Episode 34. It’s unromantic if my boyfriend doesn’t pay for date night

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Ashley: [00:00:03] I feel like my spending is genuine, but I feel like he doesn’t think that it is.

Josh: [00:00:08] You do it to kind of check it off out of the box every now and then, and it’s not like a genuine we’re in this together situation. I’m not going to be able to provide the life that she expects.

Ramit Sethi: [00:00:21] Which makes you feel what?

Josh: [00:00:23] Like not good enough, scared that that’s where her mind goes first, is the cost of things.

Ramit Sethi: [00:00:30] Would you say that the things she brought up to you are shallow?

Josh: [00:00:34] Somewhat, yes. I hate that this is the subject matter, like just I hear a lot about money, like how big is the ring? Where is the wedding? These nanny things. Like those aren’t what’s going to get us through in the long run, things can happen.

Ramit Sethi: [00:00:49] If you had to bring up who’s going to pay for the meal ahead of time, Ashley, how would that make you feel? 

Ashley: [00:00:58] Annoyed.

Ramit Sethi: [00:00:58] Mm-hmm. Why is that?

Ashley: [00:01:00] Because I want him to pay for it, because he’s my boyfriend and I feel like that is the gender role. Now that I’ve been in my job for the last five months making good money, I feel like I’ve contributed more, but there is still somewhat of that expectation of him picking up the check more than me. I just feel like on date night, it’s more romantic when the guy does it.

Ramit Sethi: [00:01:29] What do you expect when it comes to money? Do you expect your partner to take the lead on paying for things? Do you expect for them to buy you gifts? Do you expect for you both to chip in 50-50 for joint expenses? All of us have expectations around money, but very few of us actually interrogate our own beliefs. We almost never talk about our expectations candidly. We almost never sit down and share what we expect, because most of the time, we don’t even realize what we actually want. In today’s conversation, you’re going to hear what happens when two partners have very different expectations of money. 

Meet Ashley and Josh, who recently started dating, and they’ve started to talk about moving in together, and getting married, and even having children, but they have an issue that they described to me as 10 out of 10. Ashley thinks that Josh should pay for everything when they go out for date nights. As I speak to them, I start to peel the layers back of their expectations, and at one point, I was hearing Ashley dance around what she really wants, and I encouraged her to just say it out loud, she was almost physically unable to ask for what she wanted. 

You’re going to hear more about this in today’s episode. And as a little bit of background, Josh didn’t mind paying for Ashley when she was unemployed, but he thought it would be temporary. So, after she got a job, he was surprised that she still expected him to pay for certain things. Now, Ashley earns $140,000 a year. That’s 70K base, and she’s on track to earn 70K of commissions, maybe more. She has $18,000 of debt. Josh earns $160,000 and he has $70,000 of debt. 

Now, you may remember this dynamic with an earlier couple on the podcast, Pablo and Monique. That was Episode 17, called I Think He Should Pay for Everything, Because He’s the Man. This might seem like the same situation, but there are crucial differences, including the fact that Josh and Ashley are both in their mid-30s with similar incomes. Let’s listen in to Ashley and Josh on I Will Teach You To Be Rich.

Ashley: [00:03:58] I feel like there’s always some sort of fight heightened around it based off of money and who’s expected to pay. He feels like I expect him to pay for dinner, so I wouldn’t say it’s like a one-off situation, but last time, we went out to dinner with them, I knew that he had some anxiety around paying, I don’t think we’ve ever gotten out for dinner with them, and the bill’s been under like 200 or 250 a couple, I ended up picking up that check, so there wasn’t a fight around the last time, but any prior dining experience we’ve had with them, he’s quick to say no, because he assumes that he will be picking up the check.

Ramit Sethi: [00:04:39] And out of the last 10 times you’ve gone out with them, how many times has he picked up the check?

Ashley: [00:04:44] Every time, except for the last time.

Ramit Sethi: [00:04:47] So, why are you only mentioning the last time in that example?

Ashley: [00:04:50] Well, you said the last time.

Ramit Sethi: [00:04:51] Okay. So, nine out of 10 times, he’s picked up the check. The check tends to be at least a couple of hundred bucks for the two of you, at least. So, what happens when you propose, “Hey, we want to go out with this couple next weekend, what do you think?”, what is that conversation like?

Ashley: [00:05:08] I feel like it is me making sort of like excuses of why we’re going out with them, like, we haven’t seen them in a long time, you really like them, just trying to like create some sort of like friendly environment around it, so he’s not immediately thinking, “Oh, well, I have to pay for it?” He does really like this couple very much, it’s just we do have this history of only going to restaurants that cost a lot of money, and Josh, he really values spending money on experiences, where I do as well, but I also love wining and dining.

Ramit Sethi: [00:05:44] Notice the pattern. She’s asking, he’s deciding. It’s a common dynamic. Personally, it’s one that I hate. And you see it a lot in straight couples, it’s almost always the woman asking, making the case, trying to convince her partner, and then the man sitting back, crossing his arms, and coming up with reasons to shoot it down. I hate this dynamic because it’s invisible to the participants, they don’t even realize that it’s a dynamic. 

And if you ask them why, they’ll often be visibly startled. If I push, they’ll often admit that, “Well, that’s how their parents did it”. I also hate it because they don’t realize there are other ways. When I ask them, do you want to go the rest of your life with one of you trying to make the case for something and the other coming up with reasons to say no, they’ll both readily admit, no, they don’t want that. 

What they’re missing here is having a common goal. You really should not be fighting over the price of asparagus, or at a certain point, going out to dinner. These are three-dollar questions or 100-dollar questions. And ultimately, I want you to be thinking much bigger than this. So, I just want to point this dynamic out to you, because it’s really common and it’s often invisible to the people in it, but it can be very, very destructive.

Ashley: [00:07:05] In the beginning of our relationship, I wasn’t working for the first time in a long time in my life, so he was really paying for a lot of things during that part of our relationship. And once I started working at my current job, I do have some expectation of him paying for dinners on date night like that.

Ramit Sethi: [00:07:23] What kind of expectations?

Ashley: [00:07:25] Just because he’s the man and he’s the boyfriend, and I just come from that kind of world and environment, where especially on date night, I just feel like it’s important for the guy to pick up the check. I think he actually does have a pretty good idea of what I want, and that’s really come to light I feel like this last week, and we’ve had some pretty tough conversations about it.

Ramit Sethi: [00:07:49] Like what? What happened?

Ashley: [00:07:51] Josh, are you okay with me sharing or?

Josh: [00:07:55] Yeah. Say the right thing, yeah, definitely.

Ashley: [00:08:01] Specifically last night, we had a conversation just around us moving in together, and kind of just expectations about what the future looks like, and getting engaged, and married, and kids. And I definitely have had a notion in my head, doesn’t mean I’m not willing to try something new or change it, but it definitely led to a really tough conversation, and me crying, and just being really upset, and I could tell he was obviously, visibly upset, but it all ties back to money.

Ramit Sethi: [00:08:42] Okay. I want to ask you a couple of questions about these expectations. A lot of times, often with gender roles, especially, everyone’s got these hidden expectations, nobody wants to come out and say it, because it makes it unromantic, and so people go 50 years resentful of their partner. All could be solved with a single conversation. So, you mentioned he’s the guy, he’s the boyfriend, finish that sentence, he should pay, because what?

Ashley: [00:09:12] Because he’s my boyfriend and I feel like that is the gender role. Now that I’ve been in my job for the last five months making good money, I feel like I’ve contributed more, but there is still somewhat of that expectation of him picking up the check more than me, but I just feel like on date night, it’s more romantic when the guy does it.

Ramit Sethi: [00:09:38] Okay. And if he pays for you, that means what?

Ashley: [00:09:47] I don’t know, because I know that he loves me, I know it has nothing to do with love or anything like that, it just is something I’m used to.

Ramit Sethi: [00:09:57] Mm-hmm. Does it make you feel a certain way if he pays for you?

Ashley: [00:10:01] I mean, makes me feel good. It makes me feel, I guess, yeah, loved.

Ramit Sethi: [00:10:05] Mm-hmm. Isn’t that interesting? At first, you said, “It’s not about love. I know he already loves me.”, and yet 10 seconds later, “When he pays for me, it makes me feel loved”.

Ashley: [00:10:14] Yeah.

Ramit Sethi: [00:10:15] Are there any other words you would use to describe how it makes you feel when he pays for you?

Ashley: [00:10:20] Special.

Ramit Sethi: [00:10:21] Mm-hmm. What does that mean?

Ashley: [00:10:23] That I’m the girl in his life, and he wants to show that I’m special and that he loves me by taking me out on date night. And it doesn’t have to be a 200-dollar dinner. Date night could be $75, it’s date night.

Ramit Sethi: [00:10:40] What if he doesn’t pay for you? What does that mean?

Ashley: [00:10:46] Normally, I feel like we’ve talked—well, we haven’t had the situation on “date night” where he hasn’t paid, but like last weekend, we went out just for like an easy Friday night dinner, I ended up picking up the check. Again, I did not tell him ahead of time, I just did it when we got there. I know that he would like me to tell him ahead of time, so he’s not, I don’t want to say stressed about it, but he’s not just automatically assuming that he’s going to be picking up the check.

Ramit Sethi: [00:11:20] And how about if it were at the dinner with this couple or any other friends, and the bill comes in, he just casually lets it sit for a while, and eventually, you pick it up and pay for it, how would that make you feel?

Ashley: [00:11:33] I would probably be pretty upset afterwards, in terms of like, not because I had to pay for it, because you just like left it sitting there and I just wouldn’t want to be embarrassed in front of our couple friends.

Ramit Sethi: [00:11:45] Okay. Let’s play that out one more time. The bill comes and he pushes it towards you.

Ashley: [00:11:50] I think that’s rude.

Ramit Sethi: [00:11:51] Okay. So, basically, no matter what, you’re not going to feel good if he’s not paying, is that correct?

Ashley: [00:11:57] Yes and no. Like yes, I do want him to pay, but I wouldn’t be upset paying in the end, but I would be upset with him either pushing the bill towards me or letting it sit just more out of like embarrassment and not having had this conversation beforehand.

Ramit Sethi: [00:12:14] Great. Okay. Thank you. 

I was gently pushing her to answer the question, because I want to understand her beliefs about why she thinks Josh should pay. And from her answers, I have to tell you, I’m a little confused. She claims that she wouldn’t be mad if she paid, but when I probed her, there’s not a lot of consistency in her answers. I will say that I actually admire how honest she is about her beliefs. 

When it comes to gender roles, they are some of the most subtle, invisible scripts that exist. There are tons of unwritten expectations when it comes to dating, and relationships, and gender, but very few of us are willing to say them out loud, to articulate them explicitly. Ashley is, so I appreciate that. But when I tried to push her further to understand why she believes those things, that was a different story.

Josh: [00:13:16] I feel like things should start off in more 50-50 for this type of stuff, and then we go from there together.

Ramit Sethi: [00:13:23] And 50-50 to you, what does that mean, exactly?

Josh: [00:13:25] I’ve mentioned that if somebody’s budget is outside of what the other one’s comfortable with or suggest something that the other one isn’t necessarily like part of their normal deal, we should start at a more reasonable level, then if we’re comfortable elevating that, we should. So, if we want to go to a 300-dollar dinner, like, hey, do you want to spend that right now? Yes, cool. Let’s go. No. Is it not a good idea? Should we split it? But it should be talked about a little bit ahead of time, because, again, it kind of sours it, and as you mentioned, the expectation is that I’m going to pay for these every time.

Ashley: [00:14:01] Even though I might be going into a dinner with or without this couple thinking about paying for dinner, I’m just not as communicative about saying that, don’t worry, I know we’re going out to dinner tonight, like I’ve got this.

Ramit Sethi: [00:14:16] Okay. Why do you think that is?

Ashley: [00:14:18] Sometimes, this is going to sound so weird, but it’s like I like want him to read my mind, but I know that he can’t. 

Ramit Sethi: [00:14:25] Mm-hmm. If you had to bring up who’s going to pay for the meal ahead of time, Ashley, how would that make you feel?

Ashley: [00:14:39] Annoyed. 

Ramit Sethi: [00:14:39] Mm-hmm. Why is that?

Ashley: [00:14:42] Because I want him to pay for it.

Ramit Sethi: [00:14:47] Okay. We just cut right to the end of it. Okay. So, ultimately, you want him to pay for it. Okay. Fine. You’re being very open with what you want and what you expect. And so, you’re telling me that if you had to proactively start a conversation, where you’re going to have to go out of your way, and say, “Hey, Josh, even though I want you to pay, I will have this uncomfortable conversation and I will pay”, that would be annoying to you.

Ashley: [00:15:16] Yes. And it would also be annoying to me if we said, “Okay. We’re going to dinner Friday night with this couple”, and if then he said to me, “Well, like I really want you to pay for this”, like I would be annoyed. 

Ramit Sethi: [00:15:30] Because?

Ashley: [00:15:30] Would I say no to dinner because of it? No. But just because like it’s date night, I want him to pay.

Ramit Sethi: [00:15:38] Date night equals he should pay. Is that right?

Ashley: [00:15:43] Most of the time, yes.

Ramit Sethi: [00:15:44] Is that 100%?

Ashley: [00:15:46] No. Because like I think we have casual date nights where I’m more than happy to like pick up the check, like the nicer date nights.

Ramit Sethi: [00:15:53] Okay. And why is that?

Ashley: [00:15:54] Just because I feel like that’s what should be done.

Ramit Sethi: [00:15:57] Uh-huh. Keep going.

Ashley: [00:15:58] It’s like it’s what I’ve had in the past. It’s what I’ve grown up with. It’s what I’m used to. Back to that what I expect situation.

Ramit Sethi: [00:16:09] Yeah. 

Okay. I think I reached the end of what I can get from Ashley about her attitudes towards paying for dates. That last sentence really says it all, “It’s what I had in the past and it’s what I’ve grown up with”. So many of our money beliefs, especially ones in areas like dating and relationships, boil down to, I expect X, because that’s what I had and that’s what I’ve grown up with. That can make perfect sense for the person saying it, but it can be very frustrating for the other partner in a relationship. I’m wondering, are you curious when this first started happening?

Josh: [00:16:50] When we first got together, I knew that she was very capable, smart, attracted to a lot of great things, about Ashley, and she didn’t have a job at the time. But I know she had a job before, it was during the pandemic, so didn’t typically judge that situation. So, really, these dinners are kind of a buildup of more of a history of things feeling a little out of balance. 

And I’m okay with some of the more traditional gender roles in certain ways, but I feel like it starts with balance, then you kind of see where things fall there. And I don’t feel like we’ve really re-centered since she’s been working again, because I’ve picked up a lot of slack. We’ve maintained a pretty fun life last year beyond dinners that was generally the same budgetary situation.

Ashley: [00:17:47] So, I feel like my spending is genuine, but I feel like he doesn’t think that it is.

Ramit Sethi: [00:17:52] Well, ask him, Is that true? Ask him.

Ashley: [00:17:56] Josh, do you think that’s true, that it doesn’t feel genuine?

Josh: [00:17:59] Somewhat. Mm-hmm. That it’s a little bit pick and choose, you do it, I feel like, to kind of check it off out of the box every now and then, and it’s not like a genuine we’re in this together situation.

Ramit Sethi: [00:18:16] So, I heard both of you explain that you want to be part of a team, which is great. You’re both on the same page there. And I heard that both of you would like to have better conversations, preferably ahead of time. That’s awesome. But now, I just want to cut to the chase. So, in your ideal world, Josh, you have this conversation about this dinner, so what’s the decision you’re both going to make? Who is paying?

Josh: [00:18:42] I think it’s just based on what the communication is at that time. For example, if someone’s recently received a bonus, or if they’ve made a payment towards some debt that we’re trying to do, or it should just be towards our shared goals together at this point in the relationship, like-

Ramit Sethi: [00:19:00] Can I tell you something?

Josh: [00:19:01] Yeah.

Ramit Sethi: [00:19:02] You want to have this conversation every time you’re planning to go out to dinner?

Josh: [00:19:05] No.

Ramit Sethi: [00:19:06] It sucks. Look at her face. Look at her face. What is she doing right now?

Ashley: [00:19:09] So unromantic.

Josh: [00:19:11] I don’t want to have this conversation every time we go out to dinner.

Ramit Sethi: [00:19:14] Okay. She just said something really important. What did she just say and what do you want to do about what she just said?

Josh: [00:19:22] I didn’t hear her. 

Ramit Sethi: [00:19:23] She said, “So unromantic”. That’s like a huge red flag. When she says those two words, “So unromantic”, you know what my first instinct is if I’m in your chair right now? I go, oh, that’s interesting, tell me more, what do you mean by that? Do you know, Josh, what she means by those two words, “So unromantic”?

Josh: [00:19:52] I’d love her to explain. That way, I don’t assume.

Ramit Sethi: [00:19:54] Please.

Ashley: [00:19:56] I think especially as women, we all want some sort of fairy tale of some sort. I’m not looking for the cupcake wedding dress in the castle on top of the hill by any means like that, but in terms of romance, like I still want romance. I still want to be swept off my feet by him. And he does do so many thoughtful gestures, I mean, probably one of the most thoughtful gift-givers I’ve ever met in my life. I’m really referring to more of like typical date night, get dressed up, go to a nice dinner. I just want to go have some good food, some wine, come home, be romantic with each other, and not think about the check, or the bill, or who’s paying, or the conversation we had, and if it turns into a fight, because that’s where it becomes unromantic.

Ramit Sethi: [00:20:50] Okay. What does romantic mean to you when it comes to these dinners?

Ashley: [00:20:55] Just unplugging, being just the two of us together, and reconnecting after the week, and just being romantic and loving with each other, and enjoying some good food and wine with our company. 

Josh: [00:21:05] I want them to be fun, and feel natural, and applicable to our life at the moment.

Ramit Sethi: [00:21:12] Meaning what?

Josh: [00:21:14] Meaning that that’s within our like means and budget, but it’s because, again, she’d mentioned that, nine out of 10 times, this wouldn’t be a subject if there is a little bit more give and take, this wouldn’t be a specific subject.

Ramit Sethi: [00:21:29] I get it. And what would that number be that this would not be a subject? Right now, it’s 90-10. What would it be in your mind?

Josh: [00:21:37] 60-40, 70-30, somewhere where it’s almost like it’s not a surprise, like I’m falling out of my chair.

Ramit Sethi: [00:21:44] Okay. You know what’s interesting? The two of you, first of all, I love that you both want to communicate more. Yes, that’s awesome. I’m going to show you how to do that. I’ll tell you just point blank, it’s super unrealistic to expect to go through this financial investigation before every dinner. It’s just not going to happen. And that’s okay. I don’t think you both need to do that or want to do that, but what I’m hearing, actually, is you’re naturally starting to develop these rules of thumb, but I don’t think you’ve actually realized it. 

College athlete is going to wake up at 6:00, because they need to go eat early before everybody else, et cetera. With money and relationships, you’re going to develop rules of thumb. Here’s what I just heard. Ashley says, “Hey, I will happily pay for these types of dinners, but I would like you to pay for those types of dinners”. Wow, that’s a rule of thumb. Now, I’m not saying it’s right or wrong, and you two can certainly discuss it and negotiate over that, but that’s a really interesting rule of thumb. 

Josh has mentioned, “It should be within our means”. Okay. Those are just words. I would like to be a little bit more specific about that. What does that mean? Are we only spending X dollars or are we never ordering wine? You can discuss and negotiate that, but that’s a rule of thumb. And you come up with two or three rules of thumb around these dinners, you never have to have these financial investigations ever. Do you see what I mean?

Ashley: [00:23:14] I think having what you were just saying like an agreement of, I’ll cover these types of dinners if we go on a date night, maybe you say based on what we can do to get out of our debt and all of that, based off of what’s in our budget, how many date nights can we go on in a month or every couple of months, he pays, and then there is, obviously, like we shouldn’t spend over X amount.

Ramit Sethi: [00:23:44] Can we just come up with these rules right now? I feel like we’re all talking around them. Can we just do it? I mean, I’m here.

Ashley: [00:23:49] Okay. If it’s a dress up weekend dinner, where we have a nice dinner and nice wine or cocktails.

Ramit Sethi: [00:23:59] Finish the sentence.

Ashley: [00:24:01] You want me to give an amount, don’t you?

Ramit Sethi: [00:24:03] No, I want you to give me a complete sentence. You don’t even know, but you are finding it impossible to say one part of this sentence. Give me a complete sentence.

Ashley: [00:24:13] I want Josh to pay for the date night dinners, the weekend dress up date night dinners.

Ramit Sethi: [00:24:24] You look like you’re physically in pain. I’m enjoying watching this. Josh, is this not fascinating?

Ashley: [00:24:33] Because he’s going to like hate me for this. 

Josh: [00:24:35] This is great.

Ramit Sethi: [00:24:36] So, Josh, I know why I’m enjoying this, okay, I have a very dark sense of humor, but, Josh, why are you enjoying this?

Josh: [00:24:44] Because it’s good to explore these things and get them out, because we say that we communicate well, but we talk a lot.

Ramit Sethi: [00:24:50] Yeah, you guys talk so much. You use a lot of words to dance around specificity.

Ashley: [00:24:56] I’m super uncomfortable.

Ramit Sethi: [00:24:59] Why?

Ashley: [00:25:00] Because I have to pinpoint exactly what I’m looking for, and I don’t, A, want to upset Josh, and B, I’m definitely a little scared to fully ask what I want.

Ramit Sethi: [00:25:16] Why is that?

Ashley: [00:25:16] Because I don’t want it to like ruin or affect our relationship. It’s so funny because like in my normal daily life, my work life, I’m very straightforward, I ask for what I want, I get what I want, I’m very convincing, should have been a lawyer, but when it comes to personal life, it’s scarier, for sure, because I don’t want to either say the wrong thing, whether or not it’s something that I want, I’m still scared to say the wrong thing, to not upset the other person.

Ramit Sethi: [00:25:49] And if you say the wrong thing and you upset your partner, what happens? Finish that sentence for me.

Ashley: [00:25:59] I’m scared of him thinking that we don’t belong together, which is, yeah.

Ramit Sethi: [00:26:06] And then? 

Ashley: [00:26:08] And then, we’re not together, and then we break up because of it.

Ramit Sethi: [00:26:11] Yeah. So, deep down, this concept is that if I say what I really want, then he might leave me.

Ashley: [00:26:22] Yeah.

Ramit Sethi: [00:26:24] Ashley is scared to ask for what she wants. She can barely even utter the words. This is a terrible way to live. It’s how we minimize our dreams and shrink our desires until they’re snuffed out like a dying candle. I see this pattern in all kinds of people, but it tends to be much more common with women. I’ve always said that I consider it a tragedy to live a smaller life than you have to, and here, you can see how subtle this is. If you can’t even utter the words of what you want, how can you ever expect to live that life? 

I would much rather that, Ashley, be open about what she wants, confident enough to have a discussion with Josh, instead of hiding and hinting. It’s not fair to him and it’s not fair to her. Right now, she’s playing this part of her life on defense. Now, the common reaction for people is to say, “Just ask for what you want”, but that never works. There are layers and layers here, and I want to understand what’s underneath her beliefs about money. 

What do you do instead?

Ashley: [00:27:41] I mean, yeah, either hide what I want or I dance around the subject.

Ramit Sethi: [00:27:47] She admits it. This is a huge moment of realization for Ashley, and I love that she didn’t push back. Pushing back, denying it, that’s the natural tendency of someone in her situation who just realized something profound. That makes all of us uncomfortable, so naturally, we tend to lash out or deny it. But not Ashley. She’s listening. She’s really taking it in. This is a very positive sign for our work together. I asked her to tell me more about her expectations for life. Now that she’s had a breakthrough and she’s being more transparent about what she expects from Josh, what else does she envision for her life?

Ashley: [00:28:31] I’m hoping that my parents will pick up most of the tab for the wedding. How much? I don’t know. What are we going to have to contribute? Talking about just starting to save for a family. Like last night, he said, “Well, we’ll just like wing it. We’re not saving.” And I’m like, well, that gives me anxiety. Like you can’t just like wing it. You can’t wing it when you have a baby. 

Like you have to start putting aside money for when you want to get pregnant and have a child for the future. And that definitely kind of scared me a little bit and gave me a little bit of anxiety. Last week, I was saying about having a nanny for like a little bit to help out with the baby at first, and then he was saying that like, I live in this like rich world, where that’s not normal, and who’s going to be paying 50, 60K a year for this nanny?

Ramit Sethi: [00:29:21] Okay. And what is your thought about that?

Ashley: [00:29:23] This is where it gets hard, is because I grew up, I had a nanny, I had a housekeeper, those were all things that were normal to me.

Ramit Sethi: [00:29:34] So, it sounds like you have a vision for the kind of life that you want. You were pretty open with Josh about your vision and what you expect.

Ashley: [00:29:47] Yeah.

Ramit Sethi: [00:29:47] I want to compliment you on that. That’s impressive. Okay. Now, Josh, what was your general tenor as you were hearing this? Like what would you describe your body language as?

Josh: [00:30:01] I hate that this is the subject matter, like just I hear a lot about money. Like how big is the ring? Where is the wedding? These nanny things. Like those aren’t what’s going to get us through in the long run, things can happen, medical things can happen, crazy things can happen, where the money is going to be a challenge. What about like, are we great partners? Do you trust me to take care of a child? 

Like through thick and thin, would we survive together regardless of what the outcomes were? Those are kind of what I was hoping to hear more of, versus how much rings cost and things like that, because it kind of kills the vibe for me. Like we’ve been together for a year, we’d love to propose as soon as the opportunity presents itself, but when I hear about the ring cost and I picture it, like it kills the vibe.

Ramit Sethi: [00:30:53] It’s interesting, Josh, you say that it kills the vibe, it reminds me very much of when Ashley said that it’s not romantic to talk about who’s going to pay for dinner. Do you both see that you feel the same way, but you just use different language to describe it?

Ashley: [00:31:13] I already got there before you even said it. I made that connection as soon as he said it.

Ramit Sethi: [00:31:17] Yeah. And so, Ashley, when you feel unromantic about these pre-dinner conversations, how does that make you feel?

Ashley: [00:31:26] I don’t know.

Ramit Sethi: [00:31:27] Try to articulate it.

Ashley: [00:31:29] Yeah.

Ramit Sethi: [00:31:31] Say it out loud. It helps you often find the emotion. When I think of Josh opening up Microsoft Excel to look at our numbers before we go to dinner, it makes me feel what?

Ashley: [00:31:43] It makes me feel like we’re already dampening the mood of the evening. It makes me feel it’s like just so rigid and unromantic. I mean, yeah.

Ramit Sethi: [00:31:57] Okay. Good. Now, Josh, finish this sentence for me. When Ashley talks about our long-term prospects, but the topics she brings up are the size of the wedding ring, where the wedding is going to be, and how we need to have a nanny, it makes me feel what?

Josh: [00:32:17] Like I’m not going to be able to provide the life that she expects.

Ramit Sethi: [00:32:23] Which makes you feel what?

Josh: [00:32:25] Like not good enough.

Ramit Sethi: [00:32:31] Anything else?

Josh: [00:32:32] And like a little scared that that’s where her mind goes first, is the cost of things. 

Ramit Sethi: [00:32:39] Because? 

Josh: [00:32:40] I value the deeper connection that I think that we have beyond that and it kind of, yeah, just feels not good enough, frankly.

Ramit Sethi: [00:32:53] It’s interesting you use the word deeper, that deeper connection, would you say that the things she brought up to you are shallow?

Josh: [00:33:02] Somewhat, yes.

Ramit Sethi: [00:33:03] Yeah, I detected a resentment from you and it was interesting that you took it all on yourself. When I just asked you, how does it make you feel, you said, “It makes me feel like not enough, that I can’t provide”, but I also detected this latent sense of resentment that she would even bring these things up, because they seem so shallow. Listening to what both of you just did right there, are there any insights that you take away from that, Ashley?

Ashley: [00:33:35] Yeah. I mean, to talk about this last night and to hear it again when I don’t feel as like emotional about it, obviously, it hurts and it makes me feel awful, because at the end of the day, like I love him so, so much, like I want to be with him, and I don’t want him to feel like he’s not good enough or that I don’t want him to resent me, and I don’t want to resent him either. It definitely goes both ways. 

And I think we’re kind of stuck between that rock and a hard place of having expectations and wanting to be together, but I think for us, the biggest thing is, how can we tackle the debt that we have, get that out of the way, so we can then focus on building a financially stable life together, and hopefully get to the same end goals that we have about expectations that we do have?

Ramit Sethi: [00:34:32] Love that. I love the way you put that. Okay. Great. 

The thing I love about Ashley and Josh is that they’re willing to be real. Ashley is telling us what she expects and Josh is also telling us how he feels about Ashley’s expectations. Interestingly, both of them tend to soften what they really believe. You heard that Ashley had trouble even saying the words and Josh initially blames himself, so I have to probe in order for them to share what they actually believe deep down. 

Now, think about that. If I have to ask this many questions to get to the real truth, do you think that they even know what each other believes? Do you think they even know what they, themselves, believe? I think their beliefs go a lot deeper than the spreadsheet, and we’re starting to discover that, but they believe that their debt is the main thing stopping them from their rich life.

Ramit Sethi: [00:35:37] How would you both describe your incomes? Josh, you make $160,000 a year. Ashley, you make $140,000 per year. How do you feel about that? Josh?

Josh: [00:35:53] It feels like less than it should.

Ashley: [00:35:55] I agree. Like it feels like $3 at this point with this economy and where we live.

Ramit Sethi: [00:36:03] So, all bad stuff, you guys don’t want to compliment yourselves at all for making a lot of money?

Josh: [00:36:09] I think 160,000 should be able to make more things happen, potentially, than I am, and would expect it to be a little more comfortable in certain situations with that income level than I actually am.

Ramit Sethi: [00:36:23] Why do you guys seem so miserable about your income? Who’s that guy on Winnie the Pooh, Eeyore?

Josh: [00:36:28] Yeah.

Ramit Sethi: [00:36:28] He’s always depressed. Oh, how do you guys feel about making 160 and 140? Oh, it sucks. Yeah, I mean, it feels like $3.

Josh: [00:36:37] It’s what kind of hurts about it is I know that it’s a good income, but because of the debt, the payments that I’m making and potentially some spending habits, it doesn’t feel like I’m enjoying the benefits of achieving that level of income.

Ashley: [00:36:51] And I don’t think that my income is crap by any means. I think also coming off of a hard time during COVID, where I didn’t have a job for a while, finally having that income again, it feels great, but like there is that debt cloud looming over me.

Ramit Sethi: [00:37:10] Let me just give you one piece of directive feedback, Ashley. The fact is you make $140,000 now. That’s really interesting, by the way, the way you described it in your document to me. Let me read it off verbatim, because it tells you everything you need to know. It says, “Ashley, 140K per year, 70K base, plus 70K commission”. That’s clue number one. And then, clue number two, it says, “/I have only been at this job for five months, so I have yet to see my full commission and earning potential”. What are those two clues telling you, Ashley? Why did you describe your income with all these caveats?

Ashley: [00:37:55] Because that 140 is my projected income without having been at this job for a full year to see if I’m going to make my quarterly commissions, I won’t know exactly what my annual salary is going to be.

Ramit Sethi: [00:38:12] I totally respect that. I know how sales goes. How confident are you that you will make 140?

Ashley: [00:38:18] At this rate, very. I’m doing very well at work.

Ramit Sethi: [00:38:21] So, can we just call it 140?

Ashley: [00:38:24] Sure.

Ramit Sethi: [00:38:24] Can we stop discounting it and creating all these scarcity-based caveats that really give you an out from being specific about what you make and how much you can afford to spend? 

Ashley: [00:38:38] Yes.

Ramit Sethi: [00:38:39] Yeah. What you did is classic scarcity. I see it so often. And I’m going to share what I see, because I think it will be very illustrative to you, people who grew up lower middle class, people who didn’t have any money, people who were laid off or unemployed for a while, all these groups, when they suddenly start to make a considerable amount of money, they refuse to believe it. 

They see the number on paper, I go, oh, my God, you make 70K, or 100K, in your case, 140K, and you know what their first answer is? “Oh no, no, no, no, no, no, no. Well, there’s the commission, and there’s this, and I haven’t gotten this, and I’ve only been here five months.” It’s like you make 140K, own it. Watch this. Ashley, how much money do you make per year?

Ashley: [00:39:26] 140K.

Ramit Sethi: [00:39:28] Great. How do you feel about that number?

Ashley: [00:39:30] Great.

Ramit Sethi: [00:39:31] Yes. Do you know, five minutes ago, you said it feels like $3 to you?

Ashley: [00:39:36] Yeah.

Ramit Sethi: [00:39:37] Because your mind is still in the land of being unemployed. You’ve got to change that. 

One of the biggest problems in all of money psychology is being able to effectively turn the page. There are people like Ashley who used to earn very little, and when they start earning more, they simply cannot turn the page and acknowledge it. They continue to be cheap, or worried, or live a scarcity-based life playing on defense, always wondering what can go wrong. And then, there are people who earn a lot, then something happens, like a job loss, and they refuse to turn the page by cutting their spending. They, too, are living in the past. 

My wish for you is to truly understand that with money, there are different seasons of your life. If you’re young and you have no money, embrace it, find cheap ways to travel, be okay with living in a small apartment with three roommates, whatever. I look back on my early 20s, and I love that I backpacked across Europe, and I ate at Taco Tuesdays, and I didn’t care about buying some expensive sweater. There are other seasons of life. For some, it’s getting married, having a family. For some other people, it’s developing finer culinary tastes. 

I love to stay at nice hotels and I love to eat street tacos. You can blend your seasons. But here’s the key, you must know what season of life you’re in right now and you must know what season of life is probably next. When you know those two things, that lets you be present today and it lets you set yourself up for success tomorrow. If you are living out of alignment, if you’re spending more than you actually have or you’re underspending on what you can easily afford, you’ll find yourself feeling nervous, and anxious, and unsettled about money like Ashley.

Ashley: [00:41:46] But it’s like I knew that we could, because we just went on this vacation and went to this dinner, and hat kind of anxiety about money has passed down to me a little bit.

Ramit Sethi: [00:41:59] How do you manifest that anxiety with money?

Ashley: [00:42:03] Hmm. Apparently, by getting into credit card debt. I was living in a world where it was very toxic in terms of Keeping Up with the Joneses, and consumerism, and materialism.

Ramit Sethi: [00:42:13] Specifics, please. What are we talking about?

Ashley: [00:42:17] Yeah, handbags, shoes, cars, vacations.

Ramit Sethi: [00:42:20] Tell me. I got to know the brands. 

Ashley: [00:42:23] Designer. 

Ramit Sethi: [00:42:24] Chanel. What else? Louis Vuitton.

Ashley: [00:42:26] Saint Laurent.

Ramit Sethi: [00:42:27] Yes. What else?

Ashley: [00:42:28] Gucci shoes, and Manolos, and things like that.

Ramit Sethi: [00:42:32] Okay. Good stuff. And were you earning enough to pay for these on your own?

Ashley: [00:42:36] Yes.

Ramit Sethi: [00:42:37] Okay. So, you were making good money, you were spending essentially everything you made on this fashion stuff.

Ashley: [00:42:45] That, dinners, trips.

Ramit Sethi: [00:42:48] Okay. And was there any consequence to this? Anything bad ever happened? 

Ashley: [00:42:55] No, not until I opened that first credit card.

Ramit Sethi: [00:42:58] Well, even today, has anything really bad happened to you?

Ashley: [00:43:01] Just the credit card debt. That’s it. 

Ramit Sethi: [00:43:04] Again, I’m going to ask, has anything really bad happened?

Ashley: [00:43:06] No, never been thrown in jail for it. No one has ever come after me.

Ramit Sethi: [00:43:08] No. I mean, look, you’re eating tuna tataki, it’s fucking great. Do you see that, deep down, you go, “Oh, my God, if I spend this money, I get these beautiful Manolos, and then if I spend more money, I get whatever bag or whatever trip, and yeah, yes, I know there’s this bad thing, this credit card debt over here”, but really, has it affected your lifestyle, whatsoever?

Ashley: [00:43:35] No, but I want to get rid of it, because as I’ve gotten older, and especially with COVID, the things that were material don’t matter as much to me anymore. Like I’d rather spend my money on trips and experiences, saving for our future and for a house, and all of those things are what are the most important things to me right now. I haven’t bought a bag in a few years or nice shoes in a few years, and I’m happy with that. Just for me, if I didn’t have that debt, the income that I have would be great and I could start saving again. Like at one point, I have like 20K in my savings that is depleted over the years based off of paying off credit cards, paying for trips, supplementing, not having a job over COVID.

Ramit Sethi: [00:44:28] I feel like you’re just really talking a lot to distract yourself. Do you even know what we’re talking about right now?

Ashley: [00:44:34] No.

Ramit Sethi: [00:44:36] What’s going on right now? What was my question?

Ashley: [00:44:39] I don’t even remember.

Ramit Sethi: [00:44:40] Yeah. What just happened was very fascinating. I asked you, have you faced any real consequences?

Ashley: [00:44:47] Oh, yes.

Ramit Sethi: [00:44:47] And here we are, 25 minutes later, with you justifying, “Well, in the past, I used to do this, but I’m totally different, and if I had no debt, everything would magically be great”. Do you really believe that’s true?

Ashley: [00:45:01] Probably not.

Ramit Sethi: [00:45:02] So, why are you bullshitting me?

Ashley: [00:45:03] I have no idea. It’s like the anxiety talking.

Ramit Sethi: [00:45:07] Why are you bullshitting yourself?

Ashley: [00:45:09] I don’t know.

Ramit Sethi: [00:45:11] You are going to bullshit yourself right out of this relationship. I only say that because both of you told me it was a 10 out of 10. And Josh, you literally said to me, this is make or break.

Josh: [00:45:25] I did. 

Ramit Sethi: [00:45:26] Part of a rich life is being honest. It’s being honest with yourself and honest with the people around you. That’s really, really hard to do, especially when you have some desires that might be uncomfortable or even unpalatable to your partner. Ashley, if you truly want Josh to pay for all dinners and you want to go out to dinners six times a month, okay, we’re going to put that out on the table, but then you need to be honestly prepared for if Josh is going to want to do that. 

More importantly, I don’t want you to just live your relationship out of fear of, what is Josh going to say? What I want to know is, what do you want, Ashley? What are you willing to change, because you told me it was a 10 out of 10? Otherwise, we’re just here dancing around and using all these words, and nobody even remembers what the hell we’re talking about. It’s a waste of everybody’s time. So, where should we go from here? Ashley, you tell me. What do you want to talk about?

Ashley: [00:46:33] I want to constructively talk about realistic ways for us to combat our debt. I mean, together, but obviously pay for our own. Try to see eye to eye on our views of money, so we can move in together, continue our relationship, and not have these fights about money or uncomfortable conversations.

Ramit Sethi: [00:46:57] Great. I’m with you. I think I can help. I love hearing that. Okay. Let’s talk about the numbers. You make $140,000 a year. When I look at the amount of debt you have, I don’t think it as insurmountable. I think that you could tidily pay this debt off. It would take you a little while, might take you a couple of years, might take you four, five years, depending on how aggressive you get, but it’s not that much. The way you talked about your debt, you talked about it like it was $350,000, 18K?

Ashley: [00:47:38] I know. I’m lucky in the sense that I am not someone that has $300,000 in debt, but to me, it’s still a lot of money to pay off.

Ramit Sethi: [00:47:48] It is a lot of money, but it’s also not what’s really keeping you from being successful with your rich life.

Ashley: [00:47:56] What is?

Ramit Sethi: [00:47:57] Well, let me put it this way. If you had 3K of credit card debt, you would still feel the same way. If you had zero dollars in debt, you’ll still feel the same way. And when you have $5,000 in savings and $10,000, you will still feel the same way about money.

Ashley: [00:48:15] And why is that?

Ramit Sethi: [00:48:17] You tell me.

Ashley: [00:48:19] I guess the financial anxiety.

Ramit Sethi: [00:48:22] Where does it come from?

Ashley: [00:48:24] From my family.

Ramit Sethi: [00:48:26] Mm-hmm. And then, they taught you what?

Ashley: [00:48:29] Scarcity.

Ramit Sethi: [00:48:31] Tell me more. What was the words they used?

Ashley: [00:48:35] We can’t afford this.

Ramit Sethi: [00:48:37] Do you think that maybe when Josh says, “Hey, we can’t afford this dinner”-

Ashley: [00:48:41] It’s triggering, for sure.

Ramit Sethi: [00:48:44] Uh-huh. And so, your reaction to that is?

Ashley: [00:48:48] To get upset. 

Ramit Sethi: [00:48:50] And then, do you go to the dinner and spend on it?

Ashley: [00:48:54] No.

Ramit Sethi: [00:48:54] Yeah, you do. You go.

Ashley: [00:48:56] I mean, I don’t, personally. He does.

Ramit Sethi: [00:48:58] Yeah. Right. “We go to dinner, and then he pays for it”, yeah. Okay. I want you to both talk to each other and I want you—I don’t need all the caveats and I don’t need all the, “Well, depending on this and that”, just tell me what is going to happen, whether it’s tomorrow or 20 years from now, if you keep this lifestyle up. Go ahead.

Josh: [00:49:19] We are going to end up, one way or another, not succeeding in our relationship, or one of us or both of us will be unhappy.

Ramit Sethi: [00:49:29] What does that mean in plain English?

Josh: [00:49:31] It means we’ll break up and no longer be together.

Ramit Sethi: [00:49:34] Thank you.

Ashley: [00:49:34] Yeah. If we keep going like this, we’re going to continue to fight about money, not get to our realistic goals, and break up.

Ramit Sethi: [00:49:43] This is a fascinating conversation. The thing I love about Josh and Ashley is that they are open. They’re being honest. I love that Ashley says, “Yeah, I expect him to pay for me”. Do you know how few people would be open and own how they feel? Now, that doesn’t necessarily mean I agree with her, but I just love meeting somebody who’s open about what they believe. Josh, he’s feeling the frustration, because he goes, “Why? It doesn’t make any sense. We basically make the same amount of money. Can you please explain it to me?” 

And now, we start to get into all those soft, squishy, invisible scripts about money, about gender, about how we were raised and what we experienced before. These are the kind of things that nobody wants to talk about publicly. They all happen behind closed doors. That is why I started this podcast, because I want to show you that these conversations are happening and it’s not just you. 

So, what have we learned so far? Yes, they both have different beliefs about money. We’ve also learned that they have high incomes, but the way they talk about their incomes is fascinating, interesting, also troubling. They are now starting to realize why they haven’t paid their debt off yet. Okay. It’s not just math. In fact, this isn’t a math problem. It’s much deeper than that. And in part two of this conversation, next week, we are going to get into the fascinating nuts and bolts of how to change their views of money. Be sure to stay tuned because you will be fascinated by what happens next week. 

Thanks for listening to I Will Teach You To Be Rich. I’m Ramit Sethi. Please follow the show on Apple, Spotify, or wherever you listen to podcasts. If you haven’t read I Will Teach You To Be Rich, my book, pick up a copy. You can get it at any bookstore or any library, and it will show you this specific tactics for how to build the I Will Teach You To Be Rich system into your personal finances.