Tiger Sisters - How to Talk About Money With Your Partner

Episode Date: November 10, 2025

💬 You earn more than your boyfriend. Your work bestie’s acting weird after your promotion. And your boss just commented “🔥” on your vacation pic.In this unfiltered Tiger Sisters Hotline ep...isode, Jean and Cherie take on your real-life dilemmas about money, power, and love… from splitting expenses with a partner to navigating awkward office politics. Honest advice, real strategy, and a lots of sisterly tough love.We share: ✅ What to do when your work bestie turns cold after your promotion ✅ How to handle overfriendly bosses on social media ✅ The red flags in love and friendship when money becomes transactional ✅ How to talk about money with your partner (without making it awkward)✅ When to split fairly vs. evenly — and why fairness isn’t always 50/50 ✅ Why every relationship needs an operating system🐯👯‍♀️ We’re the Tiger Sisters — Your Wall Street & Silicon Valley big sistersDecoding Money • Power • Love✨ New episodes every Monday | Shorts all week ✨🎯 This episode is sponsored by OneSkin: Get 15% off OneSkin with the code TIGERSISTERS at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.oneskin.co #oneskinpod💌 Want to partner with us? Sponsorships: partnerships@tigersisters.co⏰ Timestamps00:00 Welcome to the Tiger Sisters Hotline00:55 Spotify Radar and rebrand glow-up03:14 Dilemma #1: I make more than my boyfriend — should I pay more rent?04:10 How to talk about money minus the awkwardness07:44 The $10,000 thought experiment10:46 Why you need an “operating system” for your relationship14:00 The 70/30 rent rule and what actually feels fair16:18 Ad Break: OneSkin17:47 Dilemma #2: I got promoted over my work bestie — now it’s awkward19:24 Leading with compassion and when to escalate23:47 Dilemma #3: My boss comments on all my Instagram posts25:04 Setting social media boundaries at work27:02 Dilemma #4:: My boyfriend Venmo's me for everything30:43 Cherie’s $2.80 water-bottle story32:36 Transactional vs. generous relationships34:00 The “standard deviation” theory of compatibility35:57 Wrap-up 👀 Newsletter: https://cherieluo.substack.com/Why trust us?▫️ Cherie Brooke Luo – 100M+ views demystifying big tech, finance & MBAs▫️ Jean Luo – ex-Goldman, ex-Snapchat exec, 50+ AI patents, startup investor▫️ Together: 4 Ivy degrees • built billion-dollar products • two startups — decoded for youWhat you’ll get (and keep):▫️ 🚀 Ivy League cheat sheets – no $250K tuition required▫️ Personal finance playbooks – salary jumps, investing, money psychology▫️ Networking scripts – behind $100M+ deals, job offers & VC intros▫️ Real talk with unicorn founders, VCs, and billionaires▫️ Mindset resets – clarity minus the pricey life coach▫️ Lifestyle, wellness, and productivity hacks that actually work💛 LET'S CONNECT:~ CHERIE ~🤳🏻 Instagram – / cherie.brooke📱 TikTok – / cherie.brooke✍🏻 Substack – cherieluo.substack.com👩🏻‍💻 LinkedIn – / cherie-luo~ JEAN ~🤳🏻 Instagram – / jeanluo_👩🏻‍💻 LinkedIn – / jeanluo👉 Hit Subscribe & tap the 🔔, then WRITE A REVIEW and rate us ⭐️⭐️⭐️⭐️⭐️ on Spotify & Apple Podcasts!Share this with someone who deserves to be seen as a leader.🎵 Music: Sammy Signal – https://open.spotify.com/artist/2HsyknHuxhT8RoZfn5rqMS 🛍️ Items: 🍵 Sisters Matcha – www.sistersmatcha.com🌀 Everything else – https://amzn.to/3z0dx5b

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Starting point is 00:00:00 What do you do when you make more money than your boyfriend and you're about to move in together? Or you get promoted over your work bestie and they start acting weird. What if you move across the country for a dream job and then you realize that you hate it? Welcome to the Tiger Sisters Hotline where we solve all of your problems about money, power, and love. We're sisters, we went to Harvard and Stanford's Business School and today we're going to give you the advice, the things that your friends won't tell you and the things that HR legally cannot tell you. We asked our listeners to send in their real-life dilemmas, and today's batch is so good. It's actually the first time we're doing this, so we are so excited to dig into these questions. But before we dive in, let's do a quick update.
Starting point is 00:00:47 Jean and I have been on the move, on the go, go, go for the last week. And so, Gene, what has been your favorite thing over the last seven days? Yeah, so, okay, you guys might notice we're in a different studio. We're actually in the Spotify studio in New York City. And the reason we're here is because we just launched season six, and we were announced as spotting Radar 2025. Yay! Yay!
Starting point is 00:01:08 And my favorite part of all of this was doing our big rebranding exercise and coming out to the world and like having a whole new cover photo and showing everyone, like kind of like showing up in the world the way that we see ourselves finally. And my favorite part of that was this photo shoot that we did at the Albright Fashion Library, which is in L.A. There's also one in New York where we got to dress up in these amazing outfits that were all on theme with our rebrand. And it was just the most incredible experience. Like I felt like we were like real-life Barbies in the best way. So shout out to Irene Albright and the Albright Fashion Library for hosting us there and for basically making our dreams come true.
Starting point is 00:01:56 Yeah. If you guys haven't seen it, it is our new rebrand. We have a new visual identity. It's on all the platforms and we have a new cover art, new typography, new everything. And I feel like we were so lucky to work with so many creative geniuses throughout the entire process. I have a newfound appreciation and like respect for people who work in creative fields because Gene and I have this vision of Tiger Sisters of where we want to go. And obviously there's a gap between like where we want to go and where we are today. And the creatives that we've worked with over the last, honestly, like month plus are just like absolute geniuses, you know, in bringing our like vision to life and helping us have this new visual identity.
Starting point is 00:02:44 Because we've always kind of felt like our cover photo, we felt like our like boss-ass bitch photo shoot, but we've just never had a way to implement it. And I'm just so thankful for the support that we've had in bringing this to life. It's amazing. So check it out if you haven't seen it already. Okay. our first question is so juicy. I really love it. We've actually seen a bunch of questions come in that are pretty similar. And I love it because it's about money, power, and love. The trifecta altogether. Yeah. Okay. So, Shrew, why don't you read it? Okay. So the first question is about money and moving in. So it goes, dear tiger sisters, my boyfriend and I are moving in together. I make more money than him and want to talk about money. How do I bring it up without making it weird? And should I pay more rent? I have a sense that I make significantly more than him. He's a teacher and I work in digital advertising slash tech, but I don't have a sense
Starting point is 00:03:35 of his larger financial picture, like how he saves for retirement and what his goals are. Do you have any advice about how to initiate the conversation? What questions should I ask? Also, should I offer to pay more rent and household expenses because I make more or should I just let him pay half? Because that's what we do when we travel or go out. Okay, well, thank you for this question. It's super juicy and I know many of our listeners probably have the same question or are in the same stage of their life. This question is so relevant because the number one reason that couples fight is about money. Yeah. I mean, it can feel unromantic to talk about finances, but it's actually probably one of the most important conversations you're going to have if you're going to take the
Starting point is 00:04:19 next step and actually move in with someone. Yeah, I think the number one thing is just to initiate the conversation. Just have the conversation. So just be neutral and like natural. Like don't be awkward. Awkward about it. Because it's not awkward. Yeah, it's not awkward. It's actually something that's like we have to talk about it. So just be like, hey, I'd love to talk about our finances. Let's find a time and let's sit down together. Maybe open up a bottle of wine. I would recommend doing this in a setting that you feel most comfortable. Like I wouldn't do it if you're like out on a date in public at a dinner spot like that or at a restaurant. Like I. Like, I wouldn't do that, but I would do it like if you guys are having like a cozy night in or you can like have more privacy.
Starting point is 00:05:01 So you can actually dig into, you know, some of the conversation and potentially pull up your banking apps to actually like, you know, talk through things. Doing it at a restaurant is like it's too much going on. No, don't do that. It's very public. So do it in like a cozy comfortable setting, maybe in pajamas. Like I feel like, yeah, have a bottle or a glass of wine or a LaCroix. Cozy Earth pajamas? and make it very like comfortable.
Starting point is 00:05:27 We recommend that you hit three questions when you have this conversation. Don't just talk about, you know, like how much do you make? You should ask, what is your approach to saving and spending? First question. Second question, you should ask about how do you budget or do you even budget? Like, is that something that you do in your everyday life? And how many times do you even think about and approach your money? Yeah.
Starting point is 00:05:49 And the third thing to think about is what are your long-term goals? So asking your partner what their goals. what their goals are and long-term thinking is around retirement, do they want to buy a house, or do they just want to have a huge travel fund because that's the number one thing that they care about? Yeah, I love those as like topic areas. And there are two questions that I would recommend asking. The first one is also just like exploratory and trying to learn more about your partner's values when it comes to money. And so like asking them about how they grew up, like how did your family talk about money growing up or like was it a topic that you guys you know even discussed or was it
Starting point is 00:06:28 something that's more taboo so you want to turn it into a therapy session kind of but also that's like me you know like I'm more philosophical and I'm like seeking to understand you know like because sometimes like honestly it can be kind of awkward to like launch into these things so like if you ask them questions about how they grew up in a way to better understand them and what they care about it can be a launching pad to some of these other questions that are more tactical. Like, be like, how did your family, like, think about money growing up? And then, like, a follow-up question can be about budgeting. Yeah.
Starting point is 00:07:01 Or like, yeah, did you do budgeting? Or, like, and then now it's like, how do you do budgeting? I mean, I think that makes sense. I just think that just be careful to make sure that you're not the one that feels, like, responsible for driving the entire conversation. Like, I think it's fine if you're the one that's initiating it. But you should see that your partner is. also, you know, once you've initiated the conversation, they are engaging at least 50-50,
Starting point is 00:07:27 and they are actively wanting to participate in and continue and develop and evolve the conversation instead of being avoidant about it. Yeah, they should also be curious about your answers as well, not just like it being one-sided. And the second question that I like, that is a way to, you know, bridge the gap into some of these more tactical questions. is actually we heard our friend, Rameet Sathy, say this, and I love it because it's also a bit philosophical, but, like, it doesn't, it's like a serious topic, but then if you go philosophical, it doesn't feel as serious or, like, awkward. Okay.
Starting point is 00:08:03 So, like, the question Rameet Sathy, like, says to ask, and I've done this before, is, like, if you were to get $10,000 tomorrow, like, how would you spend it together and see where you guys align? Because I think to your third question, your third point, on, like, what are your long-term goals, travel, house, or retirement. Like, this is a good feeder into that because, like, $10,000, like, how would they use it? Yeah. Would it go into travel, investing it or retirement?
Starting point is 00:08:31 Like, it's just, it's like a perfect bridge. Yeah, it's enough to do something. Yes. And I think, I mean, for me, it would be travel. If I just got $10,000, what would I do with it? Yeah. I think shopping. I mean, the answer is different for everyone, right?
Starting point is 00:08:51 You can also, I mean, if you're listening to this right now. That sounds bad, but she's going to shopping sporee, but that's, but the reason why she can do that is because she has all of her financial health in order in the other parts of her life where she does have like savings and retirement, you know, in order. But like you can split up. It's an order, guys. You can split up $10,000 in many ways. Like, right? Like you can do like $5,000. You can invest $5,000, you can spend $5,000, whatever.
Starting point is 00:09:17 But I know a little bit more about your finances. I think I would, I think I would buy myself. Well, now that we're, you know, now that we're brought. No. Oh, I don't know. I think I would buy myself a bulgarie bracelet. Is that $10,000? Oh, it's more.
Starting point is 00:09:33 Oh. It would subsidize part of the cost. It was subsidized part of the cost. Of your bulgarie bracelet. Yes, because, okay, I've been thinking about this, guys. It's the year of the snake. So I should get it this year, right? Okay, please weigh in on this.
Starting point is 00:09:50 Do we get matching ones? Just kidding. I don't know. That's too much. Like, I don't think I would wear that. I want to just go on an amazing scuba diving trip for like two weeks. Well, I'll be at home working, wearing my bracelet. Yes.
Starting point is 00:10:03 As you text me about your... As I'll be not working and scuba diving in, I don't know, the Maldives or something. Yeah. Actually, probably $10,000 wouldn't even cover that trip. No way. Yeah. I mean, maybe if you flew there on points or something. Oh, my God.
Starting point is 00:10:18 Yeah. But I would like to do something more experiential. This is how we're different. Like, you know we're sisters, but this is. is also where... No, I like experiential things too, guys. She likes experiencing the inside of a bulgari store with a sales associate. And some champagne.
Starting point is 00:10:33 Is it bulgari or bulgari? Bulgari. Oh. Bulgari. Bulgari. I guess when you get your bracelet, you can ask the sales associate how to pronounce it. Oh, we're still running. Okay.
Starting point is 00:10:47 Yeah. Okay. So back to the topic at hand. The one thing I'll add is that we kind of threw a lot at you in terms of answering the question, you don't have to do this all in one session. Like, this doesn't have to be a marathon four hour long discussion. That sounds miserable. I know it sounds mis. Just start with at least one question. Open the conversation, as we like to say. Open the conversation and also gauge their level of engagement. And I think also invite them to help drive, co-drive the conversation
Starting point is 00:11:16 with you and be like, this is something that we should revisit. Like, let's start the conversation now. let's revisit and talk about it multiple times, and that'll help us come to some sort of like operating agreement together. I know that doesn't sound sexy. I know that sounds so lame when it's applied to a relationship, but that is what you're building. Like, this is your most important relationship, and it is in many ways the beginning of your potential merging of finances. So you do need some sort of operating system. You need some sort of operating principles that you are both aligned with and that you can build on top of. Otherwise, if you have different assumptions going into living together and building a life together, that can sort of crumble pretty quickly.
Starting point is 00:12:03 Yeah. And I would say going into the conversation, lower your expectations if it's your first time having it. Like, don't make it a marathon. Don't make it four hours. And just use the first time you bring it up as a data collection session for yourself. Because like Jean said, it's like are they engaging with it? Like, are they open to talking? Are they, like, kind of secretive and kind of awkward? But then, like, you don't have to judge them for it, but, like, you have to understand why. Yeah. Are they defensive? Are they defensive about it? Or are they, like, not even answering the questions? So I think just using the first, you know, one or two sessions, like, you don't have to, like, be, like, show me your, like, bank account right now and, like, talk about savings right now.
Starting point is 00:12:43 Like, I wouldn't even do that if you guys haven't broached it before. But just using it as, like, for yourself, be very perceptive of like how they're answering the questions and their willingness to or unwillingness to engage. Like I think that is a really good indicator for yourself and like don't go into the session thinking you're going to like accomplish like 50 things and like 50 questions are going to be answered. But just like notice. I would say that's like a perfectly fine goal for the first like one or two sessions. Yeah. And you didn't ask about this specifically, but I'm kind of like reading between the lines of what you wrote in. I think a lot of times by having these conversations, you discover like one layer deeper, sort of the overall like living situation and like the way that your partner lives and approaches life
Starting point is 00:13:32 and kind of how they have been funding their lifestyle over the last, you know, X number of years because you mentioned he's a teacher, but you're still splitting all of your expenses when it comes to travel and like eating out and all that stuff. like maybe they are being subsidized by their parents or their family or that's actually really much more common than is brought up. So that's kind of like a question that you also want to better understand. Yeah. And then just to be a little bit more tactical to answer your question, let's say you collect all this information and the next step is moving in. I think that like when you're splitting rent, you don't have to do it proportionally like 50-50. Yeah. Like I think
Starting point is 00:14:14 very much like that is what we assume is the default but like this is your world you get to choose how you run your life with a partner and it doesn't have to be 50 50 honestly our recommendation is to do it proportionally so like whoever is making um you know like 70% of the income could then provide 70% of the rent split or 70% of like whatever expense split yeah that's what my one of my best girlfriends had has been doing with her boyfriend who became her fiance who is now her husband for a long time because he made a lot more than her and also he was the one that really wanted to sort of like upgrade their living situation so he was very much like driving that decision and so he was like you know what like I'm happy to pay more proportional to my income but that's
Starting point is 00:15:05 why it's also important to better understand the like sort of overarching financial situation of your partner. They may have other financial resources that are not just their sort of like everyday income that they see coming in every month. Yeah. So I would say the overarching tenor here is finding like what works for you and your partner like coming out of this conversation. I think on the opposite side, you like mentioned sometimes people are subsidized by their parents. On the other end of that spectrum, a lot of people still need to provide for their parents. Yeah. And that is something that they need to consider in this entire equation of what they bring to the table. And so it's a conversation. You're going in seeking to understand and learn more.
Starting point is 00:15:52 And I think going in with compassion and figuring out what works for you two as a pair is just the first place to start. Yeah. So hope this was helpful. Best of luck. Let us know how it goes. And congratulations. Yay. Okay. So the next. The next. question is about getting promoted over your work bestie. And we'll be right back after this break. I am a huge believer in science. As one of the top 25 women patent holders in the U.S., I live in the space where research, rigor, and innovation meet. So when I try something new, especially for health or skin, I want to know that the science checks out. That's why Sheree and I connected so deeply with one skin. The brand was founded by four women PhDs studying skin regeneration and stem cell
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Starting point is 00:17:27 After you purchase, they'll ask you where you heard about them and tell them that the Tiger sisters sent you. Try Onskine today. Your future self will thank you. And we're back. Okay, so the next question is someone who got promoted, yay, but they got promoted over their work bestie. Gene, can you please read the question? SOS Tiger Sisters, you're my heroes. Please save me from this work dilemma. I've been at a job for three years, and a few months ago, I got promoted over my work bestie. She's a year older and has been at the company a little longer, so it was a bit of a surprise to me. On the other hand, I'm much more ambitious, outgoing, and proactive at work.
Starting point is 00:18:03 She's much more reserved, and even though I've often encouraged her to advocate for her, herself, she mostly just assumes that hard work will be rewarded. She congratulated me when she heard, but I could tell she was a little shell-shocked about it. I'm not really her boss or anything, but I just got to sign the first project I'm running point on, and she's supposed to help me with it. So far, she's been pretty uncommunitive and resistant to doing things the way I would like. And given it's my first one, I don't want this to affect how my managerial work is being viewed. I feel like my options are either to stay up all night, redoing everything she does, if that's even possible or talk to my boss about what's going on, which I feel like could also be perceived as
Starting point is 00:18:40 me not succeeding as a manager, or try to talk to her directly, even though I feel like she'll take this poorly because she's very passive and hates confrontation. Please help. How can I smooth things over and get this project back on track at the next few weeks? Damn. This one is spicy. So I think this one is awkward. It's weird and it hurts because... Are you feeling awkward? I'm feeling kind of awkward because... I can imagine being in this person's shoes. And this is where like friendship and like the corporate environment kind of like butt heads and like work politics but also your friends with this person. It's just awkward. Friendship meets hierarchy. Yeah. It's so uncomfortable. So I think the first thing that you have to do is to address it head on and do not avoid it as a leader. Yeah. And I think like it doesn't have to be so direct and obvious. Like,
Starting point is 00:19:35 You don't have to go to your good friend and be like, hey, I know I got promoted, but you can still open the conversation with them and kind of make it more about the project and make it more about the task at hand as opposed to necessarily your relationship and make it, I think, focus the conversation back on your shared goal. So you are on a team together. you do have certain outcomes that you're trying to reach. So I think talk about the project. And then I think it also helps to not to like do a shit sandwich, but sort of like acknowledge. Acknowledge them as a team member and acknowledge their contributions and sort of like talk about how important they are to you both on the team and as a personal relationship. So I think that's how I would begin to approach it in having this conversation you mentioned. Yeah, I think when you recognize people for their contributions and what they bring to the team and the project,
Starting point is 00:20:42 like it can help with the thawing feeling of things being like awkward. And I don't think people expect that. Like it might catch them on their back heel in a good way. that like you're actually coming to the conversation with compassion rather than like, yes, you guys are working on this project together and perhaps this person is not helping out, but because you're coming in with much more compassion and wanting to collaborate more. And instead of saying like we're behind on this project, you're like, you're coming in much more collaborative. And I think another thing that's helpful that I have always done as a manager anyway, but in this instance, you could maybe ratchet it up a lot. little bit is to call out their contributions to your shared boss or to the like overarching boss in a positive way. Exactly. And like you don't have to only call out their contributions. Like you could make it like a team wide thing where you're, you know, if you've hit a certain milestone in the project, you can say like thank you to person Y for like driving this project. Thank you to person Z for
Starting point is 00:21:50 taking on this aspect of it. And thank you to my work bestie for doing this blah, blah, blah, blah, blah. so that they sort of like remember that it's a team effort and they feel recognized and they just get some sort of affirmation. Yeah. I think the affirmation is a great place to start. And if your project doesn't turn around after that and things are still slow moving and this person is not contributing the way they need to or like stepping up because of this awkwardness, I think that's kind of where you need to put your foot down. and stick to the facts of the situation and you have to bring it to your manager. Otherwise, like this person said in the question, like their managerial capabilities will be questioned.
Starting point is 00:22:37 Yes. And so I would take all the emotion out of it when you get to this point. Like stick to the facts of like, we have this project. It's due on this date. And work bestie is not contributing in XYZ way. And you're able to point to the facts. Yeah. Yeah.
Starting point is 00:22:55 You could even phrase it in a neutral way to your manager and be like, these are the blockers and then list that as like the primary blocker. And maybe there's another blocker that you can also call out. Yeah. But definitely do not just take on everything that your work bestie is not doing because that's kind of a formula for disaster. Yeah. It's going to stress you out, stress you out even more because you are taking on work. And it's not a long term sustainable path for you to increasingly take on more work. that this person should be doing.
Starting point is 00:23:27 Like for you as a manager, like this is also like kind of a great lesson, like your first great lesson in being a manager on how to handle uncomfortable conversations and how to make yourself a resource to that person and how to scale yourself when you can't be everywhere all at once. Yeah, I like that. This next one is really interesting.
Starting point is 00:23:50 So I'll read it out loud. So dear Tiger Sisters, my boss followed me on IG and keeps leaving comments like looks fun or where's the invite with my posts. It's starting to feel weird, but I don't want to seem uptight or offend them. Help. What should I do? This is really uncomfortable. Like I'm hearing this question and I'm getting like the chills on your behalf.
Starting point is 00:24:16 First of all, I think if you are a manager and this sounds familiar to you, like you need a clock whether or not it's appropriate or not, especially because you are the manager, you're leading a team. There's definitely like employee boundaries and the fact that like someone let you into their personal life, like allowing you or like, you know, accepting your request to like see their Instagram is a pretty big step. And like if you do overstep that as a manager, access revoked. I'm sorry. It's just like there's things that like people want to do outside of work. they're allowed to have a life outside of work and they can choose whether or not to share that with you, especially because there is a power dynamic and how you perceive them in the workplace might be affected by social media. Yeah.
Starting point is 00:25:04 I guess like speaking from my own experience, the way that I would handle it is that I would let the direct report or whoever was on my team sort of set the standard and like drive the level of social media engagement that they wanted. Right. Like they can make the first move. Like if they comment a lot in your stuff. Yeah. Then like you can take a hint or cue that like you are able to respond to their stuff. Yes. I mean, the reason I started like laughing to myself is because I've always worked at companies that kind of were social media.
Starting point is 00:25:38 So like since the very beginning when I worked at Farmville, I was like Facebook friends with my CTO, my like CFO, like every single person. We were always connected on social media. So I actually think I have like a pretty good. perspective here. So yeah, I think like take your cues from the person that you're managing, take your cues from the broader corporate culture. Yeah. But just don't overstep. Like, don't be the one to be commenting on everyone's like stories or posts when that's not the common. Yeah, when that's not the vibe. It's not the vibe. It can turn awkward really quickly. And there's not really that much upside as a manager for you to be engaging with your team or your employee that way.
Starting point is 00:26:21 if they haven't engaged with you that way first. So if you are an employee right now and your boss is doing this, like here are some, and you're uncomfortable with it, here are some things that you can do. I would say, mute them. Access revoked. Like they, if you don't want them to see your stories, they don't have to see your stories.
Starting point is 00:26:41 You are allowed to like soft block them in that way. You don't have to like completely remove them because then like, I don't know, that forces you kind of address it head on. It becomes a bigger thing. Like if it's just kind of. of innocent and you're just like, this is weird and I don't want them to know. Soft, block them and just make sure they don't see your stories. I think that's a perfectly fine thing to do.
Starting point is 00:27:02 Okay, the next question is, dear Tiger Sisters, my boyfriend Venmo requests me for everything. Okay, I'll read it. I'll read it. Dear Tiger Sisters, my boyfriend makes very good money, but still Venmo's me for half of every little thing, down to the meal. It's giving CFO not boyfriend. Should I say something? To me, okay, this is just my personal opinion.
Starting point is 00:27:28 That is a red flag. I can't take that in friendships, let alone in a relationship with someone that I am like, you know, potentially going to start a life with. If we are like counting pennies, nickels, dimes, quarters, like that is just not how I want to have a relationship with someone. But that's just my personal opinion. I know that a lot of people can make it work. So I guess let me say a more general statement. You can find the scenario that works for you. I think if you're in a relationship with someone who Venmo's every small thing and you are that way too, it can work really well.
Starting point is 00:28:04 Yes. Because you guys are speaking the same system. Yeah. Is that how I work? No. But let's just say that that's a very general system. It can work. And I think if you are with another person who has the same system of values when it comes to money and how you're splitting things,
Starting point is 00:28:19 like it can work if you guys are speaking the same language. I think the disconnect happens when exactly as this person says, it's like I'm not that type of person, but they're that type of person. And there's this like friction that definitely comes up. Yeah, I think this can actually even be expanded to just friend relationships because the way I've approached it is that for me typically, I prefer it to be just like a I treat you, you treat me situation. because I think that makes it more fun, even like in friendships.
Starting point is 00:28:52 So with my closest friends who are sort of also on the same page as me with this, like she'll treat me for one dinner. I'll treat her for another dinner. And like to me that just keeps it more, it just feels more fun that way. It feels more generous. Yeah, it feels more generous. It's like it just feels better to me. It makes more sense to me because that's sort of how I grew up.
Starting point is 00:29:11 And those are sort of, I think, aligned with my values. But I have some friends who are not like that at all. Like I do have some friends, not close friends. who have in the past like you know Venmo requested like sub ten dollars oh my god something yeah sorry i was about to go on and on a rant she was about to rant i was about to go on a rant i'm so sorry please continue your thought um and in those instances i'm like okay i guess that's fine like i can follow your lead there so like obviously if you're venmo requesting me for like eight dollars we're not gonna do this like we switch off on like treating each other to meals type of thing so like if i'm
Starting point is 00:29:48 make some sort of purchase on our behalf, then I'll also split it with you. Like, I can also request because that's clearly like the way that they operate. Yeah. So I guess I'm just like agreeing to you, agreeing with you and then also expanding it and saying that it also applies to friendships. But I do think that if this person is your boyfriend, that is a very substantive relationship in your life, to say the least. So you need to feel comfortable and be on the same page about how you.
Starting point is 00:30:18 you're going to operate. And it's definitely something to bring up. Oh, absolutely. Absolutely. Especially if like this is just like a little crumb of what it's going to be like if your life progresses to more than boyfriend. Yes. Of the apple pie of your life. Exactly. So you need to discuss it. So I was just triggered by what you said before. That's why I was about to jump in. I'm sorry. What are you going to say? Well, I've been in a friendship, like a very close friendship that was so frustrating for me. Because I am not a Venmo request person, like sub-10. Yeah. That's not who I am naturally.
Starting point is 00:30:57 Yeah. But someone who I was very close with in the past was like that. And you can't change them. You can't change them. No. People have baggage and like with how they grew up, how they think about money, how they like react to money in every part of their life. Like that's beyond.
Starting point is 00:31:13 Like I cannot change you. I've learned that. Yeah. Yeah. But like this person who I was very close with, Like Venmo requested me for like $2.80 of like a water bottle. And like this is someone who I considered like one of my besties. And when that happened, I was just like so like what?
Starting point is 00:31:29 I was like confused and like also hurt. And like I would never do that. She was hurt by the $2.80. Guys, $2.00 is the $0.80 can cut deep. It was so much more than that. Like I mean it was $2.80. But then this person did that for like multiple things. Yeah.
Starting point is 00:31:44 It started with a water bottle. Yeah. But then like. Well, and I'm sure part of it hurt. because, like, you had been coming at your relationship with your own standard, not transactionally. Like, I'm sure because since you're my sister, I presume you've, like, approached it similarly to me, even though we've never actually talked about this. But, you know, you probably treated this person to, like, many of random thing that you treat your friends to from time to time later. Like, I'll just cover this.
Starting point is 00:32:09 Yeah. And I just didn't feel that way back. So I was really hurt. It didn't feel reciprocated. Yeah. So that's where I felt really hurt. And I'm, and then I'm like, should I have? like Venmoed them for other stuff too, but then like I came back to my own values and I was just
Starting point is 00:32:22 like, that's just not who I am. Like, and that's who they are. Oh. So I was just like, I mean, the friendship didn't work out for other reasons, but this was like a mini red flag for me. Okay. Because of how they viewed relationships in their life anyways. Right. Yes. I do get what you mean. I actually do have friends, uh, or people that are like in my broader friend circle that my close friends have described them as like yeah I'm friends with this person but they are just very transactional like in in instances where I have been hurt or frustrated by the person my friend has described like yeah like you just have to understand they are a very transactional person and that is the bucket that I put them in so like that's hard for me to like reconcile with my
Starting point is 00:33:09 style of friendship and like back to your question if you are kind of more similar to me it may be hard for you to reconcile your way of like living with your new boyfriend. And I think it, it's not, it's not just about the money. It's like, it never is. It's more so about your approach to life and maybe your general, like where you fall on the spectrum of transactional to just kind of more, I don't, I want, I guess the word is generous, but then it makes it seem like generous is contrasted as the opposite of transactional, which is not always true, but until I think of a better, more neutral word, it is the spectrum
Starting point is 00:33:56 of like transactional to generous. So like, I think for one of the most important relationships in your life, you need to be pretty close to each other. Like you can only be, with how you see your values. You need to be within the same standard of deviation within that spectrum or maybe only one standard deviation apart. Yeah. Not you bringing statistics into this. She said standard deviation. You know what I mean?
Starting point is 00:34:21 Yeah. Like you can't be on opposite ends of the first spectrum, especially with someone who might turn into your long-term partner. Yes, because then it's going to be the same thing is going to be applied not to like extrapolate too much, but I will. And it's not just going to be. She will. I will.
Starting point is 00:34:36 It's not just going to be about Venmo requests. It's going to be about chores. It's going to be about who has. as what responsibilities. Like, it's going to be, you know, this. Child care. Child care. Like, clearly your boyfriend is very, um, tiki tacky.
Starting point is 00:34:52 I don't know. Like, tiki tacky, like little, like, um, counts. They're keeping count. They're keeping count, literally. They're keeping count. They're keeping count. They have a receipt. Enter cricket sounds.
Starting point is 00:35:06 Um, yeah. I would say also, I think I might be coming off kind of intense. I realize that. But that's also how. approach relationships and friendships with like if I invite you into my close inner circle like I feel really hurt when like trust is broken or like some sort of you know agreement between how we look at relationships is broken I think I can have acquaintances in my life who are Venmo kings and queens like sure we can we can settle that five dollars and fifty cents on Venmo like I can have an
Starting point is 00:35:39 acquaintance like that but if you are in my inner circle we such as like a boy, friend or like a bestie. Yeah. We better be within the same standard deviation of values. This episode not brought to you by Venmo. And that's it for this week's Tiger Sisters advice. So when you're talking about money, power, and love, remember, it can be broken down into strategy and frameworks.
Starting point is 00:36:06 We hope this was helpful. Please continue to send in your questions. And remember, it's not about being perfect. It's about having these frameworks that you can apply to all different parts. of your life so that you can sort of go through life more easily. Yeah. And I would also say it's trial and error. Like things are never perfect on the first time. But as you keep at it, you have these hard conversations. It gets easier and easier. You build self-confidence along the way in yourself. And like things get better as you keep
Starting point is 00:36:35 trying them. Yeah. Also, we really want to hear from you guys just to emphasize that. So please write in, leave comments. We want to know if and when you agree with us and also if you disagree with us. Like, let us have it. I'm very curious. Yeah, we want to hear your guys' thoughts. Thank you guys so much for tuning in to this episode of Tiger Sisters. We'll see you next time. Bye.

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