Couples, Money, and the Future of Dating Apps

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Evan Engel: Hey, Pivot listeners, this is Evan Engel. I'm a producer on the show with a quick heads up. Today's show is spicy. It contains mature adult themes and is not intended for younger audience members. Thanks for listening. Enjoy the show.

Kara Swisher: Hi, everyone. This is Pivot from New York Magazine and the Vox Media Podcast Network. I'm Kara Swisher.

Scott Galloway: And I'm Scott Galloway.

Kara Swisher: So today, Scott, we're bringing you our first dating show to our listeners. I cannot believe it. We've been asking you to send in your questions, which have been great. But don't forget, dating is a $6 billion industry in the U.S. We'll have predictions from experts on the business of romance as well. A quick note, some of our listener questions have been edited for length and clarity. But here we are in our new job as Yenta One and Two. What do you think about that?

Scott Galloway: I think it's very similar to those infomercials with Cher talking about hair care products as she wore a wig. I think us talking about dating is going to be entertaining. I don't know how useful it's going to be. And also, we're already off to—we already have misinformation. It's not a $6 billion business. It's a $6 trillion business. And that is every time you buy a Ferrari, every time you buy AirPods and Apple, anything that any consumer product that has irrational margins is a function of two things: either wanting to feel closer to God or wanting to be more attractive to the opposite sex. Even if you're in a monogamous relationship, I will continue to spend irrational amounts of money on things like Range Rovers and Panerais because I'm hoping for a random sexual encounter, because that is what my instincts are telling me.

Kara Swisher: Okay. Well, I want to know what it says about my Kia. That's what I want to know.

Scott Galloway: It says that you've given up. It says, "I'm done." It says literally, "I surrender." I had a Honda minivan in my 20s. Look, this is how the Subaru—I think about this a lot because I teach the kids and the kids are horrified, and one will get outraged and send a message to the dean and the dean's like, "Shit, again." But I think the majority of high margin consumer value, whether it's Apple, whether it's LVMH, is a function of two things. Men feel an obligation to spread their seed to the four corners of the earth. And women feel an obligation to put up a much finer screen and pick the smartest, fastest, and strongest seed. And all marketing.

Kara Swisher: All right, seed. Please stop saying that word. But go ahead. Move along.

Scott Galloway: Okay. My swimmers. What do you want me to call it? My man gravy. What do you want me to call it?

Kara Swisher: I love this show already. Oh, my God. Why did I even bother?

Scott Galloway: Because it got worse. I don't care if anyone gets anything out of this. I'm enjoying this.

Kara Swisher: Go back to speed. Okay. Let me just say I'm enjoying this show a lot so far. Should we just read out now? Thank you. Today's show was produced by Laren Aiman. Thank you, Ernie. Why don't you take it from here before? It's our first and last episode.

Scott Galloway: Okay, Scott, let's kick it off with a question that came in via email. I'll read it. Hi, Kara and Scott. I'm a 24-year-old male. My boyfriend and I are constantly sending each other small amounts of money back and forth for meals, drinks, rides, etc. We make an effort to share the cost for things like hotel rooms and flights, but also for smaller purchases. We've been dating over a year now. It feels like we're sending the same $20 back and forth over and over again. How do you decide who pays for what, particularly when you're in a same-sex relationship? And when you're not married? Love the pod. Adrian.

Kara Swisher: Adrian, honestly, just pay for things. I do not do this. I pay for as much as I can. I don't like to think about money. And I know a lot of people do. And I hate it. I hate that. I hate trading money back and forth, "pay you back for things." I hate it. I think it's bad for a relationship.

Scott Galloway: I think that where you want to be around money in a relationship, and also with your emotions—the same approach to your emotions, the same approach to time, the same approach to money—should be generosity. Fight for the check and don't keep score. By the way, if at some point you recognize that I'm always paying for everything, I have friends like that that always seem to reach for their wallet after I've paid.

Kara Swisher: Yeah. And by the way, people notice.

Scott Galloway: Yeah. But I realize I just bragged there, but bust out of that bullshit.

Kara Swisher: Yeah. Both of you, "All right, I'll grab this, I'll grab that." Just get out of the Venmo thing. You're in a relationship. It's a hassle.

Scott Galloway: It's a hassle.

Kara Swisher: Yeah, it's an interesting thing. For a while, after we had the two kids, in the two relationships I had, Megan, before she went to Google, did not have a lot of money. She worked for Planet Out, and I ended up paying for a lot of things. But I don't think I kept track of it. It was not even a thought. We were married, and then she made a lot of money. And then, I don't know, we both paid for things. We never really talked. That was one of the great things. We didn't talk about money a lot.

Scott Galloway: And then she left you for Jeff Bezos' girlfriend, right?

Kara Swisher: No, no, no. That would be good. I'm not getting into what happened in my relationship. But nonetheless, with Amanda, she's worked her whole life. She had a job at CNN. And then when we had the kids, I was making more money. And it was easier for her to stay with the kids, especially over COVID. It was harder to get help. You need help if you're going to work or have daycare or whatever. That wasn't available because of COVID. And she stayed home. And I know she was uncomfortable with taking money from me. And what I tried to do was never mention it. I hate thinking of money because if I make enough, then it should be fine. My mom had a lot of money issues and it bothered me that they were talking about cash. So I know she was uncomfortable. Now she's working again. But I feel like talking about money is just the end of relationships. It just is.

Scott Galloway: Well, I understand what you're saying, but I'll push back. When your relationship—first off, they're dating. It sounds like if they're both making about the same amount of money, they should just give themselves a break and say, "All right, let's trust each other to just grab the bill on a regular basis."

Kara Swisher: On a fair basis, yeah.

Scott Galloway: On overtime, it should even out. And if it isn't, it's fair for one person to say, "I noticed I'm just paying for more. I need you to pay for more." But this Venmoing back and forth... I think it's important at some point to have a broader macro conversation if you're going to get serious and you guys are thinking about marriage. What is our approach to money? What is the economic class, weight class we expect to be in, who's responsible for maintaining that weight class? Also, what causes a huge amount of stress in relationships is people's approach to spending. I have a close friend who makes an incredible living and his spouse is psychopathic when it comes to spending money. This person will spend $1,300—I'm not joking—on flowers for a dinner party. This person is broken when it comes to money. So you need to have an open conversation around economics when the relationship becomes serious and you're thinking about partnering, because you want to partner economically. The economic health or lack thereof of your household is an enormous stressor if you're not on the same side on this.

Kara Swisher: That's fair. That is a fair thing. I just think people should—I will worry about money when I don't have it. When you do have it, talking about it is not something that I think is very good for a relationship. I don't like talking about money at all. And it's because I make good money. But if I didn't, I guess I would talk about it then. But until then, try to be generous, Adrian. But stop the Venmo. Stop the Venmo. It's weird. It's not sexy.

Kara Swisher: Okay, Scott, this one comes from Kristen via email. "I'm a single mom of a year and a half year old and a four year old. My husband left me last year. Kara, how do you approach dating as a single mom? And how do you think about a potential partner and also potential parental figure to my kids?"

Scott Galloway: Oh, that's a good question. I was not single very long, but I think it's really important to think about someone who does get along with your kids. It's my number one issue when I think about people I'm dating. I got married pretty quickly to Amanda after I met her. But I knew she was great with my kids. There's always going to be problems between kids and their step parents. But it's really important to make it the number one issue. I think it's been my number one issue. Scott, what do you think?

Scott Galloway: It triggers a lot of emotions. I was raised by a single mother. I physically remember at the age of 10 or 11 when my mom would have dates and these guys would show up and I'd open the door. I don't think I was being insecure. I remember registering that they were like, "Oh, fuck, she has a kid." I just didn't get the sense they were happy to see me.

Kara Swisher: Right, right.

Scott Galloway: Having said that, my mom had some wonderful men in her life that were very good to me. They were very generous. They took me on vacations with them. Look, I'm not here with a message of hope. I think it's really difficult with two young children to find—let me fast forward and be very honest. When I moved to New York and I was in my late 30s or mid-30s and single, all of these women I meet would say, "Oh, we know what to do. We're going to set you up with our hot, interesting friend who has a kid." And I wasn't interested, because I remembered how—I know that's bad. I'm just being very upfront. I remember not how heartbroken I was but how upsetting it was when my mom would go out with someone and then it wouldn't work out. I thought, "I don't want to—if this works out, I don't want to break—I don't want to establish a relationship with a child." Maybe that was immature. Maybe that was not very nice of me. But I think it's difficult. What I would suggest is try and put yourself in an environment where you meet men who are in a similar situation who also have kids. There's just no getting around it. It is an obstacle, a barrier, and not an asset—a liability in the eyes of a lot of men. Try and put yourself in a situation where you can meet single men who also have kids.

Kara Swisher: That's a correct answer. It's hard because there's usually another partner around, another parent that you have to also manage. You joke about us all the time because Megan's around and shows up. You have to have a very tolerant partner who realizes you have a bigger life. Amanda's amazing that way—you've had a bigger life before them and you have other people that have to stay in it. Everyone jokes, "Oh, another lesbian family," with all the exes and the partners of the ex. But it's critically important to have that happen. You have to realize what you're getting into if you're going into it, and what you are offering to people. Because there'll be another—your ex-husband is going to be a part of this too. Hopefully he's still involved in your kids' lives. But it's hard. I'm thinking about a friend of mine—I'm not going to say her name—but her husband left her in a really unpleasant way for another person at work, younger. She had upended her life—she had a very promising career and had upended her life to have a kid. She got sort of left high and dry. One of the things I always admired about her is she always made sure her child had a good relationship with her ex-husband. Honestly, I would have pushed him off a bridge. But she never downplayed him. She made sure that her daughter had a good relationship with her ex-husband. Later, things got better, I guess. It was quite tense for a while. But she never showed it. It's the same thing when you're bringing in another partner—you've got to figure out a way where you all get along with each other. And it doesn't happen all the time.

Scott Galloway: Well, I love this show already because it's bringing up all sorts of opportunities for me to talk about me.

Kara Swisher: Okay, good.

Scott Galloway: But I had the opposite experience and it really speaks to your point around distinctive your relationship. Let me back up. The most important decision you'll make is not who you marry. It's who you decide to have kids with, because you can get—if you're not married, so I've been married before and I got divorced, but we didn't have children. So it was a really expensive breakup. When people get divorced with children, it's just an entirely different level, especially if you're not economically secure. So the most important decision you'll make is not getting married. It's that decision: "Am I going to actually have a kid with this person?" Because you're in each other's lives one way or another for probably the better part of a quarter century. It also puts the woman at a disadvantage because women have to bear the child and take a disproportionate amount of responsibility for the child. I don't care what anyone says. It always ends up being the women—80, 90% of the time, the woman takes more responsibility for the child's well-being on a day-to-day basis. Going back to when my parents got divorced—my parents aren't bad people, but they're not very sophisticated. This is not an exaggeration. I'm nine years old. My dad's picking me up. My mom wouldn't go out even because she didn't want to see his car. So I'd have to walk out there alone. She would say to me, "Tell your father if he doesn't pay his child support by Friday, I'm calling his boss." So I'm nine delivering these messages. Then I deliver the message on a Sunday night because I've been digesting it in my stomach all weekend. And my father would say, "Tell your mother just because of that, I'm not sending the child support." When you weaponize your children against the other spouse, you are really showing a tremendous lack of character. I sort of forgive my parents because they were raised in such terrible circumstances. My point is, this is a back-ended way of saying kudos to her. Regardless of the animosity, your relationship between your ex is one thing, but you are really smart and you're doing the child a favor by keeping that shit out of it and trying to promote a healthy relationship between that kid. My parents did not promote a healthy relationship between me and the other spouse. And it really scarred all of us. I think that demonstrates a lot of character on your friend's part that she said, "Okay, I'm not going to contaminate their relationship." It shows real generosity and concern for the kid to try and promote a healthy relationship.

Kara Swisher: Exactly. At the time I was furious on her behalf. But one of the things that's really important—I think about that all the time, because you have the same arguments with your ex in that regard. Often I will get into little fights over lots of different things, because you have so many interactions about money and school and all kinds of trouble.

Scott Galloway: Parenting, right.

Kara Swisher: So recently I've tried very much harder to be nicer. I realized that I can be short-tempered. Megan was actually in New York also, because Alex was going away.

Scott Galloway: Megan, your ex, just to clarify.

Kara Swisher: Yes, and we all went out to dinner with my mom. George Hahn went. And I have to catch myself not to be short-tempered. I don't succeed all the time, but I think we both have to do that. Because it really does have a bad effect on kids. But the most important thing is that. And then also picking a partner who understands how important your children are. They're number one. You don't like to say it, but everything rises and falls on them on some level. Anyway, I feel bad for nine-year-old Scott right now. I'm feeling very sad for nine-year-old Scott, and I'm going to be very angry at your parents right now, if you don't mind.

Scott Galloway: He grew up to co-host a top 200 podcast, Kara.

Kara Swisher: All right, Scott, let's go on a quick break. When we come back, a prediction from author Logan Ury.

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Kara Swisher: Okay, Scott, we're back. The next one is a two-parter. First, there's a prediction from our friend, author Logan Ury.

Logan Ury: Hey, Kara, Scott, it's Logan Ury, author of *How to Not Die Alone* and director of Relationship Science at Hinge. What's next for dating apps is trying to bridge that gap between the two-dimensional profile and the first date. Apps are going to make it easier for daters to see what a potential match is like before they actually meet up. Hinge is already doing this with their voice prompts. If a picture is worth a thousand words, imagine how many your voice is worth. You can record a 30-second voice prompt to offer a glimpse of your personality. For example, my friend has a dry sense of humor. He uses the voice prompt, "How to pronounce my name," and his response is, "Joe." Some people think it's hilarious. Others ask if he really believes they don't know how to say his name. Either way, it's a great filter.

Kara Swisher: Oh, that's interesting. And we've got a listener question that's a great follow-up to that. I'll read it. "I'm a 28-year-old woman living in Brooklyn. I've noticed I tend to swipe right on men who have a clear style in the way they present their photos, their answers to questions on Hinge, et cetera. This kind of feels like a personal branding that we're told to seek out in our careers, but it kind of feels weird in a romantic world. Is capitalism ruining dating?" Wow, those are both two very good questions together. Thanks, Christine from Brooklyn.

Scott Galloway: Well, let me start on the first one. I think I like the voice prompt idea because I do think people are very performative in these dating apps and you really can't tell. The more you learn about them, usually it's via text. I've never used a dating app, I'll be honest with you. But I think feature-rich dating apps are not necessarily game-like, but feature-rich are good. The more you can get to know someone, the better. I know people stalk each other online. I know I stalked Amanda and she stalked me. I don't mean it in a negative way. We looked up each other. We saw things and tried to find things. I remember she had written a few tweets that I thought were very funny. I wanted to see more before I met her. We both did that. What do you think, Scott?

Scott Galloway: Anytime innovation or a sector becomes digitized, the primary fact or one of the primary facts is consolidation. One e-commerce player ends up having 50% share. One search engine, 93%. One social, 75% of all of it. The same thing is happening in dating, online dating. Everyone talks about income inequality. One of the biggest trends, and unfortunately I think it's a terrible thing, is mating inequality. Because Tinder is very two-dimensional, fewer people have a shot. Everyone wants the same 10%, especially with men. If you're a man and you can signal certification—"I went to MIT or Harvard"—you can signal wealth—"This is my zip code. By the way, accidentally my Rolex somehow showed up in the picture." That person, if there's 50 women on Tinder and 50 men, the vast majority of women will show all of their attention to a small minority of men, leaving the vast majority of men fighting over a small minority of women. There's huge mating inequality at the hands of digitization.

Kara Swisher: Because of branding, right? Because of personal branding, you're saying.

Scott Galloway: Well, not all that. The wonderful thing about human sexuality is it's just so fucking random. Supposedly the way someone else smells is a huge turn on or turn off for people.

Kara Swisher: Yeah, that's how I felt about you. But go ahead.

Scott Galloway: Thank you very much. So smell, a lot of that vibe, a good rap. The one thing I do like about this feature—voice is really important. Men have more of a shot. And so do women. Although men have always been kind of one-dimensional in terms of what attributes they're looking for in women. Women are more multidimensional. A guy has a much better shot, including many of the men who don't get swiped right on on Tinder, if they have a good rap and a good vibe. I speak from experience here. When I was in high school and I was 6 foot, 130 pounds of bad acne, I learned how to be—and I really fostered and leaned into my humor. I found that if I could make a woman laugh, she would go to the movies with me. It's very hard to get that across in a dating profile.

Kara Swisher: Yeah.

Scott Galloway: I don't like—I think you do all of it. I see where it's going. There's no stopping it. But I actually think there are societal reasons to get out. I would say to guys—I coach a lot of young men—"Your Tinder profile just isn't going to be that compelling. You're trying to figure out if you should go back to college. You're an OK-looking guy. You're not a great-looking guy. It's just not going to be that compelling. But you know what? You're an interesting, fun guy. You have a nice vibe to you. You need to get out and demonstrate that vibe." I say this to my sons all the time. You got to get out and let them see you.

Kara Swisher: Honestly, I swear to God, it was—first it was something Amanda said on Twitter. It just struck me. The Joe thing would make me laugh. That would make me laugh. And there was another one. I'm like, "Oh." Sometimes even now she says something—last night we went to this movie about All the President's Men and things like that. She said something funny as an aside. The minute she said something funny, I thought, "You're pretty." I thought that in my head. For some reason, the humor made—she is a very pretty woman—but for something, I immediately saw pretty again. It was kind of interesting. I was noticing the connection between humor and attractiveness. I agree with you. I think it's really the kind of humor I like.

Scott Galloway: Women select men based on three criteria in terms of mating. The first, and we don't like to talk about it because it sounds politically incorrect, is resources. It's very instinctual. "I'm going to have babies at some point. I will be vulnerable when I'm pregnant and have kids. I want somebody who can provide and has resources so my kids survive." If you think that's offensive, there's about 10,000 years of research to support that. Number two, intelligence. Intelligent people can protect me better than stupid people. The best way to demonstrate intelligence really crisply is humor and cleverness. People with good senses of humor, people who are clever, are good storytellers and intelligent. That says your kids will be protected. The third thing is kindness. It doesn't matter how rich you are, how funny you are. If you're an asshole, women over the long term—maybe in the short term they want to have a fun weekend with you or kiss you—but over the long term, they don't want to mate with you because it shows that you're not a good person. Being clever and funny is an outstanding means.

Kara Swisher: Outstanding. Yeah. Not mean funny. Not mean funny, but very funny. You're just offbeat. Self-deprecating. I would go out with that Joe. "How do you pronounce my name? Joe." That would make me laugh. So one of the things, so what Christine was saying—is capitalism ruining dating? It doesn't have to. This is the way people are meeting. But in person still remains the most important way to figure out if you're attracted to someone. You can't do it online. I think you can get sort of clues. The more clues you can get, the better. That's not bad.

Kara Swisher: All right, next question. Here's a question about the business of dating. It came via email. "I recently took a job with an online dating services company. Since more and more relationships are starting online, this seemed like a good move. However, like any industry, there are many obstacles to progress like inflation, recession, consolidation, or people seeking out more in-person experience as COVID measures end. There's also competition from other entertainment services like streamers and video games that take up plenty of people's waking hours. What do you predict will happen in the next three to five years with the online dating service industry? And was it a good move to enter this space?"

Kara Swisher: Thanks, Jorge. Jorge, I think it's a great business. I don't think it's going away. It's going to consolidate, but it certainly is. I think people love to get out. I mean, you've noticed it lately. Boy, I was in New York. People are all over the place. I was up in Provincetown. I'm going to France next week. People just love being out now. I think they're going to avail themselves to these services for a long, long time.

Scott Galloway: Yeah, I think it's a great business. You're going to see a bit of a post-pandemic dip because people are getting out more. But online dating is going to continue to be a great business. And also the skills you're likely learning. I mean, this is a platform that attempts to connect buyers and sellers. If you have those skills, you can apply that to other platforms. So at the end of the day, you're not in online dating as much as you are in the online marketplace industry. And that is a booming, great industry. So that is a great place to be.

Kara Swisher: Absolutely. We asked a friend to pivot about this, by the way, and here's what she said. Hey, Kara and Scott. It's Julia Naftalin, senior sex and relationships reporter at Insider.com. In the next year or so, I predict dating apps will become less of a fixture for most singles and more of an auxiliary tool. And that's because people are emerging from isolation, and a lot of them are newly single from a relationship or marriage. They're not looking for their next long-term relationship quite yet and want to spend time with people they already know they enjoy, like their friends and families, or they want to get out in the world and have fun and not message on an app. Also, there's been mounting dissatisfaction with dating apps over the past few years, and time spent swiping, messaging, and setting up dates isn't worth the return for a lot of singles. Everyone is on the mainstream apps now, and it leads to a limitless pool and gamification that can feel really unsavory. Singles looking for something committed in long term will use more targeted and decentralized online dating methods so they can be more intentional about it, like apps for niche interests and lifestyles, dating coaches, and matchmakers.

Scott Galloway: Interesting. I would not agree with her. I think these apps are how people—I haven't seen a fall off in people I know that use them using them. I think that it's still fun.

Kara Swisher: I think some people feel depressed after using them. A lot of gay men, when they're using Grindr or all the others. I can't remember all their names.

Scott Galloway: I wouldn't know that. I have absolutely no idea what you're talking about.

Kara Swisher: Listen, Man Sauce, which is your new name. Man Gravy. Man Gravy, whatever. What is the mental block around my... Because I like gravy and I don't like gravy. Anyway, here's the deal. I don't think... I think people rely on these things, even though a lot of times what I hear from a lot of singles is that they get depressed on these things. You know, Louie used it. Casey used it. He was a little like, this sucks. I just don't think people are going to go away from it because they have more options. I do think people should go out, but it's really hard to meet people out. It really is. I have a million people asking me to fix them up. They are all great. And I don't know if I can do it. Like people are very picky and stuff. So I figure they should pick themselves. I feel like these apps, you get to pick yourself rather than helping people.

Scott Galloway: By the way, how do you get a job as a senior sex and relationships reporter? Sounds awesome, right?

Kara Swisher: I know, right? Julia, nice. Well done, Julia. Well, she's right in the sense that there's so much pent up demand to get out.

Scott Galloway: Yeah. And when you're in a social situation in New York, you can just see people are just hungry for interaction, hungry for touch. I think it's going to be a lot of fun to be single and in a city and going out right now. I think there's going to be more fun than long-term relationships developed in the next six to 24 months. I think people just want to get out and live their lives and have a good time. I think it's going to be in New York. I think it's going to be Sodom and Gomorrah for the next 24 months. I think there's so much pent-up fun, craziness, desire.

Kara Swisher: It did look like that from New York the other day. It did look like that.

Scott Galloway: It did or did not?

Kara Swisher: It did. People were really enjoying themselves. Everywhere I go, it's like that. We were at this event in D.C., and then we came out, and the streets were full of people sort of partying. This was a Wednesday night, I guess, last night.

Scott Galloway: Right. So that was interesting. I think you're right. I do think this idea of more niche apps and experiences. Who didn't try to do that? Tinder tried to do that, just a French thing. I think it's a smart way to meet people at different app things of interest. I think that's always fun.

Kara Swisher: Yeah. So I think there'll be more and more of it. I just don't think people are giving up these things. I think they like them. They're used to them. It's part of dating now.

Scott Galloway: Yeah. It's part of it. You can't avoid them.

Kara Swisher: I'm so glad I was not in that. I didn't use those. Many years ago, I'll tell you a very quick dating app story. When they started Tinder, Barry Diller called me and said, oh, you got to try this thing. It was at Hatch Labs, which he was involved with. So I went on and I didn't realize you couldn't be quiet. Like I hadn't done them. And this was a new thing where in most apps you can sort of be quiet in the background. But this one, you were up and running the minute you got on it. And so I immediately started getting matches. And it was so just, I was like, what? What just happened? I couldn't just sit here quietly off to the side and look at it. And it was all older lesbians from Oakland or young goth girls from San Francisco. That was interesting. And then I immediately went off. I was like, ah, and I happened to be married at the time. And I was like, wow, this is crazy. But another friend of mine who's well-known was like, I can't go on them because they're well-known. But one of the things that was interesting was I found them immediately disturbing and riveting at the same time, if that makes sense. I don't know. Have you ever used them? Do you use Raya?

Scott Galloway: I've never been on a dating app. That was just sort of predated me also. And this is going to sound, I don't know, egotistical. I just don't want the little theme I have. I just don't want to be on a dating app. I don't.

Kara Swisher: I figured. I was worried about that.

Scott Galloway: And I'm not being disparaging. I think if you're single, I think it's a great thing. I think people should use it. I see it as multi-channel marketing.

Kara Swisher: Multi-channel romantic.

Scott Galloway: Yeah, but if you're in the mating game. Look, if you're just looking to hook up, great. There's apps for that. And there's nothing wrong with that. If you're looking for a relationship, you want to attack it in a multi-channel manner. You want to talk to your friends, say, set me up. You want to go to events. You want to create random moments of serendipity. And you also want to be on the apps. I don't think there's anything wrong with that.

Kara Swisher: Multi-channel marketing for your man gravy. All right, Scott, let's go on a quick break. When we come back, questions about moving beyond monogamy.

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Kara Swisher: Okay, Scott, we're back. The question comes from Heather via email on a topic we got a lot of questions about, surprisingly. I'll read it. Hi, Kara and Scott. What are your thoughts on monogamy in the 21st century? I've been very happily married for 25 years. My husband and I have talked about inviting another person into our relationship, a man or a woman. We haven't decided on it yet. My own kids in their 20s have a more fluid idea of relationships. Are my husband and I too old to explore outside traditional monogamy? Huh. Well, Scott, you first.

Scott Galloway: Oh, no, you first, Scott.

Kara Swisher: No, well, I think it's fine. I think if that's what you want, as long as you—I do think jealousy still plays a role here and it can be very damaging. I've seen it work with some people. When it's intentional, when it's not intentional, it's always terrible. But I do think that I've seen it work and I've seen it not work, both. It just depends on how people handle it. Obviously, living in San Francisco, you see it a lot, open relationships. They have all kinds of different names and things like that. And there are whole communities of it. I forget the name of the community. Anyway, there's a lot of it. It was in San Francisco. And again, it's interesting, interesting families that people build around it. I think it's harder in practice than it is in concept. It makes a lot of sense. But in practice, I think it's very difficult to do. What do you think?

Scott Galloway: I think you need to ask yourself, you and your husband, and it sounds like you have a very open, positive relationship in terms of communication. I think you have to ask yourself a few questions. One, are you interested in having a threesome or are you basically just one or both of you want to fuck someone else and pretend that it's okay because the other person's there? Fair point. And if you're looking, if one or both of you, and also, is it really, is one person driving this and the other person's just going along to try and please them? But I think we are changing our viewpoint on this. And that is, it used to be mostly kind of dictated by the church that any sex outside of this one relationship is wrong and a sin. And I don't think that's true. And Esther Perel would tell you that affairs, that kind of the French have it, I don't want to say right, but they're not necessarily wrong, that there is a model around extracurricular activity in the context of healthy relationships.

Kara Swisher: Well, gay men do that a lot. That's been the history of a lot of gay men.

Scott Galloway: Well, I think straight people do it a lot. I just think they're less open about it and less in touch with it.

Kara Swisher: That's correct. It's more taboo. And there's—look, I think—I just think you have to break it down. Are we really interested in having a threesome or are we just bored? And are there other ways of satisfying that boredom without necessarily bringing a third person in?

Scott Galloway: I find the idea of a threesome exhausting just physically at my age.

Kara Swisher: Yeah. And also, you just really have to be—

Scott Galloway: I'd go have a sandwich. That's what I would do.

Kara Swisher: There you go. There you go. Also, I do think you have to be honest about the ramifications around what it means to watch your partner fuck someone else in front of you. I don't think you should take that lightly. What will that actually do potentially to the relationship? And two, also, there's a third person involved here. And so I think it's—I've, quite frankly, just find that it's a lot of moving parts.

Scott Galloway: A lot.

Kara Swisher: And I'm about—I do think that we're getting more in touch with what it means. What does monogamy mean? I mean, I think the most wonderful thing about monogamy, and most people define it through the lens of sex with just one person, and I think that's part of it. But monogamy—the most wonderful thing about monogamy is I commit irrationally to your well-being. I'm your partner. If you suffer from mental illness or a financial disaster or you get sick, I am here for you. I think that's what monogamy is. Now, if it also includes not having sex outside of the relationship as a means of demonstrating that commitment, that's wonderful. And I think that is the primary construct that works in most marriages.

Scott Galloway: Yeah, dedication to someone. I think it's interesting you said kids are more fluid and are we too old? I don't think anybody's too old to be thinking of new things. It just really has to be. The ones that have worked have been very rules-based. I'll tell you that. I know that. When it's a little too fluid, it's just as sloppy as what it is. And it always ends badly. I mean, I just, I can think of a dozen people. And then I've seen it work. And I think it's just a point of view. But I do think a clear commitment to one person tends to be, and you have very important—listen, I have a lot of friends who are very important to me. Not absolutely equal to my marriage, but close, right? Or critical, important relationships. Relationships with my kids are just as important in a lot of ways, although people discuss this differently. So, you know, I think you have to think about this, deciding whether you have a man or a woman. That's a big decision.

Kara Swisher: Usually there's another woman in a straight relationship, but who knows on that one. That's an interesting point. But you brought up the reason why threesomes are more common with, especially gay men. Gay men aren't as hung up, don't have the same hang-ups. There are no constraints or filters, or not as many. Women purposely have a finer filter because sex for them has much more downside because of pregnancy. But when there's no filter or there's no constraints, men are like, oh, you seem hot, let's have sex. They just get to it right away. And I don't resent that. And I think gay people probably push back on that and say I'm oversimplifying it. But I find my gay friends have less hang-ups about sex. I'm actually quite a little bit jealous of it. Also, when it comes to a threesome, you're bringing in a third partner. And in a heterosexual relationship, the key question is, are you bringing in another man or another woman? But it's different. It's more complicated with heterosexuals. Here's what we say to you. Go for it, Heather. Go for it. But be thoughtful if you're going to go for it, that kind of thing. But you're not too old. And, you know, if that keeps you of interest, you could also do a lot of other things like travel. You know what I mean? It's just keeping your relationship interesting.

Scott Galloway: Take a cruise.

Kara Swisher: Take a cruise.

Scott Galloway: Don't take a cruise. Because no.

Kara Swisher: Should we do a threesome or should we go to Alaska? Yes, I know. I don't know. I did a threesome 100 years ago when I was young and I literally was so bored. I literally wanted to have a sandwich.

Scott Galloway: Was it with two other women?

Kara Swisher: Yeah.

Scott Galloway: I was bored out of my mind. Was alcohol involved?

Kara Swisher: No, no. I mean, maybe they were drinking. I don't drink as, you know, I'm consistent in that regard, not very much. But I was bored. I was like, okay, I want to go have a sandwich was the thing I thought of the entire time. I'm not that. I'm really not that. I'm so traditional in many ways. But here you have it. I've never had the inkling to want to do this, but others do. I've seen it work. I have not. Anyway.

Scott Galloway: We were pretty much no help there.

Kara Swisher: We were no help. Go for it. Go for it. Be careful. That's what we would say. And don't get someone online. Find someone you know. How about that? Let's not use digital means.

Scott Galloway: I'm not sure that's the way to go with threesomes. I think there's something to bringing in someone you don't know.

Kara Swisher: Oh, really? I think it creates complexity. If it doesn't work out well.

Scott Galloway: Oh, yeah. You don't want to see them at the Whole Foods.

Kara Swisher: I would argue you want a guest star.

Scott Galloway: Yeah, you don't want a guest star. And now bringing in Heather Locklear.

Kara Swisher: All right. Last question. Here, this one's an email. I love Kara and Scott and would totally trust them to set me up with a fun Pivot listener. Where do I sign up? Thank you, Heidi. Heidi, you really have no judgment whatsoever. You should not trust us to set you up at all. So I don't know what to tell you. We're not launching a dating site just yet, but if you're looking for someone who will listen to your favorite podcast with you over some hot cocoa, try using the hashtag PivotSingles. There you go.

Scott Galloway: Oh my God.

Kara Swisher: Yeah. We would like to be, you know what? I have to say of all the people I've met recently, because people have been coming up to me like crazy. I told this to Scott. But there are a lot of them that say they're single. I'm like, oh, I could fix you up with the other person. The air marshal, I think the air marshal had someone with him. But I thought about that. I'm like, I wonder if we could have like get-togethers with fans.

Scott Galloway: No, that's what we're going to have. We're going to have it. I'm very serious about this. Our next PivotCon is going to have a dramatically reduced pricing for people under the age of 35 or 40. And if that's ageist, yeah, you're right, it is. But there was some sexual tension at our last PivotCon. Specifically, everyone came up to me and they're like, is Brian Chesky single? Do you know him? Do you know him? Like, could you set him up with me?

Kara Swisher: I would like to set him up. He's really nice.

Scott Galloway: Well, everyone wants the nice Jewish billionaire. What do you know? People are interested. People are interested in being set up with a 40-year-old, a thoughtful 40-year-old who likes his mother and happens to be worth $10 billion. What a shocker.

Kara Swisher: What a shocker. He's a really nice guy. He's the full package. He'd be good without the billions, let me just say. I'll tell you.

Scott Galloway: I don't know. No, no, I'm telling you. He'd be good without the billions. He'd be very good.

Kara Swisher: OK, fine. He finds a nice Jewish girl. Now he's going to date a fucking supermodel. Just let me word up. The billions makes you very sexy.

Scott Galloway: I don't know. You're wrong. You're wrong. I couldn't be more right on this. You are not. It does. If you're a billionaire, you can also get. But in this case, he could get it on his own. Some of them, I don't know if they would get it on their own.

Kara Swisher: No, I'm not saying you'd be a virgin. I'm just saying. Which billionaire would you date?

Scott Galloway: Which billionaire would I date? If you had to, if you did.

Kara Swisher: Oh, 100%. I'd date Beyoncé. I think she and I would hit it off really well.

Scott Galloway: No, a man. I have to date a man?

Kara Swisher: Yes, yeah.

Scott Galloway: Which billionaire would I date?

Kara Swisher: Yeah, Elon.

Scott Galloway: Elon? He's had seven kids.

Kara Swisher: Yeah, oh, that's true. Oh, wow.

Scott Galloway: I'd like to be in a relationship with Bill Gates, as long as I didn't have to see him naked. Bill, call me. I think he's a thoughtful, nice man. I like Bill Gates.

Kara Swisher: All right. Okay. Well, okay. Then there you have it.

Scott Galloway: Great.

Kara Swisher: It's a dating show where we're setting me up with 60-year-old men. How did we get here? I cannot believe how amazing and lovely your wife is at this point. I really can't.

Scott Galloway: That's because we bring in really hot men to our threesomes. I'm sorry.

Kara Swisher: Go ahead. I love this show so much. Have I said that? Have I said that yet? Those were some great questions. We had a lot of fun. Obviously this may be our last dating questions for a bit. But if you've got questions about business, tech, politics, or anything, we're going to go, we're going, is it vertical? We're going vertical.

Scott Galloway: No, vertical. We're going vertical.

Kara Swisher: Go to nymag.com slash pivot and submit it for the show. And hear more about the dog's horizontal life.

Scott Galloway: Oh, that was good.

Kara Swisher: Oh my gosh. I'm going to stop this before it gets worse. Okay, Scott, that's the show. We'll be back on Friday with a regular episode where we will not be discussing his man gravy or his horizontalness. Scott, please read us out.

Scott Galloway: Today's show was produced by Lara Naiman, Evan Engel, and Taylor Griffin. Thanks also to Drew Burrows, Emil Silverio, Ernie Entretot, engineer on this episode. Make sure you're subscribed to the show on Apple Podcasts, or if you're an Android user, check us out on Spotify or, frankly, wherever you listen to podcasts. Thank you for listening to Pivot from Vox Media. We'll be back next Tuesday for another breakdown of all things tech and business.

Kara Swisher: Call me Esther Dogel, the new maestro of love. God.