Can the “meet-cute” meet tech?

Note: Transcripts are automatically generated from episode audio, and are not fully corrected for spelling, grammar, and formatting.

FRANCESCA HOGI: 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? There are other ways to approach it that don’t rely only on technology.

RANA EL KALIOUBY: I’m not a control freak. I’m not, but I —

JEFF BERMAN: I’m not.

EL KALIOUBY: I’m not. But I like to get organized, have a to-do list, and tackle it one step at a time. I’m learning that love doesn’t quite work that way.

Copy LinkInside Rana’s dating spreadsheet

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 onstage at Summit with Masters of Scale host Jeff Berman and relationship expert Francesca Hogi, and we were talking about my dating journey and my search for a life partner. It felt very bold and courageous to get onstage and talk about this, but it was also very fitting for the theme of Summit. 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?” It kind of went viral on LinkedIn. It sparked a lot of debate and conversation, and I think it was really powerful. Before we get into it, we thought it would be fun to do a quick Q&A and ground the conversation.

To help provide some context, in case you’ve not seen that article, here with me today is our new producer, Alan Montecillo. Hi, Alan. Thanks for being here.

ALAN MONTECILLO: Hey, Rana. Really glad to be here and to help set up this conversation. I agree, it’s a really special episode. I want to start by asking about your own backstory when it comes to relationships and 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?

EL KALIOUBY: 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. 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 a project, and I’m going to crush this project.” I was going to be very systematic about it. I logged every date. I created an algorithm, a weighted algorithm, for all of the different criteria that mattered to me, and I would rate every date based on those algorithms. Then I would also free-form some comments, just to capture how it felt.

MONTECILLO: And all of this data, the weighted algorithms, your thoughts, that all sort of manifested in a spreadsheet, right?

EL KALIOUBY: Correct. I had this spreadsheet, and in the article, there’s a redacted version of it. It’s not all the rows, and there are no names or anything. I have had people I’ve been on dates with reach out to me, and they’re like, “Am I row number four on this sheet?” I’m like, “No comment.”

MONTECILLO: Well, you’ve said that the spreadsheet method really fits your personality, right? Do you find that that’s more common in the tech space, approaching personal journeys and personal issues with this sort of systematic approach?

EL KALIOUBY: I think it’s a very engineering mindset, and I do think this is not uncommon. Actually, when I wrote this article, a lot of people reached out and were like, “Oh my God, your spreadsheet looks like my spreadsheet.” And I was like, “Wow. I guess I’m not alone.”

MONTECILLO: And in terms of the LinkedIn piece, there were, I believe at last count, 138 comments on it.

EL KALIOUBY: Yeah.

MONTECILLO: I’m curious what the response was 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.

EL KALIOUBY: Yeah. What I also did in the article, which again is so outside of my comfort zone, is I basically put out a call. I was like, “Maybe AI will be my matchmaker, but maybe everybody in my existing network could also be helpful here,” right? So I put a call out to the universe, basically, to get some help in this process, and I was completely blown away by the responses. There were also a lot of DMs and private messages. But I think the majority of the responses were just a lot of validation from people for whom modern dating is just not working. There are a lot of people, both men and women, who are struggling to find their partners worldwide. It was just amazing. I heard from people in Greece and Australia and, obviously, the U.S. and Egypt. Then there were a handful of people who also recommended other AI products that could be interesting. I think this idea of AI being a matchmaker is catching on. There are a few startups building in that space. Then there was this debate, right? Some people were like, “You cannot engineer your way into love, full stop. Just surrender, let go, and when the time’s right, your partner will emerge.”

MONTECILLO: Let the universe run its course.

EL KALIOUBY: Exactly. And so for me, the Summit conversation and the Summit theme around “our agency now” sparked this question: 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 this interesting tension between surrendering and also having agency.

MONTECILLO: Well, that’s a great segue. Thank you so much, Rana, for that backstory. Right after this break, you’ll hear Rana onstage with Francesca Hogi and Jeff Berman at Masters of Scale Summit in San Francisco.

[AD BREAK]

BERMAN: This next conversation, we’re calling Love Unoptimized. To lead that discussion, we will ask our very own Dr. Rana El Kaliouby to return to the stage with our friend Francesca Hogi, the founder of True Love Society. Here we go.

EL KALIOUBY: All right.

BERMAN: Hi.

EL KALIOUBY: This’ll be fun.

BERMAN: This is going to be fun.

EL KALIOUBY: Yeah.

Copy LinkWhy dating like a sales funnel fell short

BERMAN: 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.

EL KALIOUBY: Yes.

BERMAN: Where you rated them and said all sorts of things about them. I think we might have an image of it we’re going to bring up. Will you tell us about the spreadsheet, the post, and what happened?

What are we seeing up there?

EL KALIOUBY: Okay.

BERMAN: There we go. Shirt not ironed.

EL KALIOUBY: Shirt not ironed.

BERMAN: No chemistry. Were those related?

EL KALIOUBY: Yeah, yeah. I was like, “Okay, I’m going to take a very systematic engineering approach to this.” It’s like a sales pipeline. I’m like, “I’m going to build the funnel.” And I had a weighted algorithm for each date, and then some commentary, too. Every date got a score from one to five. Five was awesome. It meant, like, “You get a second date.” And yeah, 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. It ended a year ago. Then I was like, “I’m ditching the dating spreadsheet.”

BERMAN: Why? Why ditch it?

EL KALIOUBY: Because I feel it was overengineered, and it didn’t leave any space for serendipity. It was just too 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.

BERMAN: Franchesca, was it overengineered?

HOGI: I mean, look, it kind of worked, right? I think dating is an important process, and I think what was really good about what you did, Rana, is that you did learn a lot about yourself.

EL KALIOUBY: Absolutely.

HOGI: So I certainly wouldn’t recommend that everyone take this approach, but I do think it had a time and a place. 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.

BERMAN: And what is that approach that you’d be more aligned with?

HOGI: It’s not treating dating as a job. It’s understanding that it’s not about an algorithm and metrics. 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 with 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 spreadsheet.

Copy LinkBalancing agency with serendipity in love

BERMAN: Did you decide to just leave it all to chance, or did you find sort of a happy medium?

EL KALIOUBY: Yeah, that was the spirit of the LinkedIn article. Basically, I was saying, first of all, is there a role for AI to be my matchmaker? And I vibe-coded my matchmakers. It’s actually not that bad, so there’s that. And then also the universe, right? People I know and people who know me well, can they also be part of engineering this serendipity? I love the idea of engineering serendipity because I want to have agency.

It’s the theme of the Summit.

BERMAN: Yeah.

EL KALIOUBY: How can you have agency and also let go a little bit? That’s kind of the territory I’m trying to explore.

BERMAN: How does that feel?

EL KALIOUBY: It’s uncomfortable. It’s uncomfortable.

BERMAN: Why is it uncomfortable?

EL KALIOUBY: Because I think I am very… I’m not a control freak, I’m not, but…

BERMAN: “I’m not.”

EL KALIOUBY: I’m not. But I like to believe that I’m empowered and I have agency, and if I plan stuff, get organized, have a to-do list, and tackle it one step at a time, it’ll all work out. I think I’m learning that love doesn’t quite work that way.

HOGI: Yeah.

BERMAN: Francesca, how does love work?

HOGI: Oh, gosh. Well, 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. Dating is one chapter of that journey, but it’s not the whole thing. I think a lot of people treat dating, and I think this is what you ran up against with your spreadsheet, as this thing to get through as quickly as possible.

EL KALIOUBY: Yeah.

HOGI: So many people resent having to date. They’re like, “I don’t want to date. I just want to meet the person. I just want to get into the relationship,” as though that’s the finish line and now the journey is over. It’s like, no, the journey continues. So I really see dating as an important process that teaches us so many skills that we need to be in a relationship. I understand your frustration because we are at a place where romantic agency is very low for so many people. 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,” as though that is the only way to meet someone. I also 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?” There are other ways to approach it where you’re still bringing your intention to it, but you’re not only relying on technology.

Copy LinkHow to date with a meet cute mindset

BERMAN: Well, not to be obtuse, but what are those ways?

HOGI: Yeah.

BERMAN: Because it does sort of feel like there are the apps, which are entirely frictionless, and we should talk about the value of friction, or it’s just, “Let’s leave it up to chance and hope something works.”

HOGI: Yeah.

BERMAN: Where are you finding the middle ground?

HOGI: Well, I think there’s intention. That’s the first step. So 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, if there are other humans, you have no idea who’s there. You have no idea how serendipity might unfold, because you could be sitting next to someone in the audience at Masters of Scale, have a nice conversation, and they might say, “Oh, you live in Chicago? I just heard about this great restaurant in Chicago.” Then two months later, you’re like, “Oh, wait, that’s the restaurant that person told me about.” Maybe you go to that restaurant, and maybe you meet someone there, 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?” am I on my phone all the time? Am I closed off? Am I looking people up and down and being very judgmental and deciding there are only certain people I’m willing to interact with? Those are things that you can work on.

EL KALIOUBY: Can I say I’ve been binge-listening and binge-watching all of Francesca’s stuff, and I love the meet cute mindset? Now when I leave my house, I’m intentional. I’m like, “Meet cute mindset, meet cute mindset.”

BERMAN: 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 was part of the Masters of Scale community who was on the dance floor in Miami, Florida, with her friend Ruby Montoya. 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. 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 where he lives or what he looks like or whatever. You at least have to give it a try.” So several months of work go into this, and then there’s ultimately a dinner with a group of women, and they’re putting into the room what they need. When it gets to her, she puts these five things into the room, and Jenna Rich, who’s a member of this community as well, said, “I’ve got the guy.” And Kara Nortman, another member of our community, was at the dinner, and she said, “I’ve got the guy.” I was the guy. That is now my wife. Katherine will be here tomorrow, so she doesn’t know this is happening, so please embarrass her. I’m so grateful for Ruby giving her that prompt, and for Katherine 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.

HOGI: Yes.

BERMAN: Right?

EL KALIOUBY: Yep. Yeah.

BERMAN: 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.

HOGI: Yes.

BERMAN: What do we learn from that?

HOGI: Well, we learn that your wife was intentional. She showed vulnerability.

EL KALIOUBY: Yes, because now you got married, which is awesome.

HOGI: Right? So there’s vulnerability in that. There’s vulnerability in saying, “Yeah, I actually do want to meet someone.” That’s also a challenge for a lot of people, to even express that, because to claim that feels like, what does that say about me? And what if I don’t meet someone? So that right there is huge. Then she had openness, right? She was willing to say, “Okay, maybe I’ll try this approach of narrowing down the list from 37 to five.” 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.

BERMAN: But I want the marble. I want the backsplash.

HOGI: And it’s got to be the Carrara marble, and it’s got to have this, and 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. A simple example is, 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? And I say, “Okay, well, why?” Because I think it’s always a good question to ask: Why do I want this thing that I want? 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, okay, 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 with whom 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 your now wife showed in being willing to say, “Okay, actually, what is the most important thing here?” I mean, that’s everything. If she had gone and said those 37 things, no one ever would have raised their hand and said, “I’ve got the guy.”

BERMAN: Yeah.

HOGI: Right? We learned that openness is really important.

EL KALIOUBY: Yeah.

Copy LinkShrinking the checklist to what matters most

BERMAN: I just want to acknowledge that there’s a trope, and it’s a trope for a reason. I think it’s particularly true in the Bay, though I’m sure it’s true elsewhere, that there are strong, smart, powerful, beautiful, incredible women

HOGI: Yeah.

BERMAN: who are either partnered with men where it may not just be about the education level, but honestly, we all know it, right? We meet people and you’re like, “Well, she’s great, but he’s…” In all sincerity, there is, to put it in sort of unemotional terms, a market problem here.

HOGI: Yeah.

BERMAN: Right?

HOGI: Yeah.

BERMAN: Let’s just call it out and say the thing, right?

EL KALIOUBY: No, it’s true.

BERMAN: That’s why we’re here. We’re here to have the real conversation.

EL KALIOUBY: Yeah.

BERMAN: So, Rana, when you hear this and acknowledge that, on the one hand, you’d like the same education level, et cetera, how do you figure out where to compromise?

EL KALIOUBY: Actually, you and I had a conversation a few years ago, and I whittled it down to five. So you inspired that.

BERMAN: Well, that’s Kathryn, but thank you.

EL KALIOUBY: That, and Kathryn, yeah.

BERMAN: Yeah.

EL KALIOUBY: For me, it’s generosity of spirit. I think that’s really important. The five reflect my own core values: growth-minded, having a gratitude mindset, being generous, and also being gorgeous. I think that’s important. Being intentional and having that clarity is helpful. And then having the courage to put it out there, which is definitely not easy.

BERMAN: How do you muster that courage?

EL KALIOUBY: I mean, I’m here.

HOGI: Yeah.

BERMAN: Yeah.

HOGI: I am so proud of you, by the way.

BERMAN: Yeah, by the way.

EL KALIOUBY: I also think for a very long time, I felt very lucky, privileged, and blessed. I have amazing kids, my parents are alive and around, amazing friends and community, and I love what I do. So 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. For the longest time, I actually felt guilty verbalizing that, and I felt like I would be judged.

And now I’m kind of trying to embrace that 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 a month, and then one day I was like, “Okay, click go.”

Copy LinkWhy vulnerability creates more connection than polish

BERMAN: Why did you sit on it for a month, and what gave you the courage to hit send?

EL KALIOUBY: Because I felt like there would be a lot of judgment.

Also, even putting it on LinkedIn, which is a professional network, or a network for professional connections, there was a question of whether this would even be the right forum to bring this up. 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. I also wanted it to be authentic and vulnerable. I didn’t want it to be flowery, so I tried to really 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.

BERMAN: Any good setups or DMs?

EL KALIOUBY: A few people were very thoughtful, and they reached out and were like, “Oh, I saw your LinkedIn. I think I’m the guy.” But in a very thoughtful way.

BERMAN: Yeah.

EL KALIOUBY: It was all very thoughtful.

BERMAN: Yeah. Not too thirsty.

EL KALIOUBY: Yeah, no, it was all very thoughtful. And then some people offered to connect me to other people. It was great. But honestly, that wasn’t even it. I feel like it was a win just by putting it out there.

Copy LinkTrading scorecards for intuition and reflection

BERMAN: Yeah. What’s replaced the spreadsheet now? How are you approaching this in this next phase?

EL KALIOUBY: I am not tracking in a spreadsheet. I do journal a lot, so my thing that I’m trying to do, the journey I’m on again, is this: my book was called Girl Decoded, and it was very much about engineering, artificial emotional intelligence. My next book, if I write one, would be Girl Embodied.

HOGI: Ooh.

EL KALIOUBY: How can I trust my intuition and really connect with how I truly feel? Because I do feel that in this age of AI and the noise, it’s really hard to listen to your inner wisdom.

BERMAN: Yeah. Will you share the journaling project you’re undertaking right now?

EL KALIOUBY: Yeah, okay. There’s this book called The Book of Alchemy, which I love.

HOGI: Yes.

EL KALIOUBY: 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. It’s been quite healing and very insightful.

Copy LinkSetting clear intentions and putting them out there

BERMAN: Good. OK. Francesca, I’d like to close by asking you this as we head into this evening.

HOGI: Yes.

BERMAN: There are people in this room who are looking for something. It could be love, it could be a coach —

EL KALIOUBY: A co-founder.

BERMAN: It could be a thought partner, a co-founder. It could be a micro-community to support something. Any number of things.

HOGI: Yeah.

BERMAN: 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?

HOGI: Well, I think if everyone would just take a minute or two to set that intention: What kind of connection would you love to make here at Summit? That’s the intention part. Then, to practice the vulnerability part, I would also encourage you to share that with someone. Sometimes with these things, you don’t know what to say to strangers you haven’t met yet. 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”? You never know what kind of serendipity might evolve from that.

BERMAN: Yeah.

EL KALIOUBY: Yeah.

BERMAN: 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, and that you were willing to come onstage and have this conversation. I think it’s going to help a lot of people here.

EL KALIOUBY: Meet-cute mindset.

HOGI: Yes.

BERMAN: Meet-cute mindset.

EL KALIOUBY: Mindset.

BERMAN: Let’s go.

HOGI: It’s a way of life.

BERMAN: Thank you, guys.

HOGI: Also, learn how to flirt.

BERMAN: Thank you.

EL KALIOUBY: Oh yeah, absolutely.

HOGI: Thank you.