Dan Morrell: Which is the best dating app? Can money actually buy love? When do you talk about money in a new relationship and how do you broach the topic? How can well-meaning parents actually help their still single adult children improve their chances of finding a partner? Rachel Greenwald (MBA 1993) is a celebrity matchmaker, an executive fellow at HBS, and a New York Times bestselling author of two books about love and relationships. In this episode of Skydeck, which was taped in front of a live audience at this year's fall reunions and hosted by our own Jen Flint, Greenwald gives the audience a glimpse into the world of professional matchmaking—and answers all of those pressing questions and more.

Photo by Ann Hermes

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Jen Flint: Let's talk about how we talk about money. And you work with your clients to coach them through these conversations around money, particularly in a new relationship. Share with us some insights about the things that go wrong in those discussions and how we can put ourselves on a better track.

Rachel Greenwald: There are a lot of different ways to think about conversations around money. Maybe it's helpful to start with this framework that people may not know about.

Many people might be familiar with Gary Chapman's five love languages. This is a parallel framework called four money languages. And it's essentially what money means to you and what your relationship is to talking about money. So the four money languages are where money means success, security, affection, and acceptance. For example, if a couple is going to buy a car, one person in the couple wants to buy a Porsche and the other one says, no, let's buy the Honda Accord. On the surface, you might think one's a spender, one's a saver or one is extravagant or one's frugal, but that's not even the tip of the iceberg.

The four money languages really help you understand what money means to the other person, psychologically. And a lot of that has to do with their beliefs in childhood around money. If the person in the couple wants to buy the Porsche, their money language is success. And so the Porsche is a symbol of how successful they are in the world. It's not necessarily that they're an extravagant spender, but the purchase is deeply tied to their ego. And so if their partner's money language is security, then their desire to buy the Honda Accord is really more about their values around budgeting and saving for the future.

So there's a famous psychologist named John Gottman – you may have heard of the Gottman Institute and he has a book called Eight Dates. It's a guide to having eight different conversations around certain topics; and one is the money date. He recommends going out to dinner with your partner. You can do this around the dinner table with your kids or your grandkids as well. And each chapter in the book has a list of maybe 50 to a hundred questions that you can ask to really understand how somebody is thinking about money. How was money discussed in your home when you were growing up? Or what's your most painful memory around money? Things like that. And it really brings out this deeper layer of your attitude towards talking about money to help somebody understand why you behave certain ways around spending or saving. And that's very helpful in any kind of relationship, especially in families. So I guess that's the way I would start to think about that.

Money is a source of great conflict in relationships of all kinds. And it's usually never about the dollars. Conflict around money is about what it symbolizes. Whether money means power or trust or freedom. These are the deeper psychological concepts that you really want to understand so that you can better talk to somebody in their money language and try to avoid those conflicts that arise when you don't understand what the money is symbolizing for the person.

JF: One question that we did promise the audience to answer is whether or not a person can actually buy love.

RG: The age-old question, can money buy love? Or sometimes it's phrased as, can money buy happiness?

I think there's an automatic response that most people have, which is, no money can't buy love or no, of course, money can't buy happiness. But I think about it as much more complex than that. I think that money can help you buy love, and money can hinder you to find love.

So what I mean by that is that it can help make the process of finding love more efficient. And so concierge services like matchmakers or dating coaching or consulting services, they're very expensive. It's a luxury good that you can buy to make it more efficient, so that when you show up for an actual date, you are not jaded or cynical or frustrated or tired because the process today can be very time consuming, and really zap your energy. A lot of people who date online will say that it's like having another full-time job – there's a lot of messaging, there's a lot of ghosting, there's a lot of fall off in communication. So money does help make the process more efficient in finding love.

But on the flip side, money can actually hinder a lot of people from finding love. The way that happens is that I think there's a mindset among wealthier people that they are always looking for the best. They want to buy the best. They have a mentality of optimizing. And that mentality creeps into their search for a mate by thinking about sorting through their potential choices of someone that they're going to date through a more superficial lens. They might search initially on attractiveness or status or education level. And it's harder to unpack what they really need to make them happy, versus what they think they want on a list of criteria.

I have an exercise that I do with clients in the beginning of any relationship that I start with them, and it's what I call a basement penthouse exercise. And a client will initially fill out a long questionnaire talking about many things about their background. And one of the things I ask is, what are you looking for in a partner?

People will start to write things like a certain religion or geography or a certain height or background. And so I file that away. And then they come to me in the first meeting and I say, before we even talk about romantic relationships, I want to understand more about you and what makes you happy. So think about a person in your life who genuinely makes you happy when you're around them. It could be a friend or family member, it could be your college roommate. It could be your HBS section mate, anybody. Who's the first person that comes to mind that really makes you happy?

And so somebody might say. Oh that's easy, It's my sister. I'm like, oh, tell me more about your sister. So they'll say things like my sister is just the funniest person I know. She's not judgmental, she has really a kind heart, and they start listing. So I've made notes about this and then I whip out their questionnaire that they answered a few weeks ago and I turn to question five where they said what they're looking for in a mate. And I said, look at these two lists, they're vastly different. What you're looking for in a mate is a height and a religion and a geography and an education background – that's what you want. But look at this list that makes you happy. The person that makes you happy has a sense of humor, isn't judgmental, and so forth.

And I tell them that the gap between those two lists is what is preventing them from finding true love. And merging what they really think about as their needs, and what leads to their happiness is often the breakthrough moment that they realize, okay, I've been looking in the wrong place for love. And so in that way, someone who's very wealthy and optimizing and trying to buy the best, can often miss out on what actually is going to make them happy.

JF: Do people manage to close that gap? What does that work look like?

RG: Often it's just something that never occurred to them. They never thought about it. And especially in this environment, HBS alums, I think that we've been on a path often for status or success or achievement. And we never really step back and look at whether those things are correlating with our happiness.

So there are a lot of sessions this weekend at reunion about happiness and crafting your life and finding joy in the third chapter of your life in many of our cases. And I really think it's just about taking the time to pause and step back and asking those questions. I don't think it's a skill that people don't have, I think it's a muscle that they don't use often enough. So usually people can switch off like that and really start to focus on something different, once they're made aware of it.

JF: Speaking of asking questions, I think this audience is going to have a lot, perhaps there's some parents in the audience with some questions for you. But for those of us who may know someone who is looking for a partner and hasn't found that person, what advice do you have? What can we do for that person?

RG: I bet every single person in this room knows somebody, whether it's yourself or your friend or a family member who is looking for love. And it's probably really frustrating not being able to help them because if you knew somebody to fix them up with, you would. Or if they would let you, you would. So I think the best thing you can do for somebody that you really want to help find love, is to give them a gift certificate for a professional headshot. And it's a small thing. It might be a couple hundred dollars. But in today's world, your photo online (as superficial as this sounds to a room full of smart, accomplished people), is probably the simplest change you can make.

And so give somebody (for the holidays this winter or for their birthday or for no reason at all), the gift of a professional photographer. Because everyone is Googling you or making snap judgments about you from your dating profile, from your LinkedIn profile, and I think too many of us don't pay attention to having a high-quality photo.

So find a photographer in the person's city to just go out and give them the gift of photography. Because that will make a huge difference in connecting you either to a romantic relationship or potentially even your next job. Even employers care about whether your photo is good, in all the dimensions that might mean for the environment.

Carol Lee Heilemann (MBA 1983): My name's Carol Lee Heilemann. I'm in class of 83. You alluded to several websites, and I was wondering if there are certain ones that are really well known, like Match.com and eHarmony?

RG: People ask all the time, what's the best site or what's the best dating app? And this is the truth: you have to be on three. Every single one has losers, jerks, weirdos, and creeps. And every, as well as, every single site has gems and wonderful people. So don't get hung up on choosing the best site, because there is no one best site. You need to be on three. It's a lot of work, but you can hire an online dating concierge, and they can do the work for you.

By the way this is sort of a sub industry within the matchmaking world, where somebody basically impersonates you on your dating profile. So they create your profile and they use your photos, they interview you, and create a profile that sounds like you. And then they manage the profile, because it's a full-time job.

These people have desks that are littered with burner phones. And so every client has their own phone number. They're on Match.com and Bumble and Hinge and the Right Stuff, and all these other sites. And they are messaging for you and swiping for you. And their goal is just fine tune the top of funnel. Because it's so much work to correspond with people in the beginning stage, a lot of people drop off, and they just want to convert the initial interest into setting you up on a phone call or an in-person date as quickly as possible.

So you may not even be talking to the actual single person when you're messaging them. And again, this may sound terrible to most people, but this is the world we live in. This is the reality of dating at any age today. And so you can complain about it, but you also have to accept that's how it's done.

In the business world it's like saying, I really want a job, but I refuse to have an email address. So if you want to contact me, you're going to have to find me. It's the same thing. It's just the reality. So if you can afford it, hire an online dating concierge to do the work for you. They'll put you on three sites. I'm not saying it's going to be easy; I'm saying it's going to be worth it. And the goal is to get off the online dating sites as quickly as possible so that love can actually start in real life, and you meet somebody in person.

Skydeck is the Harvard Business School alumni podcast, featuring interviews and insights from across the world of business. It’s produced by the External Relations Department at HBS. Our audio engineer is Craig McDonald.

It is available on Apple, Spotify, and wherever you get your favorite podcasts. And If you could take a moment to rate and review us, we’d be grateful.

For more information, or to find archived episodes, visit alumni-dot-hbs-dot-edu-slash-skydeck.

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