe it to you just because talking about money with friends is weird. And that's kind of weird.

[C]

Yeah. I mean, generally my philosophy is if you lend a friend money, decide which you value more, the friend or the money, because it really does mess up relationships. Or I often just reframe it as a gift.

[B]

Oh, yeah.

[C]

And just write it off in my brain.

[B]

Right.

[C]

And I'll give you money, but I.

[B]

Won'T lend you lending people money. All right, well, we have a very specific circumstance to talk about here today because this is one of my favorite kinds of things that we do here on Help Wanted, which is where we bring on someone who's got a problem, and then you and I try to solve it.

[C]

We give them the help they want.

[B]

It's the help of the help wanted. The helpline is open, and today the caller, the listener, the friend of the show is Jess Chermack, who's been on the show before. Jess, welcome to Help Wanted again.

[D]

Thank you for having me. I'm excited to talk about this.

[B]

Thank you for being here. Jess, you texted me, like, an hour before this recording because you just had this spidey sense that Nicole and I were going to record an episode and you have A interesting quandary to share. What is that? Quandary?

[D]

Yeah. So the quandary. I mean, it's the topic you're talking about, right? Asking people for money. Accept that this is not money that was borrowed and not money that I want or need necessarily. But it's the principle of the matter. I did a nice thing and let a friend borrow a car because we have two cars and my husband was out of town and I cannot drive both at the same time. So a friend was visiting and needed a car. So it seemed like an easy decision.

[B]

Sure. I've let my car to friends before and it feels great, actually, because I got this thing. It's laying around. I don't need it right now. You need it. I'm going to save you some money so you don't have to go to Hertz. Sorry, Hertz. Unless Hertz wants to be a sponsor of the show, in which case, don't go to Hertz.

[D]

It was those other ones. I got the mail this morning and had a fun little notice from the Colorado Transportation Department, whatever that is. A picture. It's actually several pictures of my car on a highway that I have not been on in recent years. Times going that direction. And they're timestamped and date stamped. And essentially what happened was my friend who was using my car violated some traffic laws.

[B]

Oh.

[D]

And there are cameras, apparently, on i25 now in Colorado, and there are pictures of the before, during, and after.

[B]

Oh, my gosh. And there was obviously no way to know this because your friend didn't crash the car. So your friend had borrowed the car and then returned to the car and all seemed totally fine. And this was how long ago?

[D]

A week and a half.

[B]

Okay.

[D]

Yeah.

[B]

And so then flash forward a week. And then it turns out that your friend is actually a reckless driver who was violating all sorts of laws.

[D]

If only. Right. The violation is not. It's kind of nebulous the way that they frame this. It's like a list of things that could have been.

[B]

What?

[D]

Which doesn't mean.

[B]

I mean, there's a lot of things that could have been.

[C]

Yeah.

[B]

The car could have taken off to space.

[C]

Yeah.

[D]

It's strange. So the pictures show that they're potentially. The car might have crossed a double line, which is illegal. So, okay, red flag. It's not like the car is over the double yellow line crossing it. It's just there's this assumption being made because the car at one point was on one side of the road and at another point on the other. And the only space in between, for the most part, was double. Yeah. But then the. So it's a $75 ticket, which is, like, not a lot of money. And at the same time, I don't want to pay it because I wasn't driving. And it's complicated because we have express lanes in Colorado that are technically HOV lanes. If you have more than three people.

[C]

In the car, we don't need to get into traffic.

[D]

This is why it's listed as. There's a traffic violation that costs this amount of money, and one of these things has happened, and that's why you're being fined this amount of money. Okay, well, what happened was she moved lanes point A to point B, was in an express lane at a point where you can't join the express lane, and then got out of the express lane. So my mind, she, like, probably passed a truck or something.

[C]

So she doesn't know this happened. No, to be clear.

[B]

Correct. So the real complication is not traffic law, which. Whatever. The complication is that you got this ticket. Your friend, I assume, does not currently know that you got this ticket, and you don't want to pay this ticket because it wasn't you in the car, but you're feeling weird about asking your friend to pay this ticket. Is that right?

[D]

Yeah. There's a way to contest the ticket, but the contestation is just not worth it. You have to get, like, an affidavit signed by a notary to then submit, and it may or may not be accepted, and it's just not worth it.

[C]

No pass. I'll pay the ticket versus that.

[B]

Just pay the damn thing. So why are you feeling uncomfortable just reaching out to your friend and saying, hey, you violated traffic law. I got a ticket. Here's the ticket. Pay it.

[D]

Good question. And I don't have. I don't have an answer. The psychology of it, I think, is just being a people pleaser and, like, trying to avoid confrontation in general. I'm a woman who was raised in America, which I think this is like a standard narrative here. Like, we.

[B]

I don't know, American women always pay traffic tickets for their friends. That's a. It's a culture.

[C]

No, it's like.

[D]

It's like tab to have confrontational questions with a friend. I think part of it is also that I know the industry she's in. She's in, like, the theater industry.

[B]

She doesn't have any money.

[D]

Yeah. Like, truly. That's, like, part of it.

[B]

Right.

[D]

You know, it's $75. It's at the end of the day, I'm never going to notice that it's gone, but it's taking up mental real estate, and it always will if I pay it without asking the friend to. But also, what if the friend says no?

[C]

What if. Would we want to call her right now or text her together? Do a group?

[D]

That's terrifying. Why?

[C]

No, we could just craft it and maybe she'll respond, and then we can real time, get through it together. You say something basic. Hey. Or take a photo of what you got in the mail. Got this. Ugh. Hidden cameras on the highway.

[D]

Didn't know this was a thing. Cool.

[C]

To send you a Venmo request or something.

[B]

Yeah, well, let's wait before we even get there, Nicole, let's back up and just establish the thing to do. Unquestionably correct. Is that Jess should ask her friend to pay the ticket.

[C]

No, no, no. Otherwise it's going to continue to take up this real estate. The only way to scoot it out of your beautiful, beautiful brain is to get some answers here. There's a lot of what ifs and what if she doesn't pay it? Or what if she's upset? We don't know. We have to ask her. Yeah, we have to say something.

[D]

I think you're right. Which is why I think when I reached out with this predicament an hour ago, it's because I needed to be sitting with the two of you and dragging this thing together.

[B]

That's why I wanted to do it while it was fresh. Yeah. I mean, look, here's a version of this that I lived through and chose a different path that I'm advising for you. The different version of this is that I arranged for two couples to join us out a couple months ago to go to a Broadway show for Jen, my wife's birthday. And it was great. And at the end, everyone was like, tell me how much his tickets were so that I can venmo you. And I said, sure. And then I texted the amount and. And one couple paid and the other didn't. And they. I know that they didn't pay just because they forgot. Right. It's happened to me. You saw it and you're like, oh, I'll take care of that later. And then they didn't. And then I was left with this thing of. Do I nudge them again? Hey, don't forget to pay me. And if I did that, I know that they would pay, and I know that they wouldn't be offended. They wouldn't be like, well, I Thought. I thought you were taking us out for Broadway tickets. But all the same, something held me back from doing it because I just hate hounding friends for money. And so I made this decision, which was to just forget about it. So they got a free night of Broadway on me. And you know what? I don't really. I'm fine with it. I don't really resent it. You know, I enjoyed their company. And I'm sure that they will pay for many things of mine in the future. They probably have. We've gone over to their place for dinner and they've bought lots of food, and so it just all ends up in the wash. But it is for the same reason that you are struggling with this ticket thing, which is that there's just something weirdly uncomfortable about asking friends for money, even if they owe you the money. And that is a strange thing to untie, but.

[C]

Woo. You guys. Do we know how Venmo and Zelle work? There is a request function.

[B]

There is a request function.

[C]

Why can't you just send the request to them? Jason first, then Jesse second?

[B]

You are correct. I totally forgot about that function. I've never used that function.

[C]

Breaking financial.

[B]

Breaking financial news. I've never used it.

[C]

Serious.

[B]

I know it exists. Yeah. I've always just texted people and been like, oh, that thing was $70. And then they Venmo me. So I've never sent the request. But now that I think about it, that would have solved the problem.

[C]

We're going to. Can we do that together?

[B]

Well, no, because it's been so long that I don't even know how much the tickets cost or whatever.

[C]

I'm sure you can.

[D]

It wasn't that long ago, Jason.

[B]

Well, it was. Jen's birthday is in March and it is now August. I feel like that is a long amount of time to randomly be like, hey, remember those Broadway tickets? That then conveys that I am thinking about this on the regular and I.

[C]

Am not literally are right now.

[B]

No. Well, only because of this.

[D]

Only because I. Only because I brought it up. What show was it? Was this a good night and good luck scenario where tickets were $900 to see George Clooney?

[B]

No, it was. What was it? It was great. I had a really good time and I can't.

[D]

Operation.

[B]

It was not Operation Mincemeat.

[D]

It was maybe happy ending.

[B]

No. What the hell was it? What did we see? Oh, wait, we saw. It was smash. We saw smash. And it was great. And I strongly recommend Smash. It was really, really, really funny. And I didn't watch the TV show and I don't really care about Broadway. And it was still really funny. It was money well spent. It was money so well spent that I would pay for another couple, which is what I did. So I'm taking this off the table for me because it's been too long and I think. But I have found peace. I had peace all along. But I am just saying this to acknowledge that there's something weird and very illogical about the discomfort of asking people for money.

[C]

For sure. And that's why this function makes it easier.

[B]

I'm going to do that in the future. But, yes, if you're Jess, then this person.

[D]

Well, okay, look, they don't know about this yet. This is a fresh situation for me and they have no way of knowing because our address is linked to my license plate number.

[B]

Yeah. I mean, I think that if you told her that she got a ticket, she would be mortified and she would instantly want to pay it.

[D]

Yeah, that's so. I think that's the hold up for me. Like, maybe it's less about the money and more the. I don't want her to feel mortified.

[B]

Yeah.

[D]

That's why.

[C]

Let's go back to my suggestion of hey, friend, funny story. Yeah. The worst ate these stupid cameras. You know, they're, you know, all over Colorado. Boo who? And then show her the picture.

[B]

Yeah.

[C]

I think that's commiserate your friends.

[B]

Right.

[C]

First and foremost, like, you're not a bank. That's where these things get tricky. Right. It's the relationship that's front and center. Commiserate. You clearly have some genuine commiseration that you can offer to this context.

[D]

Yeah, yeah.

[C]

And then she'll be like, oh, my God, I'm so sorry.

[D]

How.

[C]

Perhaps she'll say, how much is it? How can I pay you? What's the worst that can happen? Let's use some stoicism.

[D]

That's the thing.

[C]

Yeah. Scenario.

[D]

I love playing worst case scenario.

[C]

Like you. How dare you doctor this.

[B]

Yeah. Yeah. You should have told me that there are cameras there. It's like in the beginning of Back to the Future where Biff. Do you remember this? At the very beginning, Biff is over at McFly's house and he had just totaled McFly's car. And he's like, mcfly, you didn't tell me that your car had a blind spot. In other words, like, biff had borrowed McFly's car and then crashed it. And then his blame McFly on it. That is sort of what would be happening here.

[C]

Yeah. It's like hearkening back to the fake Coldplay thing that we talked about. Like, fakely blaming Chris Martin for this issue.

[B]

Yeah. So this is not Janice's fault. That would be a very unreasonable thing to do. Is your friend unreasonable?

[D]

Not to my knowledge.

[C]

Cool.

[D]

The worst case scenario isn't that they say no. Look, if they say no, I'll just be like, well, that's weird. And I'll pay it. Like, it doesn't matter enough. It's such small nothing to make someone feel bad for even a moment about it, just by the nature of the situation.

[C]

Yeah, but then you're making yourself feel bad, but which is, I think, less good.

[D]

True. And worst case scenario is like the ghosting. Like, what if I send this text and there's just no reply or acknowledgement?

[B]

That would be really weird.

[C]

And do you want a friend like that?

[D]

No.

[B]

Well, then it's time for a friend litmus test. I think Nicole's question right there is like the question, because if you test a friend on something like this and the friend is a real jerk, then that tells you all you need to know about the future former friend. But I also sometimes like to just think, what if everybody had all the information? How would it shake out? And right now, if everybody had all the information, then that would mean that your friend right now is aware that you got this ticket and is also that you're hesitant to reach out. And that, like, you, it's making you feel bad. And if I was the friend, that would make me feel even worse. Not only did I drive your car slightly illegal way, but also I've created this awkward emotional situation for you, and I want to resolve that as fast as possible.

[D]

Possible.

[B]

So that is probably what she's thinking, and she would be mortified about the ticket, but probably mortified that it's a thing that you're spending time feeling bad about.

[C]

You're spending time feeling bad about it. You're on a podcast about it.

[B]

Yeah.

[C]

You're thinking about how to notarize the affidavit or whatever. You're going through a lot. There's a lot of cycles that are happening about this ticket.

[D]

But for what it's worth, I would never have noticed, like, the whole affidavit thing, I. We were doing research, we being, me and my husband, were doing research about it, because it used to be in Colorado that if you got a red light traffic ticket, you could just write a little blurb about how it's not you in the car.

[B]

What?

[D]

They just wave it like it would just disappear. And there's like, entire Reddit threads about this from many years ago, and that's just been. It's been many years since we've been in a situation where a traffic ticket, like, shows up in our mail.

[B]

Okay, wait a second. Stick around. Help Wanted. We'll be right back.

[C]

So, Jason, how did that job search.

[A]

For the social media person go?

[B]

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.

[C]

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

[A]

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

[B]

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

[A]

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 don't have to sit around hoping they notice you. ZipRecruiter gives you a handy invite to apply message so you can nudge your top picks and get their applications. In statistics, four out of five employers who post on ZipRecruiter get a quality candidate within the first day.

[B]

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

[A]

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

[B]

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

[A]

Exactly. ZipRecruiter, the smartest way to hire.

[B]

Welcome back to Help Wanted. Let's get to it. So you got the ticket, you spent some time thinking about it, you did a whole bunch of research on how to get out of traffic tickets, and now you have spent at least 30 minutes on a podcast talking about it. How much time total have you spent on this issue? Brain space plus actual action.

[D]

Like an hour and 45 minutes in the open market.

[B]

How much do you make in an hour and 45 minutes? Like, how much can you do in an hour and 45 minutes to earn?

[C]

I want. Yes. To hire virtual college counselors. Big plug. Go there now, just as the freaking best. How much would I pay you per hour?

[D]

What are your billable hours for undergrad advising? It's 350 an hour.

[B]

So we have lost some serious money here, haven't we?

[D]

Now I feel worse.

[C]

No, that's definitely not the intention. And you are the Coolest. You've done all this research. You found a way to beat the system. Also, it's so satisfying to actually get something that you feel wronged about righted, and it's beyond the value of what your billable hours are. So I get that there's a premium to feeling like justice has been served. I've been living this for the last six months. If I justify the amount of time I spent trying to right some wrongs within the government and otherwise, it wouldn't make zero sense. But then you'll have to add this premium, that there's something that feels wrong about it. And, you know, you could do that with your friend. That could be a cool exercise. Hey, friend. It sucks. Cameras around the highway. The worst. Here's what I got in the mail. Who knew? But also, we could try to dispute it, which maybe we could do together. Or I could give you the information, or we could probably get this taken care of and you do this as a fun, joined friend activity.

[B]

That sounds like a terrible friend activity.

[D]

No, I kind of really like that idea. There is this way to dispute it. It's kind of a pain in the ass.

[C]

But, I mean, there could be the option where you pay it if she says something insane. Jess, you're lying. You doctored this on AI. I never want to talk to you again.

[D]

That hour and 45 minutes was spent on Canva.

[C]

In that case, you pay the ticket and you never talk to this person again. But I think, you know, especially if she's in a precarious financial situation, offering her a solution is a nice friend thing to do. And we need more information after that.

[B]

All right, so are we crafting a text right now that Jess is going to be sending?

[C]

Yes, we should.

[D]

It should involve a photo of this thing, correct?

[B]

Yes, it should involve a photo.

[D]

Okay, I need to go get the thing. I will be right.

[B]

All right.

[D]

Wait, I'm trapped here.

[C]

Okay, we need some sound effects. Insert sound effects. Dear editors.

[B]

Should be like a little vrooming music. Vroom, vroom. He's just drives across the house to get the ticket. You know, I'm trying to put myself in her position. And whether or not I would feel awkward about this, this feels different than the Broadway thing, because the Broadway thing was, like, I voluntarily bought the tickets ahead of time for everybody. I was fine with that. And then we had a great night. This is different. This is. There was a very involuntary situation. And, like, money is clearly owed. Wait, you've got it.

[D]

I do.

[B]

Okay. All right.

[C]

So fresh off.

[B]

Canva that's right, your doctored ticket. Okay. So you're going to take a photo.

[D]

Of the ticket, literally have diagrams of the highway and, like, where the car was.

[B]

It was very detailed. So what are we saying in this text? Hey, friend, got a funny thing in the mail.

[D]

Hilarious.

[C]

Yeah, Colorado, lol.

[B]

Yeah, I like it. Keep it light.

[D]

Can I just start it with. This is super uncomfortable.

[B]

Yeah, you could if you want.

[C]

I mean, depending on what she says. Maybe you could say that, but maybe keep that.

[D]

Keep it to myself. Keep that going confidently.

[C]

Keep that arrow for, you know, I guess.

[B]

Right? That's true. Okay, I take it back. You shouldn't. I'm generally a big fan of, if you're feeling uncomfortable, just tell the person that you're feeling uncomfortable because it, like, defuses the whole thing. But in this case, actually, I think that she would appreciate that you don't think this is a big deal? I kind of like Colorado lol. Because, you know, then you're like, traffic tickets. Everyone gets these stupid traffic tickets. And you got one too. And then it makes her feel less irresponsible with your car to something we haven't talked about. But that perhaps is also tied into this for you, is that you don't want to come across as judgy to her, right? You're like, hey, you are an irresponsible driver, and how dare you cross the double line with my car? So I kind of like being like, hey, Colorado, lol. There are stupid traffic cameras everywhere. This was taken while you were driving my car. I apologize on behalf of the state of Colorado. Do you want to just Venmo me? That's my message.

[C]

Or you can leave it open and see. What does she say after that? Is she like, oh, my God, I'm completely mortified. How do I pay it? Or whatever. Oh, my gosh, that sucks. Or is, oh, my God, Colorado is the worst. Can we dispute this or something? In which case you'll be like, yes, as a matter of fact, this sounds like a fun friend activity to do together. And I have 14 Reddit threads that I have put together, and I've already done associate with my husband because I'm the best. And so I think you just need a response like, where. Where's her head gonna be? And she sees it. And then it's like a choose your own adventure. Do you just do it together? Do you say, like, you know, if she's mortified and, you know, wants to send money, then you send her a request or whatever. You guys send requests. Super Easy. And then it's over.

[B]

All right, Jess, what have you written?

[D]

Okay, so so far I've written, hey.

[B]

Is that like multiple Y's?

[D]

Yeah. Which makes no sense. It really should be multiple E's, but it doesn't look good that way.

[B]

No, no, yeah, it's true.

[D]

Colorado apparently is ridiculous and has installed random cameras on the highway. A fun fact I'm just learning about today. We got a notice of a traffic violation, 75 fine. That's as far as I've gotten. Trying to provide context, maybe, like, you.

[C]

Don'T need that if you just send the picture because that illustrates what you received.

[D]

You know, the picture is kind of like the. This document's kind of hard to read.

[C]

So just maybe say, got this ticket thing in the mail, like, very casual.

[B]

From when you were using the car. Let us be clear, because otherwise she might be like, oh, that's a fun fact that you're sharing with me about Colorado.

[D]

Yeah. Okay. We got this ticket in the mail from when you were borrowing a car. So I have a fractured thumb that looks like a little astronaut in this little. I drew a face on it now.

[B]

So cute.

[D]

I didn't realize how much I actually use both thumbs to text all the time. I'm realizing now.

[B]

You do the swipe text. Yeah, swipe text is amazing.

[C]

Are you stalling?

[D]

No, no, I'm mid sentence. Okay. We got the stick in the mail from when you were borrowing the car. Should I mention anything about. There's ways to. If you want to contest this, there's, like, information on. I don't. How do I end?

[C]

I think you just did. Or would you include the remediation efforts at her disposal?

[B]

No, not to start. Feels like too much.

[D]

It feels so curt. To end with, we got the stick in the mail from when you were borrowing the car.

[C]

How about an emoji? Yeah, a bunch of emojis.

[D]

I always fix everything.

[C]

Like the money car.

[B]

Yeah.

[C]

Our poop car. Perfect.

[B]

This is the point in which you would normally just say, how would you like to pay it? But you don't want to say that because you want to see what she's going to say. So now it leaves it in this weird state. Yeah, I might just go with. I actually might just go with, ack, ack, ack, exclamation mark.

[C]

Yeah. And I mean, look, if she really says, from a genuine place, this is terrible. I haven't gotten a lot of jobs lately, or I'm really struggling and this is going to be rough for me, that's. You Know, you can dispute it together, or you could just pay it for your friend if you want.

[B]

That's true. You're leaving. Open all possible response options.

[D]

Okay.

[C]

And we'll be here.

[B]

Yeah.

[D]

I really shouldn't say anything after that. We got this ticket in the mail for when you were borrowing the car.

[C]

Poop.

[D]

Well, I don't want to. If I put a poop. What if she thinks I'm saying that she is a poop?

[B]

You could be saying that she is.

[C]

A poop monkey with the eyes or like the squiggly mouth one or the.

[B]

No, I think anything. Anything. Seems like it's transfers. We're really overthinking this, which is, I think, indicative of that. There are these kind of weird emotional things here. Unless you just make it as simple as possible and you just say what you've said here, which I think is great so far. Nice, light hearted. But also, here is a traffic ticket I'm going back to. Do you want to just Venmo me?

[C]

Yeah. Or like the collective enemy here is the government, the camera installer people. Right. Like, you're both against whoever that is. Colorado traffic enforcement people. If you're not against her, you're united in. This is annoying.

[D]

F the police.

[B]

Yeah.

[C]

Is there an emoji for that?

[B]

Defund the traffic cameras.

[C]

Okay.

[B]

Yeah.

[D]

No defunding of the traffic cameras.

[B]

All right. Read it back to us one more time.

[D]

Okay. Oh, maybe I. Okay. Hey, good.

[B]

I like the act.

[D]

I'm keeping. I'm keeping that. Colorado is apparently ridiculous and has installed random cameras on the highway. Fun fact. I'm just learning about today. We got this ticket in the mail from when you were borrowing the car. Feel like it needs something.

[B]

How about what would you like to do? Question mark? What a weird. Can I just point out how difficult it is for us to just come up with the right language to just say to the person, pay this ticket. This is validating the core emotional challenge of this question, which is that we can't, the three of us get to the final point of communicating this, because every thing that we come up with either feels like too weird or too pushy or to something when it shouldn't. Because the point of it is that I think she is going to want to pay this ticket and she's going to feel bad that she had caused this ticket and she's going to want you to just tell her, how do I pay the ticket? So that she can rectify the situation again. If everybody had all the knowledge and she knew that this Was all being crafted right now. She would say, oh, my God, Just send the text so that I can respond. Am I right?

[C]

Yeah, yeah, I know. So annoying. Some emoji of your choice. Send.

[D]

There's not even an ask in here.

[B]

Like, there's got to be something at the end of it, and I think it should be.

[D]

If it were me receiving a text like this, I would laugh and probably ignore it or respond with, what, you want me to pay? As a joke? I would respond the way that you're talking, Jason, which is, oh, my God, please send me.

[B]

How?

[D]

Yeah, I don't know that we're.

[B]

Everybody stick around. Help Wanted. We'll be right back. Welcome back to Help Wanted. Let's get to it. I think that we're everybody that we want to be friends with. I don't want to be friends with a person who's like, oh, sure, that is a traffic ticket caused from when I was driving. Get that shit out of my face. That's not somebody I want to be friends with.

[D]

That's fair.

[B]

How is that?

[D]

Yeah, I still think it needs some sort of ask or just, like, something.

[C]

Cool if I send you a Venmo request?

[B]

That's a good one.

[A]

Which was.

[D]

Which you said initially. Yeah.

[B]

Yes. Everything is solved by the request function in Venmo.

[D]

The trauma of it all. Just, like, completely erase that line. Yes.

[B]

Yes. Cool if I send you a Venmo request. Send.

[D]

Okay, wait, I gotta put her in the subject line. I don't put people in the subject line until something's ready to send. If I'm still playing around with it.

[B]

Because I've made mistakes, accidentally hit send. That is a very smart. I actually, I do that whenever I am writing sensitive emails. I will draft the sensitive email without the person in the to field.

[D]

Yes, always. And sometimes when you have a cast on a finger.

[B]

Yeah.

[D]

It's so dumb. It's like a cage.

[B]

It's a cage for your thumb.

[D]

I did. I hit send.

[B]

How do you feel?

[D]

No different, I think.

[C]

No. Well, you just took a big sigh. That's different. You're allowing more oxygen into your fight or flight.

[D]

That's fair. I think I'm the kind of person that now I'm just gonna keep playing worst case scenario. Like, before I send a thing, I'm like, oh, it's just in my head. And now it's.

[B]

Oh, God.

[D]

It's in. In our heads.

[B]

Right.

[D]

So until there's like a response or an acknowledgment or something, which sometimes doesn't come yeah, People.

[B]

Okay, so I just wrote about this, and I will give you the framework that I use, which is that when you are waiting for something and you are imagining a bad outcome, this person hates this thing that I said. I have made this person upset. They're not responding to my text because they don't like me anymore. There are four, count them, four possible explanations for everything at all times. And those are a catastrophic explanation, a bad explanation, a neutral explanation, a good explanation. So in this case, let's say that she doesn't get back to you until tomorrow. All right, well, what are the four outcomes? Catastrophic. She got into a car accident because she's actually a very bad driver and she's in the hospital. That is a catastrophic outcome. Bad. Which is that she saw your text and she's like, jess, I knew that person wouldn't pay a speeding ticket for me. I don't want to be friends with her. What a jerk. Which is a bad outcome, because now you've lost a friend. But also good outcome, because that's a jerk you don't want to be friends with. Neutral, which is that she just didn't see it yet. She missed it, and she hasn't seen it. And so no decision or action has been taken. Or good, which is that she is wiring you money right now and just hasn't arrived yet. And we have to remember that any of those are possible. And so just because you are worried and therefore imagining the bad outcome, which is that she's seen the sex and she hates you now, that doesn't mean that that is the actual thing that's happening. In fact, one of these four things are happening, and it is just as likely that any of the four of them are happening. Catastrophic, bad, neutral, good. So I think that it will be neutral for a while. She will not see it because she is busy memorizing lines for her next theater production. And then eventually, it will be a good outcome in that she will want to venmo you immediately.

[D]

She did respond. It is a good outcome already.

[B]

While I was saying that.

[D]

While you were saying that, I couldn't interrupt because I feel like that's valuable information for all listeners to hear, and I probably just need that, like, on repeat, maybe, as my ringer. If I ever turn to sound on my phone, she says, fucking hysterical. Yes, please send it. I'll pay right now.

[B]

There you go. Boom. Okay, so that really validates your approach in that you made light of it. You weren't judgy, you weren't upset with her. You were Kind of making fun of the situation, but also, you want your $75. And that was all received, and she wanted to send that back to you. Yes, I get it. I definitely owe you that money. Also, this sucks. And I appreciate you. And just send the Venmo request. This is great. Perfect outcome. Yeah.

[D]

Very perfect timing.

[C]

Love it.

[D]

This is one of those things. I don't know why. And I don't think I'm the only person who experiences life this way, but, like, when I'm just, like, sitting, waiting for something, if it's making me super anxious, I'll, like, put that person on. Do not disturb or silence their notifications, because anytime my phone gives a notification of something, I immediately are. Am like, oh, God, I might have to read it. It's like when you go to, like, open that acceptance letter, that might not be an acceptance letter. You know what I mean? Like that.

[B]

Yeah. So as I've talked about on the show before, I was sued, and then this lawsuit went on for five years, and it was awful. And. And so the worst thing about my day was whenever I saw an email from my lawyer in my inbox, because that meant that I had to pay attention to this, and God knows what was going to be in there. And, you know, some. A lot of times nothing. But sometimes it was the bill, which was traumatic to hear about, and sometimes it was an update that the opposing counsel had said something crazy. I just never knew what it was going to be. And so I always feared looking at my inbox because I feared seeing that email. And then for years after that whole thing, I still would occasionally feel anxious looking at my inbox. And I realized that was why, because I was conjuring those moments. So I totally get it. But may this moment right now be the reminder for most people that almost always this works out just fine. You spent a lot of time worrying about this. And actually, the whole thing could have been resolved in about 20 seconds by writing a. Like, a cheeky text and sending it off, and she would have replied 10 seconds later, and it would have all been fine.

[D]

But also, couldn't have done it without you. So it took time and three brains.

[C]

We did it, guys.

[D]

The collective time spent.

[C]

Whoa.

[D]

Thousands of dollars.

[C]

Yeah, we Venmo her for that. We might break Venmo.

[D]

We're taking donations, people.

[C]

I mean, what are you gonna do with the rest of the day now that you have so much brain space?

[D]

Honestly, I have to run 12 miles sometime today or tomorrow, and today's cooler, so I think that's the.

[B]

That's what I'm gonna do.

[D]

It's gonna be so boring.

[B]

Yeah. I think that what you should do.

[D]

Oh, yeah. It's for a marathon. It's not for fun.

[B]

Oh, yeah. That's never for fun. Nobody wants to do that.

[D]

People who say they like running are liars, Every single one of them.

[B]

I think what you should do is just get in the car and change lanes abruptly. See if you get another ticket.

[D]

Try to find all the cameras.

[B]

Yeah, find all the cameras. It'd be a public service.

[D]

Seriously, I should take note of where this is. There's got to be some sort of Reddit thread.

[B]

Yeah.

[D]

To be started. If it hasn't been already saved. Where you can violate laws and where.

[B]

You can't, you can save somebody else $75. But even more importantly, save them at least two hours of time and a podcast appearance. You can do that. That is a public service.

[D]

I'm going to change the world with this.

[B]

$75 at a time.

[C]

One Colorado Venmo request at a time, you guys.

[B]

Yes, it's true.

[C]

Let's go, Venmo.

[D]

We are taking sponsorships.

[B]

Yeah. Venmo and Hertz. Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.

[A]

Pfeiffer, and me, Nicole Lapin. Our executive producer is Morgan Lavoy.

[C]

You want some help?

[A]

Email our helpline@help wantedoneynewsnetwork.com for the chance to have some of 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.

[C]

Maybe a little dance?

[B]

Oh, I didn't sign up for that.

[C]

All right, well, talk to you soon.