Love & Money: 5 Awkward Questions Answered (feat. Ramit Sethi)

I find one topic almost no one wants to talk about is money.

So in this week’s video, I sat down with my good friend Ramit Sethi, bestselling author and CEO of “I Will Teach You To Be Rich,” to learn exactly how to have these difficult conversations so you can feel happy and secure about money in your relationship…

What’s the one piece of money advice you found most useful?
Leave your comment below…

Matthew: I am here today with a friend of mine. A special guest. His name is Ramit Sethi. CEO of, I Will Teach You To Be Rich, and he’s right here.

Ramit Sethi: How you doing?

Matthew:I’m good.

Ramit Sethi: Thanks for having me.

Matthew:It’s exciting… This is…We always meet for like dinner.

Ramit Sethi: I know.

Matthew: And we never have met on camera.I love this. Is this our first time being on camera?

Ramit Sethi:  Ah… Yeah.Wow. This is a first.

Matthew: I know.

Ramit Sethi: I can feel the energy.

Matthew:I’m nervous. [Laughter] So here’s what I did. I put out the word on Instagram to say I’m gonna be talking about money in the next video.Money in relationships. Money in dating.What do you wanna know?Here’s what you had to say, and I’m just gonna fire these questions at you, Ramit, I love it. and let’s see where we get to. 1.If he can’t financially provide for a family, should you proceed with the relationship?

Ramit Sethi: My god… They’re really…

Matthew: Did you know I’d be putting you on the spot to this extent?

Ramit Sethi: I’m sweating.It’s fifty degrees, and I’m dripping in sweat.I think the politically correct answer is that…Of course, you know, there’s more to life than just financially providing, but I think we should be honest. I think that for many people…your financial wherewithal is an important consideration in a relationship, and we should be honest.Now should it be the only thing? No, of course not, but if you think about the kind of lifestyle that you wanna lead, and that you wanna lead jointly with your partner.That probably involves money.That involves maybe living in a certain place.It involves how many kids you wanna have, what kind of school are they gonna go to, and activities?That takes money, and I think we should instead of putting our head in the sand and saying, ‘Love is enough. ‘ Love is important, but it’s one part of a relationship, and finances are really important.If you expect to live a certain type of lifestyle, and that’s what you envisioned your whole life, then the partner that you choose needs to be aligned with that.

Matthew: Or you need to be prepared to re-evaluate your vision.

Ramit Sethi: Exactly.

Matthew: For the life you thought you’d have, right? If love really is enough, Yes. If love really is enough, then it’s enough to re-evaluate your entire blueprint for the life you thought you’d have.

Ramit Sethi: Absolutely, and there’s a lot of that to be said.When you get into a partnership, when you get into a serious relationship…The vision you had for your life will necessarily change.It has to, because now you’re a team, you’re not just one.That’s okay.I actually look forward to that. I welcome that, but you do not want to be bringing resentment into a relationship.You wanna be confident and comfortable with what your vision is, and make sure that you’re on the same page.

Matthew: Yeah, and we’ll probably summarize that by saying, either change your vision, or change the person.

Ramit Sethi: There you go. One of the two.

Matthew: 2. What to pay for on dates so that he won’t think you’re taking advantage of him. What things should he pay for?

Ramit Sethi: Okay, first of all, I just wanna say, you have the single best answer anywhere in the world on this question. Everybody go watch his video. It’s so good… About, should you pay for the date?

Matthew: Jameson, throw up a little clip of that.

If you go on a date with a guy, and you don’t offer to pay your share, you weren’t taught right. If you go on a date and he doesn’t pay, he wasn’t taught right.

Ramit Sethi: I love what you said on your video though.Making the offer matters, and I think after two or three dates…Like really making a strong offer and saying, ‘This one’s on me’. It goes so far… It goes so far, and I told my wife when we met and we started getting more serious… I said, you wouldn’t believe what it meant to me that you actually picked up the check after date number three or four. Like it meant a lot to me, and she was surprised. I don’t think she had realized what men’s perspective on this is.

Matthew: Well, I think that is the danger…Is that it’s such an intensely, awkward subject for a guy to even bring up,

Ramit Sethi: Oh yeah.

Matthew: For a guy to even bring up that he’s far more likely just to hold on to this resentment about it that’s gonna come out later down the line, or even decide to stop going on dates with this person altogether, because he feels taken for granted.

Ramit Sethi: Yeah.

Matthew: 3. Is it better to have separate bank accounts, and pay for things half-half, or have one joint account to pay for things with?

Ramit Sethi: Both. What I would recommend for everyone is have a joint account where you combine some of your finances, and that would be things like, maybe your mortgage, or your rent, groceries. Things that are joint expenses. From that you also have your individual accounts.That’s money you can take, and spend on whatever you want.No questions asked. It’s your discretion. Go and enjoy, and you can discuss how much goes in each account, but I think it’s important to have a joint unit, and individual units.

Matthew: I like that.So you have a sense of togetherness about something, but you don’t lose that sense of independence in what you’re doing financially.

Ramit Sethi: Exactly.

Matthew: 4.How do you tell a potential partner that you have a lot of student loan debt without making them run the other way?

Ramit Sethi: That’s a good one.

Matthew: I guess that we could apply that not just to student loan debt, but you know, anyone with credit card debt, or any kind of financial baggage.

Ramit Sethi: Yup.

Matthew: How do they communicate that?What responsibility do they have to communicate that?

Ramit Sethi: They definitely have a responsibility.If you’re getting into a partnership, you gotta put it all out on the table, and the way to do that without freaking your partner out is number one, to be proactive.Don’t wait for them to be knocking on the door, and saying, ‘Hey… Like, I have a feeling there’s something not good here… ‘ .That’s a bad place to be.So be proactive, and the second thing is to be calm, to be forthright, and then to tell them your plan.Now notice in order to get there you have to do a lot of work, like ninety-five percent of the people who write me with debt don’t even know how much they actually owe. So to have this conversation means you need to get straight with yourself first, and you need to be confident. That takes some self work before you go and have the conversation with your partner.

Matthew: I really like that. I like the idea that you’re proactive. I like the idea that you bring a confidence to the plan. I think that’s the key, is that you’re…Look, we all find ourselves in difficult positions at one time or another in our life.Things don’t always go to plan, but if we come to someone saying…To me… I always say the same thing to women about if you have a job you don’t like. You don’t have to, you know…Is it more attractive to be doing a job you love? Yes, but you don’t have to be doing a job you love right now. If you do a job you hate right now, you shouldn’t talk all day about the job you hate.

Ramit Sethi: Yes.

Matthew: You should talk about your excitement you should talk about your excitement about the transition you’re trying to make.

Ramit Sethi: Absolutely.

Matthew:Talk about the plan, and so I like the idea that no one’s perfect. You might come to a relationship with debt, or you know, financial issues, but if you can confidently say, here’s what I’m doing about it that, A. Confidence, and B. The perceived competence in you dealing with it.

Ramit Sethi: Yeah.

Matthew: That becomes attractive in and of itself.

Ramit Sethi: Exactly.

Matthew: 5.In a world where men still often are seen in the role of provider and leader, how can a woman financially contribute without hurting a man’s ego? Especially if earning more money than him? I feel like one of the times that, that practically comes up is when the partner earning more money wants to do certain things.

Ramit Sethi: Yup.

Matthew: and you know, wants to take that spontaneous trip somewhere, wants to go and stay in that hotel, wants… And their partner isn’t able to just make that decision to go, and I think probably, culturally speaking that’s harder for a woman who just decides, ‘I wanna go and do this. ‘ and he’s thinking, ‘I can’t. ‘ ‘I don’t have the means to go on that trip you wanna go on. ‘ Do you think in that sense the woman should just…Okay, she wants to go…She just pays, because she’s got the means and he hasn’t, and doesn’t make a big deal out of it? And says, ‘You know, I wanna go, and I don’t mind taking care of it. Let’s go. ‘ What do you think?

Ramit Sethi: I think that first of all, that situation’s complex for either party, man or woman if the higher earner just wants to go somewhere on a whim, but there’s an added layer of complexity with the cultural narrative of it being a woman who has more money.So we should just acknowledge that.That’s a new thing, and we should acknowledge that, that’s tricky for anyone. With that said, if you have the financial wherewithal, and you’re comfortable paying for your partner, that person’s your partner. I think that’s perfectly reasonable. I do love what you just offhandedly said. You said, “Should they not make a big deal out of it?” So much of making finances work is actually not making a big deal of it. Notice I’m not coming to you… ‘Ah… Excuse me, I have this question that makes me really nervous,and I’ve been agonizing over it… ‘ Of course that person’s gonna detect your energy, and they’re gonna get defensive, but if you say, ‘You know what? I’ve been thinking. I really loved how we spent time together two months ago in Italy, and I would love to take a trip to Thailand this December, and I was thinking that I would make it a treat, and we would have a great time. What do you think about that?’

Matthew: Yeah, I think that’s interesting, because there’s… I also think as much as people can come with a timidity about that kind of thing, they can also come with a…Their… From either man or woman…When someone earns more money it’s very easy to it’s very easy to inadvertently bully someone with that.

Ramit Sethi: Like what would they do? What’s an example?

Matthew: I feel like there are times when instead of making little of it, and being like, ‘Don’t worry about it. I just think it would be fun for us to go. ‘ There’s the sense of people almost putting it in someone’s face. ‘I’m doing this for you. ‘

Ramit Sethi: Ah, yeah that’s toxic.

Matthew: ‘I’m doing this for you. ‘ Or even bringing it up at a later date.You know… ‘I’m the one who paid for that trip. ‘ ‘I’m the one who… ‘ It’s very easy when someone has means to kind of psychologically or emotionally bully someone psychologically or emotionally bully someone about that to make them feel less than, because you’re doing it for them.

Ramit Sethi: You have to acknowledge these dynamics.You have to be thinking about this, and that’s just the cost of your success. The cost of your success means you now have to think about things that you didn’t used to have to think about.

Matthew: That was great man.

Ramit Sethi: I loved it.

Matthew: I enjoyed that.

Ramit Sethi: Thanks for having me. That was awesome.

Matthew:I think that was super useful. I’m excited to see what you think. Why don’t you leave us a comment… Let us know what’s the one piece of advice from everything we just talked about that you feel is most useful, and relevant to you right now. Leave us a comment, and go check out Ramit’s site as well. He is at, I Will Teach You To Be Rich, and what’s your Instagram?

Ramit Sethi: Ramit, @Ramit

We’ll see you soon.

Thanks guys.

9 Texts No Man Can Resist

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