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This Is Uncomfortable

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Feb 12, 2026

Help! My dad is dating a scammer!

Advice on money and dating, featuring radio and podcast host Sam Sanders

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Radio and podcast host Sam Sanders
Radio and podcast host Sam Sanders
Photo credit: Rommel Alcantara

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Dating and money drama go together like dinner and a movie. A few weeks ago, we asked for your questions about money and dating and you delivered. Joining us to answer your questions is Sam Sanders (host of KCRW’s “The Sam Sanders Show”), who has hot takes and sage advice on everything from secret investments to dating a scammer.

If you have any money drama going on in your relationships and want advice, we want to help! You can send it to us at uncomfortable@marketplace.org, leave a message at 347-RING-TIU, or fill out the form at the bottom of the page.

Reema and producer Alice Wilder shared some listener questions with Sam, and here’s his advice (lightly edited for clarity and length):

  • Question 1: “My dad, who's 60, met a 21-year-old passenger while driving for Uber. She told him she was homeless, so he started paying for her hotel, helped her get a job, bought her a car, and in total he's hemorrhaged about $20,000 in about two months.He's borrowing money that he doesn't have, and everyone around him is telling him that she's using him. She tells him that everyone is just jealous or dislikes her, but he's convinced she's the real deal. He even got a tattoo of her name. How do I make him see that she's probably scamming him, or do I just have to let him learn the hard way?” – Witness to a Scam

Sam Sanders: I am at the age where a lot of my friends are dealing with parents who are older and susceptible to getting scammed. So don't spiral, because this happens frequently to lots of people, and you aren't the first to deal with this. Think about where your father will accept the most feedback and from whom. A lot of times people don't want to hear the right thing to do from their kid, because it's weird for a kid to exert authority or expertise over them. So is there someone else involved in your father's life, family or friend who can do that for you?

Reema Khrais: Yeah. It feels like one of those situations where you really have to wait for the person to wake up. It's really hard to logic someone out of an emotional situation. Especially in the case where, essentially, he is trading money for a feeling that he's probably craving – a need to feel relevant or young again, or chosen or whatever. And so, they’re in this loop where they’re giving more money and that's creating a sense of closeness, which justifies more money. And the only way it usually ends is when they're like financially wiped out. You can ask questions that kind of force him to name the reality that he's in, such as: How much of your retirement or debt have you touched? What are you gonna do six months from now if she's still asking you for money?

Sanders: When you're dealing with this, people who are close to you and are being financially irresponsible, half the work is trying to help them through it, but the other half is keeping your own peace in the midst of it. When you see a parent going through this and letting go of their life savings, it can very easily drive you into a state of frenzy or spiral. You have to not let that happen to you because you won't be able to help them if you're spiraling yourself. You can't yell at them until they figure it out, and you can't blame yourself. I have told people all the time, when you are experiencing an adult in your life who is acting like a child, that is the time at which you most need to be an adult.

The “Uncomfortable” verdict: Witness to a Scam, you’re dealing with a complex and infuriating situation. If you can, keep your cool, ask him questions about his relationship and let him know that you’ll be there to support him if he decides to leave the relationship. But ultimately, you can’t control what another adult does with their money. Seek out support from your loved ones and keep taking care of yourself.

  • Question 2: “I'm queer and poly and have been dating a man who makes at least three times as much as me. For a while, he paid for everything on our dates, which I really appreciated since I don't make a ton of money. Then he went on a big expensive vacation with his primary partner. Ever since, he stopped paying for things on dates, and he even Venmo requested me for half a pizza after saying he would pick it up for us. Is it weird if I bring this up with him?” – Secondary Partner

Sanders: Blessings to everyone poly who is listening to this, but I'm just gonna say from my own point of view, when you start to get into the space of primaries and secondaries and that's messy. And I think that the problem with some of these relationships is that once the hierarchy is set, nothing else is set. So there probably was never a grounding conversation about how money needs to work in the relationship, because had there been, he would've had to talk to you first before this total switch up.

Alice Wilder: A lot of my friends are poly and I think it’s important to remember that you're not less than just because you're not, you don't live with this person, you're not legally married. You still can advocate for yourself in these situations or be like, “Hey, this feels a little weird. Like, I don't really know what the solution is, but it feels kind of weird to me. Let's talk about it.”

Khrais: Otherwise, like money is quietly demoting you or it's like setting up that ranking. And I think even if they're not in a poly relationship, it is worth talking about, because implicitly this person was saying, “I have more money so I will cover things. Don't worry about it,” which creates a sense of care and security. And now because he's pulling back his spending, I can imagine the listener feels like he's not as valued or not in the same category as the primary partner. So I think you can say, “I noticed something changed after the trip and it changed how secure I'm feeling, and I just wanna get a sense of where you're at.”

Sanders: Yeah. And not to bash anyone in poly relationships, because most non-poly relationships don't have these conversations either. I think you really should have a conversation about how the money is working there, because it's not just money anymore – it's emotional, and it is signaling something about your relationship. There's a way to bring it up that is not accusatory, that is not forcing an ultimatum: just say very casually and quickly, “I am trying to spend less money these days. I would love for us to pick some kind of activity that is pretty cheap or free.” And just see what they say, and that might open up the doors of the conversation. Make it an “I” conversation: “I'm spending less money right now, so how can we accommodate that?”

The “Uncomfortable” verdict: So Secondary Partner, no matter your relationship structure, you should be able to have candid conversations about money. Start from a nonjudgemental place, and see how your partner responds. It could be that the conversation becomes less about money, and more about how they do… or don’t make you feel valued.

  • Question 3: “I've been with my fiance for three years, and we're stuck on where to build our life. We both grew up in the same big city, and our families are here. But he works in a niche industry where the best jobs are a two-hour flight away, in a city where we don't know anyone. I've been clear that I don't want to leave. Even thinking about moving makes me panic, and it almost broke us up last year. If he can’t find something good paying here, moving feels inevitable. I’m really torn - I’d rather stay put, even if that means we make less money, but at the same time, I don’t want him to feel stunted in his career and resent me. What should I do?” – Move Out or Move On

Sanders: Resentment will end a relationship. And so if you're already worried about resentment, that means it's a serious issue that needs to be taken seriously. I hate to say my advice is to break up, but if you can't budge and they can't budge and you aren't aligned, then where do both of you see yourselves in 10 years? And how closely are you wedded to that vision and version of your life? If you're really tied to being where you are and you don't want to change that, having to move will make you resent him. If he's really tied to moving and you make him stay, it'll make him resent you, and resentment will end the relationship. So if you can't find something that will lead to neither of you having resentment over this, it might be worth considering ending the relationship.

Khrais: You need to have an open conversation, and again, you want to ground it in “I” statements: you're not saying, “your career is not important,” but rather “I'm really scared of losing my support system here and my sense of home and my friends and family and everything that makes my life feel like my life.” And he's probably afraid of not advancing his career. I think those are both very real fears.  You can fall into the trap of feeling like it's a negotiation, when really it's a conversation probably about your values and what you're willing to do. And also I think it's easy to think that something like this will be forever, but it might not be. You can always go into something with an agreement, like this is an experiment.

Sanders: Yeah, maybe there's a scenario in which you both just put a timeline on it: “We’ll try this out, but if at year three or four or five, it still does not work, we're gonna move somewhere else or move back.” If that were a part of the conversation, it might help both of you feel like you were getting something out of this arrangement.

The “Uncomfortable” verdict: Move Out or Move On, this doesn’t have to be a make or break for your relationship. But you should both sit down and consider where you see yourselves in the next five years and how flexible you can be about those plans. Preventing resentment is the name of the game, so make sure you are honest with yourself and your partner about what you’re willing to accept.

  • Question 4: “The guy I'm dating financially supports his family, and I know he's in a lot of debt. At the same time, he insists on paying for everything. For example, we recently went to see a movie together, and since I got to the theater before him, I got our tickets and a couple of sodas. He insisted on buying two more sodas because he couldn't accept that he wasn't paying for the date. I make a good living and would love to split expenses more evenly. Part of this is cultural: we're both Arab and I don't wanna embarrass him by citing his debt as a reason for us to split things, but I also don't want dating me to make his financial situation even worse.” – Dating Debt

Sanders: I think that there are some red flags for me. If this guy is not just supporting his family to the point where he's going into debt, but also paying a second time for things you've already paid for, I think there's some larger, deep-seated issues around money here that haven't really been unpacked. And I think that there's a lot of maybe male-centric pride that needs to be addressed, but if he can't address it, I'd say run for the doors.

Khrais: Honestly, this hits pretty close to home as an Arab American myself. I feel like I've been in this situation before. In Arab cultures, speaking very generally, there is a strong expectation that the man in a heterosexual relationship will provide financially. And so it can feel shameful to show up metaphorically empty-handed when you're dating or courting someone. Money and masculinity are very interwoven, and what he did was beyond just like a nice gesture. It was a very strong way of saying no.

Sanders: It's a sign of dominance… And it's not helping the future of their relationship as a couple. He's not building the foundation of y'all's relationship if he's already wasting money to speak to his pride.

Khrais: If this is early in their relationships, then maybe this is his way of trying to court her. But if it becomes a pattern, then make the conversation about partnership and not pity. Don’t go to him and say, “Hey, you're in debt, so stop paying so much.” Instead try saying, “Hey, I want to feel like this is a meaningful partnership, so I want to contribute and show my care that way. It makes me feel closer to you.”

Sanders: Yeah, look for and see if he can make progress on this, if he can communicate about the problem effectively and speak to his emotions and find a solution and a way forward. If he can have a good and substantive conversation with you in this moment about pride and money, you're on the right track. But if he can't have a conversation about this, what else will he not be able to have a conversation with you about? It's less about the money and more about the communication: can this guy communicate with you in the way that you need to feel supported in a relationship?

The “Uncomfortable” verdict: Dating Debt, it sounds like it’s still early days with this guy, which means it’s the perfect time to figure out whether he can have a vulnerable conversation about money. If he’s not able to set aside his pride and let you contribute financially to dates, then maybe you should start going to the movies with friends, instead.

  • Question 5: I recently overheard a conversation between my long-term girlfriend and her mom, where they were speculating about whether or not I knew that my girlfriend had over $50,000 invested in oil. I did not know this. I've been struggling to get by and had no idea she had that much money to invest in anything, let alone oil. I'm pretty progressive and care deeply about climate change as an issue. I understand it's impossible to be fully divested from fossil fuels, but 50K is a pretty major investment. It's her money, but it does seem to reveal a big difference in our values. Should I bring this up to her?” Divest from Dating

Sanders: Are you mad about the oil investment or are you mad about your partner not sharing 50K with you? It seems like you need to have a conversation with yourself before you make it a conversation with your partner, because what I would hate for you to do is hide your complex emotions about money and sharing under a certain kind of performative progressivism in which it's all about the oil and divesting. So think about what's really at play in this issue for you before you talk to your partner. And then besides that, I don't know, call me old school: if y'all aren't married, then how they invest their money is their business.

Khrais: I want to push back here because I think you're right to some degree, what someone does with their money while they're dating is their money, but on the other hand, if you're trying to build a family together, then you want to be morally and financially aligned, if that's what the intention is.

Sanders: Oh, for sure. I think if this were less than a year and we still weren't too serious yet and hadn't talked about making plans for a future, I'd leave it alone. If you're building a life with this person and see yourself living together, being married, having kids, then it's for sure worth talking about. But I would not do the thing where I make the conversation all about one's politics. It's about much more than that, and it's much more emotional than that. So be sure that you're being clear about what you want out of all of this.

Khrais: You can approach it by saying, “I overheard something that really surprised me, didn't realize you had that money invested, but it also makes me feel like I don't actually understand your financial world or how you think about what matters. So can we talk about that?”

Sanders: Exactly. It seems like they think the partner had a responsibility to share not only that the money existed, but also how it's invested, and that requires a conversation about what the expectations are of this relationship, because this partner might have a different expectation. So expectation and level setting is really important in this moment too, I think.

Wilder: My partner and I talk about which stores we shop at and which ones we don't, or which products we feel good about buying and which ones we don't. And I think if I found out someone who I'd been with long term was investing in something and actively keeping it a secret that I was really morally opposed to, then I would feel a type of way.

The “Uncomfortable” verdict: Divest from Dating, you and your girlfriend aren’t married so she’s not obligated to share her financial life with you…but there’s a difference between filling up your car and actively investing tens of thousands of dollars in the fossil fuel industry. And if she’s keeping that a secret from you, that’s a red flag. The two of you should have a candid, non-judgmental conversation about your values.


If you liked this episode, share it with a friend. And if you want to tell us what you thought about our advice or have a question of your own, email us at uncomfortable@marketplace.org or fill out the form below.









The Team