愛を最適化しない：「ミート・キュート」はテクノロジーと出会えるか

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I'm Bob Safian, former editor-in-chief of Fast Company, and I'll be your host as each episode breaks down what you need to know right now. You can find Rapid Response wherever you get your podcasts. I want to meet someone, but I don't want to be on a dating app. Well, if I'm not on an app, then what am I doing? And there are other ways to approach it that you're not only relying on technology. I am a very, I'm not a control freak. I'm not. I'm not. But I like to get organized and have a to-do list and tackle it one step at a time. I'm learning that love doesn't quite work that way. Hi, everyone. It's Rana here. This week, we are bringing you another conversation from the Masters of Scale Summit stage in San Francisco.

And this episode is a very special one. I was on stage at Summit with Masters of Scale host Jeff Berman and relationship expert Francesca Hoagie. And basically we were talking about my dating journey and my search for a life partner. It sounds very bold and courageous to get on stage and talk about this, but it was also very fitting for the theme of Summit. But the theme this year is our agency now. And we all felt it would be really powerful to apply that discussion to perhaps the most important part of our lives, which is our human connections and our human relationships. This was all inspired by a LinkedIn article that I wrote titled, I Retired My Dating Spreadsheet, Can AI Help Me Find Love? And it kind of went viral on LinkedIn. It sparked a lot of debate and a lot of conversation. But I think it was really powerful. Before we get into it, we thought it would be fun to do a quick Q&A and just kind of ground the conversation. And so to help kind of provide some of this context in case you've not seen that article, here with me today is our new producer, Alan Montesilio.

Hi, Alan. Thanks for being here. Hey, Rana. Really glad to be here and to help set up this conversation. I agree it's a really special episode. So I want to start by asking about your own backstory when it comes to relationships and also your approach to dating in years past. You were on the apps, as they say, as a working mom, and it was a new world to you. So what was your strategy at the time? Yeah, I've been divorced for about a decade. I moved to the U.S. basically to Boston with my two kids at the time. They were 10 and 4, and I was busy running the company. So I didn't start dating until 2019. I got on a few of the apps and I approached it pretty much like I'd approach anything else in my life. I'm like, this is like a project and I'm going to crush this project. And I'm just going to be very systematic about it. And I loved every date. I created kind of an algorithm. It was like a weighted algorithm. So all the different criteria that mattered to me and I would rate every date kind of based on these algorithms.

and then I would kind of also freeform some comments, right, just to kind of capture how it felt. And all of this data, the weighted algorithms, your thoughts, that all sort of manifested in a spreadsheet, right? Correct. I had this spreadsheet, and in the article there's a redacted version of it. It's not all the rows, and there's no names or anything. I have had kind of people I've been on dates with reach out to me, and they're like, am I row number four on this? And I'm like, ah, no comment. Well, and you said that that spreadsheet method, that it really fits your personality, right? Do you find that that's more common in the tech space, kind of approaching personal journeys, personal issues with this sort of systematic approach? I think it's very, like, it's a very engineering mindset. And I do think this is not uncommon. Or actually, I found out when I wrote this article, a lot of people reached out and they were like, oh, my God, your spreadsheet looks like my spreadsheet. And I was like, wow, I guess I'm not alone. And in terms of the LinkedIn piece, there were, I believe at last count, 138 comments on it.

Yeah. I'm curious what the response is like for you and if there's anything that stands out to you in particular from what people were saying in response to the piece. Yeah. What I also did in the article, which, again, is so outside of my comfort zone, is I basically put a call out. I was like, maybe AI will be my matchmaker, but maybe everybody in my existing network can also be helpful here, right? And so I put a call out to the universe, basically, to, you know, to get some help in this process. And I was just completely blown away by the responses. There's also a lot of, like, DMs, private messages. But I think the majority of the responses was just a lot of, like, validation. People who either like modern dating is just not working for them. And, yeah, there's a lot of people, both men and women, who are struggling to find their partners worldwide. It was just amazing. I heard from people from Greece and Australia and obviously the U.S. and Egypt.

And then there was a handful of people who also like recommended other AI products that could be interesting. I think this idea of AI being a matchmaker, there's a few startups that are building in that space. Oh and then there was like this debate right Some people were like you cannot engineer your way into love full stop Just girl like just surrender let go And when the time right your partner will emerge Let the universe run its course. Yeah, exactly. And so for me, the summit conversation and the summit theme around, okay, our agency now like sparked this question of, I want to have agency, but I don't want it to be forceful agency. I want it to be serendipitous. So I don't know. It's like kind of this interesting tension between surrendering but also having agency. Well, that's a great segue. Thank you so much, Rana, for that backstory. Right after this break,

you'll hear Rana on stage with Francesca Hoagie and Jeff Berman at Masters of Scales Summit in San Francisco. This next conversation we're calling Love Unoptimized. And to engage that discussion, we will ask our very own Dr. Rana El-Khalubi to return to the stage with our friend Francesca Hoagie, the founder of True Love Society. Thank you. This is going to be fun. Rana, it is not easy to go viral on LinkedIn.

You managed to do it when you published a post talking about a spreadsheet that you built tracking your dates where you rated them and said all sorts of things about them. I think we might have an interview that we're going to bring up. Will you tell us about the spreadsheet and about the post and what happened? What are we seeing up there? There we go. Shirt, not iron. No chemistry. Are those related? Yeah, clearly. Exactly. Like, I was like, okay, I'm going to, like, take a very systematic engineering approach to this. It's like a sales pipeline. I'm just, like, going to build the funnel. And I had a weighted algorithm for each date and then some commentary, too. And so every date got a score from one to five. Five was awesome. It went, like, you got a second date. And, yeah. And then I did that for a number of years, ended up in a three-year relationship, which was both the best thing ever and the worst thing ever. ended a year ago and then I was like I'm ditching the dating spreadsheet why why ditch it because I

feel it was over engineered and it didn't feel it didn't leave any space for serendipity um yeah it was just like over mechanical and my new frame of mind is that maybe I just need to surrender and let go a little bit more which is very hard for me but that's the journey I'm on um Francesca was it over engineered I mean look it kind of worked right I mean I think you know Dating is an important process, and I think what was really good about what you did, Ronna, is that you did learn a lot about yourself. Absolutely. And so, I mean, I certainly wouldn't recommend that everyone take this approach, but I do think that it had a time and it had a place, and I also understand why now you're ready for a different approach, which is an approach that I would be more aligned with. So, yeah. What is that approach that you'd be more aligned with? So it's not teaching – it's not treating dating as a job. is understanding that it's not about an algorithm and metrics and that there is, I mean, love is a spiritual thing, right? It's not physical. It's not something you can hold in your hands or put in your pockets,

but it's something that is very real. And it's something that you have to surrender to some serendipity. You have to understand the power of your own intuition in the process of finding love. And, yeah, that's not something that can be engineered via spreadsheets. Did you decide to just leave it all to chance? or did you find sort of a happy medium? Yeah, that was the spirit of the LinkedIn article. Basically, I was saying, well, first of all, is there a role for AI to be my matchmaker? And I vibe code to my matchmaker. It's actually not that bad, so there's that. And then also, like, the universe, right? Like, people I know and people who, you know, who know me well, can they also be kind of part of engineering the serendipity? Like, I love the idea of engineering serendipity because I want to have agency. is the theme of the summit. How can you have agency and also let go a little bit? And that's kind of... I'm trying to explore that territory. How does that feel? It's uncomfortable. It's uncomfortable.

Why is it uncomfortable? Because I think I am a very... I'm not a control freak. I'm not. I'm not. I'm not. but I like to you know I like to believe that I'm empowered and I have agency and if I kind of plan stuff and like you know get organized and have a to-do list and just like kind of tackle it one step at a time it'll all work out and I think I'm learning that love doesn't quite work that way yeah um Francesca how does love work oh gosh well I you know I really see love as something that we are here to get better at. We're here to grow more skilled at giving love and receiving love. And I think that is a lifelong journey. And dating is one chapter of that journey, but it's not, it's, it's not, um, it's, I think a lot of people treat dating. And I think this is kind of what you ran up against with your spreadsheet as this thing to get through as

quickly as possible, right? Like so many people resent having to date. Um, they're like, I don't want to date. I just want to meet the person. I just want to get into the relationship. And as that's, as though that's the finish line. And now the journey is over and it's like, oh no, no, the journey continues. So I really see, I really see dating as an important process that teaches us so many skills that we need to be in a relationship. Um, and so I, I really see, and I understand your frustration because we are at a place where romantic agency is very low for so many people. You know, one thing that I hear from people all the time is, well, I want to meet someone, but I don't want to be on a dating app. And, you know, as if though that is the only way to meet someone. And so I also just want to be clear that for me, when I say serendipity, I'm not saying don't be intentional, right? Because I think a lot of people feel like, well, if I'm not on an app then what am I doing And there are other ways to approach it that you still bringing your intention to it but you not you know only relying on technology Well not to be obtuse but what are those ways right Because it does sort of feel like there is you know the apps that are entirely frictionless

and we should talk about the value of friction or just like, let's leave it up to chance and hope something works. Where are you finding the middle ground? Yeah, well, I think there's intention. That's the first step. So, you know, I have this concept that I teach called the meet cute mindset, which is really the belief that every time you leave your house, you have the potential to meet someone special wherever you are. And there are other humans. You have no idea who's there. You have no idea how a serendipity might unfold because you could be sitting some next to someone in the audience at Masters of Scale, have a nice conversation. They might say, oh, you live in Chicago. Oh, I just heard about this great restaurant in Chicago. And then, you know, two months later, you're like, oh, wait, that's that restaurant that that person told me about. And maybe you go to that restaurant and maybe you meet someone at that restaurant right because serendipity is not always a linear thing it's a winding kind of road so if you move through the world with that openness of okay well how am i showing up right am i on my phone all the time am i closed off am i looking people up and down and being very judgmental and only deciding there's certain

people that i'm willing to interact with then those are things that you can work on right so Can I say, I've been binge listening and binge watching all of my stuff and I love the meet cute mindset. And now I like, when I leave my house, I'm like intentional. I'm like, meet cute mindset, meet cute mindset. Well, I want to share a quick story that maybe helps optimize a little bit for this. So about four years ago, there was a woman who's part of the Masters of Scale community who was on the dance floor in Miami, Florida with her friend Ruby Pantoya. And Ruby said, you're amazing. Why are you single? And she said, well, here's what I'm looking for. And it was like 37 items on the list. And Ruby said, no, no, no, you have to get down to five. You have to get down to five. And if you're set up with someone who meets all five, you have to go on the date no matter, you know, where he lives or what he looks like or whatever, which, you know, maybe. But whatever. You at least have to give it a try. And so, you know, several months of work goes into this. And then there's ultimately a dinner group of women. And they're putting into the room what they need.

And when it gets to her, she puts these five things in the room. And Jana Rich, who's a member of this community as well, said, I've got the guy. And Karen Nortman, another member of the community, was at the dinner, and she said, I've got the guy. I was the guy. That is now my wife. Catherine will be here tomorrow, so she doesn't know this is happening, so please embarrass her. But, you know, and I'm so grateful for Ruby giving her that prompt and for Catherine taking it and putting it out there and taking the date despite geographic challenges and what have you. It does feel like she sort of engineered the serendipity. Yes. Right? Yep. Yeah. What do we, talk about me. What do we take from that story that helps not only for dating, but, I mean, look, we're going to wrap today. We're going to go to a great party. You want to optimize for the right meet-cute for whatever you're looking for. What do we learn from that? Well, we learned that your wife was intentional.

You know, she showed vulnerability. Just because now you got married. Like, this is awesome. Right? So there is vulnerability in that. There's vulnerability in saying, yeah, I actually do want to meet someone. And that's also a challenge for a lot of people, just to even express that. Because to claim that feels like, but, you know, what does that say about me? And what if I don't meet someone? And then, you know, so that right there is huge. And then she had openness, right? She was willing to say, OK, maybe I'll try this approach of narrowing down the list from 37 to 5. And as a former matchmaker, I can tell you this is a conversation you have to have with a lot of people. It's like we're not building a custom kitchen. It's a human. But I want the marble. And it's got to be, you know, the Carrera marble. And it's got to have this. Yeah. So it's important to be willing to be flexible to evaluate because we have all these assumptions about what's going to make us happy. We use so many traits as a proxy for other things. So like a simple example is if you say like I work primarily with professional women.

And so I often hear things like, oh, well, I want someone who has at least the same level of education as I do. Right. I say, OK, well, why? Because it's you know, I just think it's always a good question to ask. Why do I want this thing that I want? And often I'll hear, well, that way he won't be intimidated by me. That way he'll be my intellectual peer. And it's like, OK, well, there are plenty of people who have the same level of education as you or higher who will still be intimidated by you and who you will not have a good intellectual connection. Right. So if that's what you want, focus on that rather than a trait. So the openness that you're now white was shown and showed in being willing to say, OK, actually, what is the most important thing here? I mean, that's she had gone and said these 37 things, you know, no one ever would have raised their hand and said, I got the guy. Right. So, yeah. So we learned we learned that that openness is really important. I just want to acknowledge that there is a it's a trope and a trope for a reason that there are. And I think it's particularly true in the Bay, church through elsewhere, that there are strong, smart, powerful, beautiful, incredible women who are either partnered with men who it may not just be about the education level, but honestly, like we all know it.

Right. We meet people and you're like, well, she's great, but he's my man. Right. I mean, in all sincerity. Right. I mean, there is to put it in really like sort of on emotional terms, there's a market problem here. Right. Yeah. And so, like, I mean, let's just call it out and say the thing, right? I mean, that's what we're here. We're here to have the real conversation. So, I mean, Rhonda, when you hear this and you acknowledge that, like, on the one hand, like, I hear you. Yes, I'd like the same education, et cetera. Like, how do you figure out where to compromise? So, actually, you and I had a conversation a few years ago, and I whittled it down to five. So you inspired that. Well, that's capital. And for me, it's generosity of spirit. I think that's really important. It's one of my core. It's interesting. The five are like they reflect my own core values. So growth minded, you know, having a gratitude mindset, being generous, also being gorgeous. I think that's important.

But I think being intentional and having that clarity is helpful. Yeah. And then and then. Yeah. and then having the courage to put it out there, which is definitely not easy How do you muster that courage I mean I here I am so proud of you by the way Yeah by the way I also think for a very long time, I'm very lucky, and I feel very privileged and blessed. I have amazing kids. My parents are alive and around, like amazing friends and community. I love what I do. I feel very blessed. And I also would love to find a life partner. I think it would be awesome if it's the right life partner. And for the longest time, I felt actually guilty verbalizing that, and I felt like I would be judged. And now I'm kind of trying to embrace, no, it's an okay ask, and it's okay to ask people in my community and put it out there.

So, yeah, I mean, I sat on this LinkedIn article for probably like, yeah, a month. And then one day I'm like, okay, click, go. Why did you sit on it for a month and what gave you the courage to hit send? Because I felt like, well, I felt like there would be a lot of judgment. Also, even putting it on LinkedIn, which is, you know, it's a professional network or a network for professional kind of connections, right? There was a question whether this would be even the right forum to bring this up. And I've always led with being my authentic self. I bring my whole self to work and what I do, and I felt like that is an important part of who I am. And so, you know, I also wanted it to be authentic and vulnerable. I didn't want it to be flowery, so I try to really kind of put myself out there. Every time I do that, though, it just pays off. So many people reached out and connected. So many people resonated with what I said.

Any good setups or DMs? You know, a few people were very thoughtful, and they reached out, and they were like, oh, I saw your LinkedIn. I think I'm the guy. But in a very thoughtful way. It was all very thoughtful. Yeah, not too thirsty. Yeah, it was all very thoughtful. And then, you know, some people offered to connect me to other people. it was great it's great but honestly that wasn't even i feel like it was a win um just by putting it out there yeah what's replaced the the spreadsheet now like how are you how are you tracking how are you approaching this in this next phase i am not tracking in the spreadsheet um i do journal a lot so i try to like my my thing that i'm trying i'm trying to like the journey again i'm on is um my book was called girl decoded and it was very much about like engineering, artificial emotional intelligence. And my next book, if I write one, would be Girl Embodied. Like, how can I trust my intuition and really kind of connect with how I truly feel? Because I do feel in this age of AI and the noise, it's really hard to listen to your inner wisdom.

Yeah. Will you share the journaling project you're undertaking right now? Yeah. Oh, yeah. Okay, yes. There's this book called The Book of Alchemy, which I love. Yeah. and basically you commit to doing one creative project for 100 days and my project is to pick one word a day. Sometimes I just ask people to give me a word and I journal for about five minutes and it's been quite healing and very insightful. Yeah. Good. Okay. Francesca, I'd like to close by asking you this. As we head into this evening, There are people in this room who are looking for something. It could be love. It could be a coach. It could be a thought partner, a co-founder. It could be a micro-community to support on something, any number of things. Without the benefit of weeks or months to think about the five things, what's the mindset, what's the thought exercise that our community should go through between here and the party tonight to optimize for success?

Well, I think if everyone just would take a minute or two to just think about, is that that intention? Like who, what kind of connection would you love to make here at Summit? And that's the intention part. And then to practice the vulnerability part, I would also encourage you to share that with someone. Maybe to share that, I mean, you know, sometimes with these things you don't know what to say to people, like to strangers that you haven't met yet. And wouldn't it be great tonight if everyone was open and willing enough to say, yeah, this is an intention that I have for connection. And you never know what kind of serendipity might evolve from that. Yeah, and I think there's such power in putting it into the room because you just don't know whether it's LinkedIn or a physical event, what will come from it. I am so grateful that you did this, that you shared it, that you're willing to come on stage and share this and have this conversation. I think it's going to help a lot of people here. Meet your mindset. Meet your mindset. It's a way of life. and also learn how to flirt thank you

I left the summit stage feeling so inspired and so seen my big takeaway is the meet cute mindset I love that mindset and I've been trying to adopt it in my daily life so every time I leave the house I try to not be on my phone all the time and just be looking up and smiling to people and maybe just giving compliments. As for the role of AI, I really still do think there is a role for AI in helping kind of engineer serendipity. And so I'm still kind of iterating on my AI matchmaker. But if anybody out there is building something really interesting, I would love to hear from you. And perhaps I can be your guinea pig. So if you are listening to this conversation or watching, please reach out and let me know your thoughts. I love to hear from you. Thank you so much for tuning in. I'll be back next week with a new episode.

Mastering by Ryan Pugh. Original music by Ryan Holiday. You can join the conversation on LinkedIn, Instagram, TikTok, YouTube, and X. Just search for Act Pioneers of AI.