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Reddit Story Narrator
So good, so good, so good.
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Andrew (Host of Personal Finance Podcast)
That's why you rack on this episode of the Personal Finance Podcast, we're going to react to crazy Reddit financial situations. What's up everybody and welcome to the perfect Personal Finance podcast. I'm your host, Andrew, founder of MasterMoney Co and today on the Personal Finance podcast, we're gonna be diving into crazy Reddit situations. If you guys have any questions, make sure you join the Master Money newsletter by going to mastermoney.co newsletter. And don't forget to follow us on Spotify, Apple Podcasts, YouTube or whatever podcast player you listen to this podcast on. And if you want to help out the show, consider leaving a five star rating and review on Apple Podcasts, Spotify or your favorite podcast player. Now today we're going to be diving into crazy stories that we found on Reddit. Now this is going to be a really, really fun episode. This is going to be a different style of episode than what we normally do. And so this is going to be one where my wife Irene say hi Irene.
Reddit Story Narrator
Hi.
Andrew (Host of Personal Finance Podcast)
Is going to be reacting to or is going to be reading some of these stories that we found on Reddit. And then what we're going to be doing is diving into these, some of these situations, some of these are crazy relationship situations, some of these are fights with in laws, some of these are even people, you know, cutting off their kids. And so this is going to be one of those episodes that I think you guys are really, really going to enjoy. So we're not going to waste any more time. So without further ado, let's get into it.
Reddit Story Narrator
Am I in the wrong for not lending my boyfriend sixteen hundred dollars to pay his Taxes by next week. Even though I have the money, my boyfriend has been asking me to let him borrow around sixteen hundred dollars for the taxes that he's been needing to pay. Mind you, this is for the October 15th extended deadline. He was supposed to pay this back in March but couldn't afford it so he asked for an IRS extension. I've been reminding him that he needs to save money so he can pay it off, but all he likes to do is spend. On top of that, he's barely making the minimum wage at his job. I have let him borrow money for his rent before four months ago and I have yet to see that money. And he's promised to pay it back, but hasn't. When we go out, I also pay a lot of the times. Because he lives paycheck after paycheck. I am fortunate to have a well paying job and fair savings in my account. It's not the point. He just never listens when it comes to using his money wisely. I am very generous when it comes to money, but when he asked today again, I told him no. He says now that I'm a mean person and I don't care about him and how he will end up in jail if he doesn't pay up. When I've been the only one helping him this whole time. I feel bad because I'm not sure what consequences he will receive. He has been acting pretty dry with me this morning now. So am I in the wrong for not letting him borrow money even though I have it?
Andrew (Host of Personal Finance Podcast)
I want you guys to understand something. Whether it is someone in a relationship or it is someone in your family or a friend who keeps asking you for money. And if you keep giving them money and they don't pay you back, this is just going to be a black hole and it's going to continue to happen over and over and over again. And at some point in time you have to draw a line in the sand and you have to put your foot down unless you're willing to keep giving that person money and not expecting to get it back. And so in this situation, she told him, hey, you need to start saving up for this big tax bill that's coming up every single month. And she can see his spending habits, she can see how he's spending money. He's not prioritizing saving for the tax bill. There's nothing wrong whatsoever with drawing this line in the sand again. So he already owes her rent money. He spends freely without paying any of those bills. He doesn't prioritize his savings or his tax bill. And that's the huge problem. Now saying stuff like I'm gonna go to jail or you're just a mean person. Those are just all guilt trips. They are just deflections trying to get her to give him the money. They are all just different negotiation tactics to make her feel guilty. And so that is something that is a huge red flag. And honestly, huge, huge deal. Now she has the money in her account. This is why she's feeling guilty and why she's wondering about this. But just because you have the money doesn't mean you're obligated to use it or to give it to someone if you don't want to. Now boundaries are also a form of self respect and not cruelty over. And I know people in our lives that get taken advantage of over and over and over again. And if someone guilt you for not funding their irresponsibility, it's a sign that not a one off moment that you need to make sure that you're taking care of it. And so this is just someone who is financially incompetent and really, really important that you make sure that you recognize that red flag in any relationship, whether it's family, friends and or a boyfriend or girlfriend. So leave a comment down below on Spotify or in YouTube and let us know for this first one. What do you think about this and how would you react if someone did this to you? All right, let's jump into number two.
Reddit Story Narrator
Am I in the wrong for telling a woman to charge a guy more at a yard sale?
Andrew (Host of Personal Finance Podcast)
Sale?
Reddit Story Narrator
I was shopping around our city's yard sales yesterday and stopped to look through some clothes. While I was looking, a guy walked up and asked the old lady running the sale if she had anything golf related. My ears perked up because I have just recently gotten into golf. The lady said she had her late husband's clubs but didn't know what they would be worth, so she dragged them out to show the guy. It was obvious the guy knew golf by the way he took a couple practice swings and you could tell by his car and clothing he appeared to be well off. As he looked around the bag, the lady was telling him that her husband had just passed and that she didn't know if the clubs were worth anything. He said they weren't great and offered $200 for everything. She seemed hesitant and she said she didn't know and he just kind of talked over her and said here, I'll go grab the money and and walked towards his car. I walked over to See what was in the bag. And for anyone who knows golf, I'll throw this out there. Almost new GT3 driver, a3 wood, gently used Mizuno irons. Nice titleless wedges. A very nice looking Scotty putter, great condition.
Andrew (Host of Personal Finance Podcast)
And for those who don't know, those are all really good clubs. So they had a really nice driver. They had a Mizuno set of irons which are always very expensive. And then they had a Scotty Cameron putter, which is usually around like $400 just for that putter.
Reddit Story Narrator
The stuff combined would be a steal at a thousand dollars. Obviously, this lady's late husband had spent a good penny on the clubs and I felt bad for her. So I told her she should pass on the guy's offer and have someone at the local courses pro shop help her price out the stuff if she wanted to sell it. She seemed totally shocked when I told her the driver and three wood were probably worth $800 alone. When the guy came back, he was glaring at me. When he tried to hand the lady the cash, she said no thanks and that she was going to get the stuff appraised. He got upset and told her she can't back out of a deal. So I chimed in that they didn't really make a deal. He got mad at me and told me I needed to mind my own business. The lady then told him she wasn't interested again and to please leave. He walked to the end of the driveway and just stood there like my toddler would. Before he walked away, he called me a jerk and stomped off. The whole thing was more funny than anything to me. I was telling this story to my co workers today and they were all dogging on me, saying I should have kept my mouth shut and I should have let the guy get a good deal, but it felt wrong to let him rip her off. So am I in the wrong here?
Andrew (Host of Personal Finance Podcast)
This is a really interesting situation because I have seen people like, there's people who do this for a living. So what they do is they go to different garage sales and they find items and they go and flip those items. And golf is one of those huge items that a lot of people go and look for. So there are people you can find on TikTok or Instagram who actually go out and they'll go try to find value clubs or clubs that make a lot of sense where they'll get them as really good deals. But trying to rip off a widow is a different situation where that person could probably flip those clubs for anywhere from 800 to, to $1,500. And so in that situation, giving someone $200 instead of closer to fair market value I think is a complete ripoff. And so because of this, I don't think he's a jerk whatsoever. Instead, he stepped in because it was a widow, someone who really doesn't know what's going on, you know, who just lost her husband. I think that's a very different situation than buying it from the original owner. If the original owner standing there, he knew what he paid for those clubs and he's willing to give them away for $200, that's one thing. But if it's someone who has no idea what the value is worth, who is just trying to sell some items at their local garage sale, they recently lost their husband and just passed, I think that is a huge, huge ripped off and ensures that he's really not a jerk at all. Now there's a couple of huge takeaways. If you have something like this, like if you have golf clubs in your possession or someone handed you down something and you have no idea what it's worth, go get it appraiser, do some research on those items. And I know for a lot of people who are older, they don't know how to do that research and they don't know how to look on the Internet. But for you, if you're listening right now, most likely because you're listening on a podcast or you're watching on YouTube, that means you know how to go look stuff up. So making sure you get that stuff appraised is really important. Don't skip that step. But also, if your profit depends on someone else's ignorance, that's not clever, that's just shady. And that's not really a business that I want to be in, is just ripping people off and trying to get the lowest possible value on certain people. That's just not a business I really want to run. Some people, they're probably happy doing so, but not something that I'm really interested in. And then sometimes, you know, just stepping in and telling someone that, just trying to help them out, it's not going to hurt you whatsoever. I mean, the guy freaked out, but it's really not going to hurt you long term. And you helped out someone else who could have some extra cash. Do you agree with me or what do you think about that?
Reddit Story Narrator
I definitely agree with you. I think that it's wrong to rip off a widow. And I think that whatever you put out into the world comes back to you. So you should always do the right thing.
Andrew (Host of Personal Finance Podcast)
I agree. Yeah, that's just because of who it was. Like if, again, if it was the original owner, I think that's a different situation. You know, if the guy bought the clubs himself and he's just trying to get him out of his garage, fine. But because it's a widow and she has no idea what the value is, trying to rip her off with 200 bucks, at least get closer to the value. Like if you want to go resell those things, get closer, you know, 500, 700. If you can resell them for, you know, 1400 bucks, then fine. But getting that low of a value is going to be a big deal. Or you can even tell her, hey, these are worth a thousand to twelve hundred bucks. That's what I'm going to go sell them for. Hey, I'll give you 500 bucks for them and kind of give her that information. I think that is the more honest way to do it and saying, hey, this is what I'm going to do with these. I'm going to go resell these. Here's what I'm going to go resell them for. I can pay this amount and still make a profit. And that's how you can have that conversation and be open and honest about it. Let's get into number three.
Reddit Story Narrator
Okay, next one. Am I in the wrong for expecting my boyfriend to pay me back for money I lent him? I, 24, have been with my boyfriend for six years and he is in significant credit card debt and has been trying to pay it off. In the past six months, I have zelled him around $700 whenever he asks for extra money for food. After he dumps his paycheck into paying off his credit card, it would be $300 in one month. A few months later, $200 and last week $100. He tells me he will pay me back after he gets paid, but. But so far he hasn't. Normally I let it go and tell him it's fine, but in my opinion, the borrowing has gotten too frequent for me. Maybe it isn't. In reality, six months pass and nothing. I brought this to his attention and said that it's not about the money itself. It's about you saying you'll pay me back but never do. He was really hurt and disappointed in me, he said, saying how if I were to ask for money, he would just give it to me, no problem and not expect it in return. He also said that he thought I was a person he could really rely on for extra Help. But now he sees that it comes with strings attached and that everyone is in it for themselves. He also said that it wasn't easy asking me for help and he hates doing it Now. I am distraught that he doesn't see me as trustful source of help when he needs it as his girlfriend anymore. I never intended to hurt him or to make him feel bad. I just wanted to establish a boundary for asking for money and a frequency which I thought was too much. I never even wanted the money back. I just thought that he might be taking advantage of it. Am I in the wrong for expecting my boyfriend to pay me back or should I have kept it quiet and let it go?
Andrew (Host of Personal Finance Podcast)
So there is some major manipulation going on right here because she turned a completely reasonable boundary that she put into place where, hey, I lent you some money, you don't pay it back. And so now what? I'm just going to put a boundary line here where I'm not just going to lend you money anymore. And really, you've heard me talk about this before. If you're going to lend somebody money, there's really two options overall. Number one is if you're going to lend them money, you just give them the money, meaning that you don't expect them to pay you back whatsoever. And this is a really, really important concept to understand because here's what happens. Either one, you lend someone money and they don't pay you back and you get upset. Or number two, if you lend someone money, they don't pay you back and then you ask for the money, then you're going to be upset and they're going to be upset at you. Even though you lent them the money, you help them out, but you're putting additional pressure on them. So typically, if you're going to lend somebody money, then you need to make sure that you're just giving them the money. So she was not willing to give him money anymore because she wanted to get it paid back and so she drew a boundary line. Here's a big lesson right here is lending money to someone when you're in a relationship only works if that person either follows through with what the deal was, if they were going to pay you back, then you need to make sure that you are getting paid back. And if you don't, that is going to cause a rift in the relationship. So it can get really, really sticky if you start lending money to someone. Especially when you are dating again. Dating is a much different scenario than when you are married. And if you're expecting the money back. That can really be a huge, huge thing. So a couple of red flags here. Number one is saying, I'll pay you back and never paying back. It doesn't sound like he had any intention to pay her back whatsoever. He was going to keep collecting that money and trying to pay down his debt. Number two is guilt tripping someone when bringing it up. If he. She keeps bringing up the, hey, I want to get paid back. And he starts guilt tripping her and saying, hey, I would never ask you for the money back. Well, the initial conversation was that you were going to pay me back. And so that's. Number two is the guilt tripping. Number three is emotional manipulation to avoid responsibility. So he's manipulating her emotions by saying, hey, I would never ask you for money back. And then number four is using past generosity as a shield for present behavior. Now, this is something I think that you're going to see a lot of people try to deflect and they'll try to push it towards other situations instead of what you were actually having the conversation about. And so you really need to make sure that you recognize these red flags. So a couple of key takeaways that I want you to have from this situation. Number one is money in relationships exposes maturity gaps really fast. You're going to find out a lot about people in relationships when you start bringing up money and there's going to be a huge maturity gap on how people handle money when you start to bring up these situations. Number two is boundaries don't make you cold or selfish. They protect your trust. Meaning overall, it is you trying to put these boundaries in place so that you can continue to trust that person so they don't continue to deceive you. And that's a really big one. Number three, a partner who responds with a fair boundary with a guilt trip is a huge problem. And you need to make sure that you address that problem and or make a decision on what you want to do going forward. And number four is if someone keeps promising something and they never deliver, then they're going to do that in every other area of your life. And so you need to make note of that as time goes on. So when it comes to money, I think this is a huge deal and setting those boundaries was the right move. Let us know in the comments down below on Spotify or YouTube what you think. All right, let's jump into number four.
Reddit Story Narrator
Am I in the wrong by telling my spouse what I don't want to receive on my birthday? My 40th birthday is coming up. My spouse, who's 50ish, has a habit of surprising me with something on my birthday. Which is nice, of course, but in the past years he has gifted me board games and statues of my favorite comic book characters. While I explicitly told him I do not want either of those things reasons, we have plenty of games we still have to play and and we're running out of space to display the figurines. Last year he gifted me a figurine anyway. It was a nice figurine and I liked it. However, I also told him I'd rather had gotten something else instead. Today he asked me what I thought about a specific board game. He thinks I will like to get it for my birthday. I told him I don't want it. It's a board game I'm not interested in and I just don't want any more board games names. He's angry now and calling me very ungrateful and impossible to find gifts for. He's done with this crap. He told me I should just go make a grocery list with stuff that I want then. I do have a wish list by the way. So am I in the wrong?
Andrew (Host of Personal Finance Podcast)
This is hilarious because there's a lot of people that get hurt for some reason when someone tells them what they want. So I am the type of person. I grew up in a family where we told each other what we wanted even when I was younger. When I was a kid, I would give my parents a list and they would say, hey, what are some of the things that you want for Christmas? Because they were tired of buying me things that I really didn't like that much. And so we started just tell each other what we wanted. In fact, we still do that now. We tell each other what we want. Irene and I, we tell each other what we want for gifts when it comes to certain holidays. And a lot of times we buy our own gifts and just hand it to the person to go rap. This is just one of those things where it is actually being financially prudent because you're not wasting money on gifts. That could be something that you're just throwing money out the window because the person doesn't want to tell you that they don't like this item, but they also never use this specific item. So if you're spending your hard earned dollars, I mean you guys work really really hard right now and if you're spending your hard earned dollars on someone else, you want to make sure two things. One, it is money well spent and to the person actually likes and will use the item, whatever it could be. And so really, having one of those lists put together, I think, has helped us a ton. Now, sure, you want to have those spontaneous gifts, and you want to have those gifts of sentimental value, and I think those are really, really cool. But at the same time, you also want to make sure that you are getting the types of things that you actually want, because otherwise you're going to have to go out and buy those things, or you're just not going to be able to afford those things later on down the line. And typically for gifts, it's a time where you get special things that you wouldn't normally buy yourself. And so that's where you can have those lists and put those lists together. What. What do you think? Do you actually like having those lists put together or.
Reddit Story Narrator
I love it. You know how I feel about this. I like telling you what I want. I like when you tell me. I don't think that he should have gotten mad at his spouse for giving him the list. I think that it makes life easier. Sometimes it's one less thing that I can take off my plate because you're telling me exactly what you want. So I like it.
Andrew (Host of Personal Finance Podcast)
And it's setting clear boundaries. It's okay to say what you don't want. It is okay to say, hey, I don't want certain things. And the fact that that guy got mad just means he wanted to just have her affirm something that he wanted to go and buy her. And so really, overall, it's just setting up those, again, boundaries. These relationship ones are. Some of these are ridiculous, like, the way people are reacting, and they really need to kind of hone down or check their emotions, I guess, on some of this. But gift giving could be, you know, a way to build connection. I know some people really are sentimental about some of this stuff, and that's great. I think having sentimental gifts, you know, you want to buy something that can be an heirloom in your family or something like that. I think that's really, really cool. But at the same time, you know, this is a board game. This isn't something that's like, you know, some. Some really fancy, you know, jewelry that somebody worked really hard and they picked it out themselves and they customized it or whatever else. This is something that is just, you know, a game. And so getting mad about that, I think is absolutely crazy. So let me know what you think down in the comments below on Spotify or YouTube. But I think that's absolutely crazy. All right, let's do the next one. Building Credit doesn't have to mean getting into debt With Chime Secured Credit Builder Visa Credit, you can build credit by making everyday purchases and paying them off on time. There's no annual fee, no interest, and no credit check to apply. It's a simple way to work toward a better credit while using your own money and not borrowing it. And since Chime reports to all three major credit bureaus on time, payments can actually help improve your score over time. So if you're looking to build credit the smart way, this is a great place to start. Make everyday purchases count with Chime Secured Credit Builder Visa Credit Card Work on your financial goals through Chime Today. Open an account@chime.compfp that's chime.compfp Chime feels.
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Reddit Story Narrator
Okay, next 1am I in the wrong for setting tuition limit to an in state amount? I male, 51 have two kids, 20 and 17. My 20 year old attends a state university locally and is well within our financial ability. We pay the tuition and fees she commutes. My 17 year old is a high school senior and wants to attend one of several out of state universities. Am I in the wrong for telling him that I will contribute the same amount to his college tuition as I do to his sister and that anything beyond that is his responsibility. Note he has the same ability to attend the local state university and have it paid for. But he wants the out of state and living on campus experience. He is ticked that I won't pay it all off just like I did for his sister. Am I in the wrong and we have some edit? Thanks for the comments. For the record, I definitely did not say I had the money to cover it. I have the funds to cover the tuition and fees of an in state college. I do not have the funds for room and board and the difference in cost for out of state. My son knows this and thinks it's no big deal for me to borrow money so he can attend out of state. He is a good student and will probably get scholarships and I have no problem with him applying out of state. The issue is that if and when he gets in and the scholarships, et cetera leave a balance in excess, what am I supposed to pay without incurring debt? Thanks again all that was an important edit.
Andrew (Host of Personal Finance Podcast)
That's a very important edit and I think I want parents to understand this. Right now you are in no way, shape or form obligated to go into debt so that your kids can go to college. Guess what? You know what you need to be worried about? You need to be worried about your own retirement and we talk about this all the time. If you are not taking care of your own retirement, you should not pay a dime in your kids college. Now we call this the oxygen mask method. What happens when a plane is going down? Well first you put on your own oxygen mask and then you can go and help others. That's what they want you to do. When a plane is going down and crashing and you need to do the same exact thing with your finances. When you are trying to save for retirement, you need to save for your retirement first. And if you don't have the cash on hand for them to go to college, you do not need to take on debt for them to go to college. You need to take care of your retirement and then they can go into debt for their college. Because guess what, if you don't take care of your retirement, you're going to be a huge obligation to your kids later on down the line. You have to take care of your retirement. There's no loans for retirement, there's no bailouts for retirement. So always taking care of that first. I want to say that up front. Now number two, the son is upset because I think up front he thought, you know I'm going to get this fully paid for. I want to go out of state to some of these other expensive schools. But if you haven't looked lately, going out of state instead of in state is a really, really expensive endeavor. In fact, we have people in Master Money Academy who are trying to navigate some stuff like this where they're paying $70,000 for out of state school per year. And so this is a huge financial obligation. And going into hundreds of thousands of dollars worth of debt is never ever worth it for an education. And so establishing boundaries up front, especially when your kids get into high school or before they start high school, saying, hey, I'm going to sit you down right now. If you go to an in state school, I can help support you if that's what you want to do, is going to an in state school. If you go to an out of state school, hey, I can give you as much as I would as at the in state school, but that's about all I can do for you. If you want to go out of state, you're going to have to take on student loans. And so really having this conversation early with your kids can help them as they start to go through school, as they go through testing, as they start to choose colleges, because they're going to know in the back of their head, well, I have to take out student loans, but then also teaching them the gravity of what student loans can actually be on their life. There are people who spend their entire lives paying off student loans and we are seeing student loans at record numbers right now, which is why affordability, one of the reasons why affordability is at an all time low, because most people who are graduating from college have student loans. And so this is a perfect scenario of someone who set boundaries and maybe they should have had the conversations earlier because it seems like not having this conversation means that their son assumed they were going to get the same treatment as the daughter who went to an in state school. And so because of this, they really needed to have those conversations earlier. But now that they are having those conversations, there's nothing wrong with setting those clear expectations and those clear boundaries up front. And so really that's, I think overall, you know what you really need to do. Would you pay for the out of state school?
Reddit Story Narrator
No, I think I would want to be fair amongst both my children. So whatever, whatever I did for the older one, I would do for the second one.
Andrew (Host of Personal Finance Podcast)
Exactly. And I think it's really comes down to just making sure that it is, you know, you're figuring out what that amount is and if they're going out of state. Then you just figure out, okay, I'll pay the difference between the two. But you got to have the money on hand. If you don't have the money on hand, there's nothing you can do because going into debt is not the answer. Especially as you get closer and closer to retirement. We want you to erase debt when you get to retirement. We want you to have a lot of cash on hand. And if you go in deeper into debt just because your kids want to go to an out of state school, that's their choice. That's not your choice. So overall I think that is the way to look at this. But let me know. Are we in the wrong? Let us know down in the comments below on YouTube or on Spotify. All right, let's jump in the next one.
Reddit Story Narrator
Am I in the wrong for asking my future in laws for money? My fiance's parents are loaded. Old money loaded. They can afford what I'm asking no problem. I make very good money at my job. I am currently 27 and earn over a $170,000 a year. Tim is a teacher. He doesn't make as much but he has a trust fund. So he works sort of as a public service. It's big in his family. Recently I had a weird conversation with him and his folks. They think after the wedding I should quit working and be a stay at home mom. I thought they were joking and kind of laugh. They are perfectly serious. They think it's emasculating that I earn more than Tim. Over the course of my career I will earn much more than him. But his trust fund is low seven figures. He could afford to pay me what I earn yearly but he can't due to the stipulations of his trust. His mom on the other hand has lots of interest built up in her trust. So I offered a solution I thought was fair. They set up an unrecoverable trust for me. They must contribute my gross earnings yearly with bumps for anticipated raises and promotions. The deposits would be for the next 35 years. That way I'm a stay at home mom. Tim is the breadwinner and I'm protected in case of a divorce. They went nuts. Apparently I'm ridiculous for thinking they will give me money. I offered a compromise. I signed a prenup wherein I'm entitled to half of Tim's trust in the case of a divorce. And I gave up my career. Also not acceptable to them. I'm kind of at a loss. Do they honestly think I would give up my career with zero Safety net. My mom says I'm being kind of rude for putting everything in such stark monetary terms. I think I'm being reasonable. What do you think?
Andrew (Host of Personal Finance Podcast)
Must be nice to have these problems. So people who came from old money, they just think completely differently. And I think a lot of times they are out of touch with reality, as most of us all know. And really the reality is they're trying to take away someone's ability to earn. And if she wants to go out and earn, and she looks like she earns a very good salary, $170,000 per year, and because she wants to have that ability to earn honestly for their family, if she wants to continue to work, it's going to help their family in the long run be able to invest more money. Having a low seven figure trust fund is really not going to help them long term, depending on where it's invested, unless they really get those dollars working for them and they know what they're doing. And so this is something I think that she is absolutely not in the wrong. Now maybe the way she approached it, asking them for money and asking them to pay her is, is not the right wrong, but them calling her earning more emasculating just shows, you know, kind of where their head and their hearts are. They're in the wrong places big time. And I think overall, you know, they need to change the way that they think about money. They obviously don't understand money because they came from money. And so they have no understanding of even how it works or how it operates. And trying to think of, you know, hierarchy or status as how much you make in a relationship is the wrong way to ever look at money. And so she'd be losing a couple different things. Number one, she'd be losing her earning power. What if that relationship ended, she had no career whatsoever and she's not able to earn money for herself. And so she's trying to negotiate that back in. And maybe those negotiations or those responses are too tough. You could always just say, hey, I'm not, I'm not willing to do that. But negotiating, having, you know, a trust put in her name maybe might not be the best route to take. But at the same time it's worth throwing out there. And so here's a couple of things that I kind of see. They want to control how she lives her life post marriage. And that is something where if you are, you know, an in law or you're someone in a situation, you should have zero say in what somebody does in their career unless they are not Working. Like if you have a spouse, for example, where the. The household needs both people working in order to get by, then you can have a say or just make a comment or something like that. But if it's a situation where they're both working and you want one of them to not work, well, that's a different scenario. Number two is they don't want to back it with legal or financial protection. So they're saying one thing, but they don't want to back it up. So they don't really want that to happen. They just want her to do whatever they want, and that's really a huge, huge red flag. And then number three is she's exposing a huge misalignment in values. If they wanted it to be that way, they probably should have had that conversation prior to the marriage and making sure that happens. And the fact that I don't know where the husband is on this, I don't know if he has stepped in at all, but he really should be stepping in if he's not, and making sure he helps and protects her if that's really what she wants to do in life. And so if someone's trying to take away your financial independence, then you should negotiate protections 100%. And so her trying to negotiate those protections is at least a good first step. It's not really a greedy thing. It's just being smart and making sure you have those protections in place. The red flag really came up when she tried to negotiate in, you know, some sort of prenup where she gets half the trust if they get a divorce or whatever else. That's where the issue kind of stands for me, is that they are not willing to even look into that. And so never, ever, ever let someone guilt you into something when you have set clear boundaries. Do you agree with me?
Reddit Story Narrator
I do. I agree with you 100%. I think it's between the husband and wife and what they do and their future and how they want to raise their family is up to them. And if she wants to have a career, then she should be able to have that career.
Andrew (Host of Personal Finance Podcast)
That's exactly. It's just one of those things that, you know, it's respect versus control, and they're trying to take control of the situation. That's not even their situation. And so overall, if you're marrying into old money or, you know, someone who's marrying into old money, you have to really watch out for some of the values that are with old money, because they don't understand how money works. They don't understand what hard work is and they don't understand some of these specific things. And so you really, really got to watch out for the red flags because they are more persistent in these situations. We've got one more left, so let's do the last one.
Reddit Story Narrator
Another Boyfriend situation Come on ladies. Am I in the wrong for not telling my boyfriend I won money 15 years ago? I don't know what I did wrong or if what I did is wrong and I need some advice. I didn't want to post this on my real account because I'd like to be as anonymous as possible. My boyfriend, 35, and I, 35, were discussing finances as we wanted to be on the same page. My boyfriend moved in with me unexpectedly three months ago as his landlord decided to move into the property with his family. We were discussing finances and the topic of how I own my own place came up. I explained I won some money, not a lot, but enough to be able to put myself through nursing school, purchase my home and have some savings back in 2009 and I bought my place outright and then I rented it until I moved back into it in late 2018. Obviously I had some luck on my side as this was right in the middle of the recession, so I got my place for real cheap. He says I deceived him by giving him the impression that I was financially well off and that I led him to believe that I was more business savvy than I was. I don't know how I did that because I literally work as a nurse, make decent money, fully own my home fully own my car, and have decent retirement plans and decent savings. I'm fairly certain that I am financially better off than most people I know. He says that he can't trust me anymore and that he was stupid to have listened to my financial advice. But the thing is, I never gave him any financial advice except for telling him not to buy a car that was, in my opinion, unreliable and much too expensive. Did I deceive him by not telling him how I got myself financially stable? FYI, we have been dating for almost a year and a half, so this.
Andrew (Host of Personal Finance Podcast)
Is a crazy situation overall because one she owns her house outright, so obviously she made some smart financial decisions just by going forward and kind of taking this money and doing some things with this money to help her future self, but secondarily is that her boyfriend is going to move in unexpectedly into this house that has already paid off and then he feels deceived when he learns that she bought it with luck and not just some of you know, financially savvy, you know, things that she did for saving up or whatever else. Now, deceived is a really strong word here because she never lied. She just didn't lead with the lottery story, which, honestly, when you get started dating, if you lead with something like, hey, I won the lottery and I have all this money, that's a crazy thing to even say to someone. And so there's a huge difference between not disclosing someone and actively deceiving someone going forward. And so there's not a really a trust issue here. It's more about entitlement. It's more about he feels entitled to knowing some of this stuff. Now, here's one thing I want a lot of people out there to note is money will reveal character in a lot of situations. So if you're in a relationship, having money conversations is very, very important. Why? Because it's going to reveal the true character of a lot of people. Money makes people do very weird things. And if you don't have money conversations while you're dating someone, you will not uncover a certain side of them that could be sitting there. And you need to find those red flags early and as early as possible, especially when it comes to relationships. Who you marry is one of the most important financial decisions that you will ever make, because if you are both not on the same page, you will live a life in misery. And I cannot say this enough, you will live a life in misery if you do not marry the right person. So it is very, very important to make sure that you figure this stuff out early and often. Now, there are a bunch of different financial red flags here, and there are tons of them that I think a lot of people need to know. Number one, is getting mad at not having access to your assets. That is something that is just absolutely crazy, especially when you're dating. And if you're not married, you have zero right to any of their money whatsoever. So this is something that I think most people need to note is a lot of people are dating and they feel like, you know, we can commingle funds or we can do all these different things. No, you have to be married before you can even do some of that stuff. There was also an edit in this post that claimed that he said he could invest better than she could, and they would have had way more money if she would have actually given him access to this money. This is another huge thing where he should not have that access to this money whatsoever. This is her money. They are still dating. So there's a Couple of things I want a lot of people to think through here. If you want to have healthy money conversations, money conversations around money that you need to make sure that you have how can we align on goals and expenses is number one, that's part of the conversation that you need to have is how do you figure out what your goals are and how do you align on those goals? Then why didn't you tell me you had money? Plus, buy me a car is completely unhealthy. So what's unhealthy is saying something like, why didn't you tell me you had money? Now, sure, being open and honest and having those open conversations when you get further down the relationship, completely agree. But getting upset and angry about this because you wanted access to those funds, that's a big, big red flag. So here's some key takeaways that I want you guys to have. You don't owe anyone your full financial history early on in a relationship. Now, if you want to ask somebody outright, hey, do you have debt? And if they say no and they actually do have a lot of debt, sure, that's a red flag. If you ask that question and someone is open and honest with you about what the situation is, that's completely fine. But she did not mislead him whatsoever. Number two is watch how people react to your wins, because this is a very interesting reaction to finding out that she won money. And in someone's winning, watch how they react to your wins, not just your struggles. And don't ignore early red flags with money. I cannot stress this enough. If you see a lot of red flags on the way a person reacts with money is going to get a lot, lot worse later on in the relationship. And so that is something you definitely want to make sure that you note. Well, that's the last one we have for today. If you guys enjoyed this episode, leave a comment down below or shoot me an email. These are kind of fun to make and so we can keep doing these type of episodes because there are a ton more situations just like this. And if you want us to react to anything else, send them in my way and you can send them to andrewastermoney Co that way as well. Also, if you want help from me, if you want direct help from me, join Master Money Academy. If you go to MasterMoney Co join. That is the place where you can get direct help from me. Irene is also in there and she helps with Master Money Academy and the rest of our team is also in there as well. So really, really appreciate you guys who are in Master Money Academy. We are seeing some cool transformations, some amazing, amazing stuff in there. And we have a new course that just dropped in Master Money Academy. If you haven't checked that out yet already, make sure you check it out. It's automate your money in one weekend. And this is literally a five video course that teaches you to automate your money and in one weekend. But if you also want access to that, we'll leave a link down in the show notes below. You can buy it Alakart as well. Listen, thank you again for joining us here on the personal finance podcast. We really, really appreciate you being here and we'll see you on the next episode.
Episode: Money Expert Reacts to INSANE Reddit Finance Posts (AITA)
Host: Andrew Giancola
Guest/Co-Host: Irene
Date: November 19, 2025
In this lively and insightful episode, Andrew Giancola dives headfirst into some of the wildest and most contentious personal finance stories sourced from Reddit’s "Am I The A**hole?" (AITA) community. Joined by his wife Irene, the duo reads and reacts to a series of real-life financial dilemmas—ranging from entangled romantic money issues to family and inheritance trouble. With sharp analysis, actionable takeaways, and relatable commentary, Andrew breaks down the dos and don’ts of handling money matters with loved ones.
[02:37 – 06:03]
Reddit Scenario:
A woman refuses to lend her boyfriend $1,600 for overdue taxes after having already lent him rent money (never repaid) and regularly paying when they go out. He calls her "mean" and says she doesn't care about him.
Andrew’s Insights:
Memorable Quote:
“If someone guilt you for not funding their irresponsibility, it's a sign—not a one-off moment—that you need to make sure that you're taking care of.”
— Andrew (05:01)
[06:03 – 11:55]
Reddit Scenario:
A shopper at a yard sale advises a widow to reject a lowball $200 offer for valuable golf clubs, angering the would-be buyer but sparing her a big financial loss.
Andrew’s Insights:
Memorable Quotes:
“But trying to rip off a widow is a different situation.”
— Andrew (08:55)
“If your profit depends on someone else’s ignorance, that’s not clever, that’s just shady.”
— Andrew (09:32)
[11:55 – 17:26]
Reddit Scenario:
A woman regularly loans her boyfriend money (for food, etc.) as he pays off his credit card debt, but he never repays her. When she sets a boundary, he accuses her of being selfish.
Andrew’s Insights:
Key Takeaways:
Memorable Quote:
“Money in relationships exposes maturity gaps really fast... Boundaries don't make you cold or selfish, they protect your trust.”
— Andrew (15:24)
[17:26 – 20:38]
Reddit Scenario:
A woman asks her spouse not to buy her more board games/statues for her 40th birthday, but he takes offense and calls her ungrateful.
Andrew & Irene's Insights:
Memorable Moments:
“Sometimes it's one less thing that I can take off my plate because you're telling me exactly what you want. So I like it.”
— Irene (20:18)
[25:31 – 30:24]
Reddit Scenario:
A father tells his son he’ll pay for in-state college tuition but not more expensive out-of-state costs, which upsets the son.
Andrew’s Insights:
Memorable Quote:
“If you are not taking care of your own retirement, you should not pay a dime in your kids' college. Now we call this the oxygen mask method.”
— Andrew (27:23)
[31:01 – 36:39]
Reddit Scenario:
A high-earning woman is asked by her fiancé’s wealthy family to quit her job and be a stay-at-home mom, but they refuse her requests for legal or financial safeguards. She proposes a trust or prenup—sparking outrage.
Andrew’s Insights:
Memorable Quote:
“They want to control how she lives her life post marriage… That is something where, if you are, you know, an in law or you're someone in a situation, you should have zero say in what somebody does in their career unless they are not working.”
— Andrew (33:40)
[37:09 – End]
Reddit Scenario:
A woman’s boyfriend feels “deceived” after learning she paid off her house with lottery winnings instead of by “business savvy.” He questions her trustworthiness and advice.
Andrew’s Insights:
Key Takeaways:
Memorable Quote:
“If you're not married, you have zero right to any of their money whatsoever… Getting mad at not having access to your assets is just absolutely crazy, especially when you're dating.”
— Andrew (39:32)
Andrew frequently encourages audience feedback and comments, particularly on contentious or relatable scenarios.
“Let us know in the comments down below on Spotify or YouTube what you think…” (Multiple segments)
This episode mixes sharp personal finance advice with practical relationship wisdom, all delivered in an approachable, conversational tone. The key thread is that boundaries, honesty, and education are essential for preventing money from ruining your closest relationships—no matter how wild the scenario.