How To Protect Heart, Soul And Self In Online Dating: An Interview With Charly Lester [EP112]

What can we do to protect ourselves from the physical and emotional risks in online dating? And what are the keys to handling the stress, anxiety, and burnout online dating can create? In this interview with brilliant online dating innovator, fearless adventurer and humanitarian Charly Lester, we’ll explore how you can better protect and care for yourself in your online dating life.

Table of Contents

How To Protect Heart, Soul And Self In Online Dating: An Interview With Charly Lester

How To Practice Self-Care And Self-Protection In The World Of Online Dating

What can you do to protect yourself from the physical and emotional risks in online dating, and what are the keys to handling the stress and the anxiety and the burnout online dating can create? In this interview with brilliant online dating innovator and humanitarian Charly Lester, we’re going to explore how you can better protect and care for yourself in your online dating life, so stay tuned to this episode of the Deeper Dating Podcast.

Hello, everybody, and welcome to the Deeper Dating Podcast. I’m Ken Page and I’m a psychotherapist. I’m the author of the book Deeper Dating and the Cofounder of, a site where single people can meet in an online environment that is fun, inspiring, kind and respectful. In this podcast, I am so excited to be interviewing Charly Lester. Let me tell you a little bit about Charly. She is one of the world’s leading dating industry experts. She’s a serial entrepreneur and she currently runs a successful marketing consultancy business for dating apps and tech startups.

She launched her first business at age 30, which was The Dating Awards. Most famously, she cofounded Lumen, which is the dating app for over 50s, which has been the fastest-growing dating app in the world in 2019, and she was profiled in Forbes in 2018 and she is currently preparing to launch her fifth business, Peaches & Poppies, which is a plus-size activewear brand inspired by her own struggles to find triathlon-specific clothing which accommodates her curves. I adore this.

Charly is the former dating editor for The Guardian and the global head of dating for Time Out. She’s been on BBC News Night representing the online dating industry. In 2015, she was an expert advisor to Lord Sugar in the final of The Apprentice, and she’s a regular guest on Radio 4 Woman’s Hour. She’s also an ambassador for the charity Survivors Manchester, which supports male survivors of rape and sexual assault. She cycled from Land’s End to John O’Groats in 2016 and completed her first Ironman in 2018 in aid of this charity.

In her spare time, she enjoys Ironman Triathlons and played for team Romania in the Roller Derby World Cup, and recently completed the Marathon des Sables, six marathons in five days across the Sahara Desert. She is the dating industry expert for RealMe, which is a company that has developed solutions to make dating apps safer. There are just worlds of things that we’re going to be talking about together, but one of the biggest and most central ones is how people can keep themselves safe emotionally, physically, and spiritually in their online dating experience.

If you want to know more about Deeper Dating, and I’ll be telling you all the different ways that you can connect with Charly and her work, and giving you all the links in the transcript. If you want to know more about the Deeper Dating path to real intimacy, just go to and you’ll get free gifts. You’ll learn a lot more about the ideas we speak about, and you’ll get a complete transcript of every episode including this one.

I also just want to say that everything I share on this podcast is educational in nature. It’s not medical or psychiatric advice or treatment. Finally, if you like what you’re learning here, if you like what Charly has to say, if you have any questions, it would just be a tremendous thank you if you subscribed, left me a review or just went to the Ask Me section of, and share any thoughts, feedback or questions about what you hear in this episode. Thank you so much and we are going to jump in right now.

Charly, it’s so great to have you here.

Thank you for having me.

I originally just was so impressed by the quality of your dating advice, which is non-gimmicky and heartfelt and practical, and the combination of the kind of humanitarian aspect of your work that kind of just so integrates in, as well as your sense of adventure. All of the things that are wonderful and kind of part of the dating experience.

I would just like to start out by having you talk about this current passion of yours, which is the issue, well, current and ongoing, but this passion for creating safety; physical, emotional and spiritual, for people who are doing online dating. I just love to hear any of your thoughts and reflections, and what this means to you.

I think I’m probably part of the new wave of dating entrepreneurs in a way because I’ve come at this industry at an age where I was dating still, so if you look at the first people who created online dating sites, a lot of them had been married for like 10, 15 years before online dating came around, and so they never really experienced their products. I think that’s where, you know, I’m in my late 30s and a lot of my sort of fellow entrepreneurs that is in their age, we dated on Tinder, right? We were there the first year that it launched.

I worked at Gaydar for a time, and all of my colleagues, they were all on Gaydar. I think it makes a real difference when you’re actually dating on these products because suddenly you understand the world in a different way. My entry point into the dating industry was I wrote a blog. I went on 30 blind dates before I turned 30.

Sometimes, we give ourselves different advice from the advice that we would give other people.CLICK TO TWEETAs a result of that blog, I was constantly being asked questions by people all around the world about dating, and so I think because I came into this kind of an inverted commerce dating expert role as the dater, and just my expertise comes from having been on thousands of dates rather than an academic qualification or anything like that.

I think it does mean that my advice is often more practical and more kind of in the trenches, and I have seen the experience, yes, I’m a straight female in my late 30s, a straight white female in my 30s, but I’ve seen the experiences of so many different people in this dating space because of writing the blog and speaking to so many people. I worked for Gaydar, which is a men’s, a gay dating app but I also worked, you know, obviously at Lumen, which is for over 50s.

I’ve worked with demographics that I don’t belong to, which I think is really important because actually the best thing you can do, I believe as a founder of a product for the people, is listen to your users. With Lumen, I had a profile in-app where literally, people could message me any time of day and it said, “I’m the cofounder of Lumen.” It went straight to my phone. It wasn’t my community operations team pretending to be me.

It was literally me answering questions at 11:00 at night on my phone to someone who said, “Hey, can you help me improve my dating profile? I’ve just messaged this guy and he’s not messaging me back. What would you recommend?” I think when you start talking to people and you start recognizing the problems that people face time and again, and I’m sure we’ll talk about Lumen in more detail later, but the whole reason I launched Lumen was because that was the question for like four years that I kept being asked, “My mom’s just got divorced. Which dating apps should she use?”

I never had an answer. For me, a good skill in an entrepreneur is if you keep seeing the same problem in multiple places, and you can come up with a solution for it, that’s a suggestion that maybe that solution is needed. That definitely, within the dating space, I’ve seen it time and time again where something is being asked for and no one is catering for it.

Dating And Safety

I deeply agree with that and that was kind of how I began in this entire journey. I was a single gay man who adopted a child and I had no time, and I thought, “What would be the most healing and effective way for me to meet people?” Also, I was an incredibly unskilled dater and I really had to be a student of what I was doing wrong to begin to change that, so I love that.

I love that in the trenches kind of approach and caring about kind of the pain that you saw, and the missing pieces that you saw again and again. I would like to hear from you kind of just around this issue of safety; physical safety and emotional safety. Kind of, what are the things that stand out for you in the over 50 community, in any community at all? What are the key things that stand out for you?

I think in terms of practical safety, I think the key thing, always, is to remember that you’re talking to strangers, and that applies even up on your third date, right? This is a third date. You’ve probably spent 4 or 5 hours in that person’s company. I always liken it to a fellow traveler on a train journey. I mean, you wouldn’t give that person your wallet and your address and your car keys, right? You hear these stories of people’s cars being stolen on a second date. I was like, “It’s because you handed your car keys to a stranger.”

The reality is because we let our heart take over from our head. I think from a practical safety perspective, it’s remembering in those early stages, to try to listen to your head and to almost be like your brutal best friend. When you’re rushing ahead with things, think about it from the perspective of if your friend was telling you this story, what advice would you give him or her? I think sometimes we give ourselves different advice to the advice that we would give other people. I think that that’s really important.

I think from an emotional perspective, I think the problem and I say this is someone who’s worked for multiple dating apps. I think one of the problems of dating apps, a by-product of dating apps is that people have become products, right? We can see people in the same way that we can view apartments, right, on an app on our phone. If I’m online shopping or if I’m looking for an apartment, then I click a load of things that I want and I can specify exactly what I want, right? “I need three bedrooms. I need a garage for my car.”

Well, real life isn’t like that and people are not products, but the way that we see dating apps and the filters we see on dating apps, we start to dehumanize people. I think that that’s the problem with online dating, is to step away. We forget there are people in our pocket. We just see these cards that are the faces and the ages and the names, and we suddenly start forgetting there’s a real human being on the other side.

I can remember really early on when I was writing my blog. I matched with a guy in the early days of Tinder, and we never went on the date, and part of it was from the way that he behaved with me. I met him six months later and he was a really lovely guy and I actually called him up on it. I said, “You are so nice. Why were you like this?” He admitted it himself. He said, “I know. I was chatting so many women. I forgot you were a real person and I just didn’t treat you how I would.”

He was such a good friend, honestly, and I think that what’s quite startling is people behave completely differently to how they would in real life, and so you’re only seeing this one side of their personality. The gamification, the way that the app is designed to be a bit like a game to keep us on there, well it brings out that side of that person, and it’s not their whole self but it’s just what we see of them. I think the key is partly to remember there is a game aspect to this, that this is not total real life. It’s a great way to introduce you to people but it’s not the be-all and end-all.

DDP 112 Charly Lester | Online Dating
Online Dating: When you start talking to people and recognizing the problems they face, you start to craft solutions that could eliminate those problems.


It can get really consuming in the same way that our cellphones are really consuming, right? These days, we spend so much time on our phones that a lot of people I hear are saying, “Oh, this feels like a second job that I’m having to spend hours on.” If you are feeling like this is not fun, if this is feeling like a second job, if you can’t bring yourself to go on and reply to people, then just take a break. We shouldn’t have to, you know, and I would say this to someone who’s been single now for about two years. You shouldn’t have to spend all your time on dating apps.

It is one of those things I think you should do in bursts, and you do it when you’re enjoying it, and then when you’re not enjoying it, you step away from it and do something else because otherwise, you’re not bringing your full best you to the table anyway. I can remember when I first started in the dating blog and I was going on three dates a week for this blog. I remember turning up on a date. I had wet hair because I’d just gone for a swim. I didn’t have any makeup on and I just didn’t care, right?

Being Your True Self

I looked at myself and I actually, because on these dates, I would evaluate the date. Not the guy, but I would give the date that we went on marks out of ten, and on that write up I gave myself 2 out of 10 because I knew that I hadn’t brought my A-game to that date, and it wasn’t fair on the other person. I think that, you know, if you are feeling like your mental health is starting to get a bit sapped or just feeling a bit drained by it all, then take a step away because for me, I think the whole point of dating and the whole point of finding someone is by being your true self, right?

I always say this, my advice when it comes to dating profiles is, “Don’t use filters. Don’t lie about anything because you’re not going to attract the right person, but you still need to be your proper self to attract the right person too. If you’re a rundown, knackered is a very English term, tired version of yourself.

If you’re a rundown knackered version of yourself, then you’re not actually going to attract the right people for you. Because you’re going to attract people who maybe feed off that energy, and actually it could be quite disruptive to go at it when you’re feeling 25% or 50% because I feel like the type of people you’re going to attract is going to be a completely different type of person.

I think that being quite self-aware, I think could be quite important in this and not just feeling like, “Oh, my God. I’ve been single for so long. I have to carry on at this even if I’m not enjoying it because when it comes down to it, this is your life, right? This is a part of your life and it should be enjoyable. You are spending time that you could be spending seeing your friends, doing other stuff, going on these dates. If you’re not enjoying it, just take some time out.

That’s really great advice, and there are so many pieces to what you said. One is a kind of curation of self, that we don’t get to forget ourselves when we’re doing online dating. It’s really, really part of the experience. There’s been research and I’d love there to be more research on this, but this is something I have really found to be true. That when we get into what I call swipe circuitry, which is that gamification headspace, not only do we not notice the deeper qualities in somebody, but we actually are drawn more to our scratch the itch type.

Research shows that the scratch the itch type is not always the best type. That’s why, in all the work that I do, I say, there’s one key question that we need to askDoes my soul feel safe with this person? Is there a sense of deep safety? The same with ourselves as well. I love the different things that you’re saying, and that you could take a break. When you are not feeling in a centered, good place, you are not obligated to go out there and try to like gather more numbers. There’s a curation and a self-care, which I think is just wonderful. I think that’s a really good point.

Red Flags

I think one of the key red flags for me is if something happens that you feel like you can’t tell your friends about, you know, like someone treats you in a way. That if you told your friends, they would tell you, “Don’t see this person again.” I think the minute you get into that territory, then you need to take a step back. If you can’t tell your best friends about the dating experience for some reason, then there’s something wrong, right? Again, that kind of goes back to being your own best friend.

I love that. That is fabulous. That’s for everyone to remember because we kind of allow ourselves to compromise things that really matter to us, and when we do it and we don’t want to talk about it, then we’re engaging in acts that have a little bit of shame, and that is going to draw us to people who are prone to taking advantage of that. That’s a great point. Charly, can I ask you to introduce your friend here?

I have two dogs. One under the chair and one on my lap. This is Hugo. You can just see him there behind the microphone, and then under my chair, Dudley is asleep. I have two sausage dogs.

Dating Apps Dehumanizing People

Thank you so much for the introduction. I would love to hear your thoughts about kind of there’s a lot of research now that shows that being on dating apps, especially certain dating apps, ‎Grindr is a really bad one for this. I think it’s like one of the worst, but being on dating apps, especially swipe dating apps can increase depression and anxiety for a lot of people because of the dehumanization that occurs.

The key to practical safety in online dating always is to remember that you’re talking to strangers.CLICK TO TWEETThis is actually particularly true in some ways for people of color, and there’s been powerful, powerful documentation of that. Could you just talk about how people can protect themselves emotionally in that way, from the kind of anxiety and depression that come from just being treated in dehumanizing ways?

Yeah. I think this is a tricky part of dating, right, because we’re all being put into boxes. The way that the algorithms work is we get put into boxes. I am definitely feeling it as a 37-year-old female, right? Someone, I had a conversation just this week where someone was saying, “The power has changed when you were a 27-year-old female. You had power over men as a straight female.” Now, I’m in a zone where I clearly, if I want to have kids, it needs to happen soon. The guys know that the power is in their court, and so it is interesting and it affects lots of people in lots of different ways.

As you mentioned, people of color, particularly women of color, really suffer from this, particularly dark-skinned black women are treated appallingly on dating apps because of fetishism, and because a lot of the apps allow you to filter based on race even within the black community. I know there’s a lot of racism internally with darker skin and these concepts, basically these awful concepts, that society has put on us that everyone needs to be a blue-eyed, blonde-haired bikini model.

There’s a lot to unpick in society and there’s a lot then manifests itself when you start to give people boxes that they can take and say, “When people start thinking they have a choice and people start deconstructing people to a list of age, hair color, skin color, eye color, in a way that you wouldn’t actually do if you met someone at the bar, right. If I walk up to you in a bar, you can’t tell how old I am within probably a fifteen-year age gap. I wouldn’t be. I know I can’t age people within at least ten years, right?

I don’t walk around with an age label on my head, and one of the things to remember, if you are feeling like you are being marginalized on these apps is you are not being rejected. The reality is you’re just not being seen because of the way these filters work, people aren’t even seeing you. I saw that firsthand when I turned from 29 to 30 on dating apps because suddenly, I had the exact same photos, right, because they were all about six months old. It was all that had changed. It’s literally within a day, I had ticked over a decade and suddenly, I wasn’t appearing in filters anymore.

People had filtered me out. Quite often, men my own age filtered me out. I really noticed literally overnight, the drop in attention that I was getting. You can’t take it personally because what’s actually happening is you are ticking a box that someone else hasn’t ticked. They’re not looking at your picture and saying, “No, I don’t want her because she’s too old or she’s too ugly or he’s too camp or whatever you’re worrying about.” It’s not even got that far. It will be that they haven’t even seen you in the first place.

It’s remembering that I think, and then I think it’s also really remembering that these tools should, all these tools should be is a form of introduction. They are not telling you your worth by any stretch. This is not a tool to measure your attractiveness to the opposite sex, for example. Dating apps are not a replacement for real-life interaction. They are just an opportunity to cast your net a bit wider, and maybe meet people who you wouldn’t meet in your neighborhood or in your bar or at work.

I think it’s making sure that you frame it correctly in your head, because I think if you try and see it as a replacement for society or some value of your worth and you’re counting your own worth on how many matches you’re getting in a night, no one wins from that kind of thinking and you see that. There are definitely people, and this is one of the things that really angers me about people’s use of dating apps. I love dating apps. I don’t like the way people use dating apps.

One of the things that really upsets me is when people who are not single-use dating apps to, “Let’s see how many people like me.” For example, and I’ve heard married couples doing this, right, where both partners go on an app, like as many people as they can, and then they compete to see who gets the most reciprocal likes. They have no intention of communicating with those people, and they’re just leading people on. You see it a lot, right? There’s nothing that dating apps can do. The dating apps can’t ask, “I need proof that you’re single.”

What are you going to do? “Please prove that you didn’t have a marriage license.” It’s really tricky and you have to trust people. I think that it’s just worth remembering that people, we know this not just from dating. We know this from the whole online world. People are not their best selves when they’re behind a screen, and they think they can get away with something that they can’t get away with in real life. It’s just remembering that, right?

That’s a really wonderful filter right there. If someone, even in that dehumanizing environment, still is human, still is kind, still is connected, extra brownie points for them because that’s really a sign, because you’re walking up a down escalator in order to do that. That’s a real mark in your favor. In developing our app, I did a lot of research and learn just such amazing things like for example, some huge percentage of college men never have an intention when they’re on dating apps to even hook up. They don’t even want to talk. They just want to see how many people, it’s like a boredom relief and a kind of self-confidence booster. There is literally no intention to even hook up or even speak. That’s like a shocking thing. I think that dating apps have been built brilliantly to generate matches, but terribly to create an environment of intimacy, and I think that has to change. I’d love to hear your thoughts on that too, like what can dating app creators do to create more humanity, to create more humanization? I’d love to hear any of your thoughts, dreams and reflections of what could be.

I think it’s quite tricky because the reality is that for a successful dating app, you need numbers, and the way to have numbers is not to restrict your audience too much, right? Anytime you add any form of filter onto that audience, whether it’s sexuality, whether it’s age, whether it’s something more niche like an app for people with a certain type of hobby or religion, you are already filtering down a group that is already filtered because you’re already starting from a point that everyone has to be single, and so the group becomes smaller and smaller.

DDP 112 Charly Lester | Online Dating
Online Dating: In the online dating world, we let our hearts take over from my head. From a practical safety perspective, it’s important to remember those early stages to try to listen to your head and don’t rush into things.


In reality, for me, the ideal dating apps would be ones that made very clear what the intention is that you get on the app, but the minute you start doing that, and I think that it’s tricky because a lot of people won’t admit their intention. I use Bumble and Tinder quite predominantly, and there’s an option where when it asks you what you’re looking for, so many guys say, “I’m not sure. Actually, I want a relationship,” or is that, I don’t want to say I want to hook up because there’s an option to say both of those things.

Then you’re kind of working out where in the middle are they and it’s interesting. For me, it angers me that that’s even an option. I’d rather just it be binary and they had to answer it so at least you knew where they stood. I’ve heard lots of stories that people are saying, “Actually, I met with someone who said, ‘I don’t know what I’m looking for.’” They ended up being in a relationship and they almost had to nudge them over the line.

My most recent date, which was sort of about two, three weeks ago. I went on a date with a guy who it turns out had been very recently single, like literally had separated from his partner of fourteen years, and they’d been separated a month. I sat on the date and the first thing I said was, “I don’t think you really should be dating. I think you just need a friend and maybe, please don’t go on multiple more dates with more women and put more women in these situations.”

It was really interesting because he genuinely, he seemed really quite put out that he had been dating on Tinder, and in his head as a married person who had only ever heard about Tinder, he thought Tinder, I’ll be frank. The way he described Tinder to me felt like free prostitution. He just thought it was an opportunity to just go on there and get lots of sex.

He seemed genuinely shocked that he was matching with educated women between the ages of 35 and 45 and we wanted relationships. It was so interesting, that was how he perceived this app. This is a smart guy who clearly has lots of friends who are women between 35 and 45. We both went to the same university. We’d both gone to Cambridge University. This is a smart guy and you kind of think, “Look at your circle of friends. If you’re picking girls on this app that would have been in your circle of friends, why would their intentions be any different to the people that you already know?”

I think it’s tricky because Tinder’s not going to advertise saying it’s the relationship app, right, because it would suddenly narrow down as numbers, but the reality is and the reason that I still date on it as someone who does want a long-term relationship is it’s the app that everyone’s heard of. You know that if someone is just testing the water in terms of dating apps, that will be one of the first ones they go on because they’ve heard of it. Because eight years ago, their friends did actually have formed relationship on it. It is quite a tricky one because you need the numbers to be a good experience and to have a choice, but in order to attract the numbers, you can’t be too picky and you can’t, as an app founder, you don’t want to be too restrictive in who you’re letting on the app.

That’s a really fascinating thing is what is the win-win between humanity and numbers? What’s the way that there can be a win-win there? I think that playing that game in between draws numbers but creates a lot of pain.

With Lumen, we knew that we were restricting ourselves immediately by putting that age limit on, right? You have to be at least 50 to join Lumen, and we knew we were really restricting that and our investors kept saying to us, “Why don’t you lower the women to 40?” I was really adamant that, “No, the whole reason we were creating it is that women of a certain age were having a real issue being overlooked by men that are their own age,” and that doesn’t start at 50.

I’ll be completely frank with you. I think it starts about 25. Like, literally there’s a point really early on where men suddenly start looking for younger women and the guys at  OkCupid did a lot of research on this. I think it’s basically 22 is the ideal age for a woman for men of any age, which is kind of insane. I saw it firsthand at Lumen. I had men in their 80s trying to chat me up through my customer service profile, and they were literally over 50 years older than me, but it’s interesting. What happens is the older that women get, the larger the age gap the men the same age as them are trying to date on.

Absolutely. Absolutely, yeah.

It’s described almost like an island of women in this book by Christian Rudder. He is the Founder of OkCupid. It’s these women who have just basically been forgotten by their own age group, and so that was why we started Lumen. We knew that not every man over 50 wants to date a 30-year-old. There are men in their 50s who want to date other women in their 50s. By putting that age limit, and the whole point was that we were going to say to these women, “Look, if you come on our app, these men know you’re over 50, and that you’re not going to get overlooked.”

The one thing I will say though is that if you are a really attractive guy, you know you can get younger women. What would happen is the caliber of the women, if I’m being completely frank, the caliber of the women would be a lot higher than the caliber of the men, and then the women would complain about the caliber of the men. You were like, “Well, we’ve got the men who want you. Can you actually meet up with them and see if there’s more than just their photos?” It’s really interesting, right, because people would ask me really early on, “Are older people less picky when it comes to things like looks. No, no one changes.

People are not products in real life, but the way that we see dating apps start to dehumanize people.CLICK TO TWEETHonestly, from the age of 25, we’re all the same. We all use apps in the same way, in the same way that I was saying that there are people looking for hookups on Tinder. People in their 80s were still looking for hookups on Lumen, right? No one changes their attitude that much and no one realizes how old they are. If you asked me off the cuff how old I was, I’d probably say 26 before I remember that I’m 37. If you ask a 70-year-old how old they are, they’re probably still feeling 35 until they remember. We grow up but we don’t, and I think people don’t really change that much regardless of their age.

I’ve kind of devoted a lot of time to this because I think that we are victims of terrible information, and we’re given these breathtakingly sophisticated tools to meet, and no education on the real skills of intimacy, which are the true skills of dating. I just want to say that I think people can learn, and I think that the apps can even teach people, but that’s a very difficult and complex thing, but I think we tend to go for a least common denominator and that has really, really hurt us.

In my work, just like you, I can’t tell you how many women have talked about this as being such an issue. The men want women who are dramatically younger than them. They are like kids in a candy store so often. They just want to have fun. They feel like they can. Women are looking for more serious relationships, and almost like men of that age become more immature in some ways than they were in earlier years. I would just love to hear kind of your biggest learning for that population.

I agree. I think particularly people have come out of a long-term relationship, I think a lot of the men are like, “I’m done. I’ve done that. I don’t need that again. What are my options?” I think it’s one of those things that’s almost become a cliché, but because it’s become a cliché, people then go, “It worked for other people so why shouldn’t I try and do this?” The thing that surprised me the most actually was the way that over 50’s date, men and women, particularly if they are post-divorce or widowed, is if they’ve been married for a long period and they’ve had kids and they’ve done the cohabitation, the thing that actually surprised me was that the type of relationship often they were looking for was more like a teenage relationship where you don’t live with the other person. You just catch up with them a couple of times a week, right, and go to the cinema, and have that more social life with them. The reason for that is they’ve got their own worlds. They’ve spent 50, 60 years building this world that they love. They love their apartment or their house. Why should they bring a stranger into that place?

I thought it was quite interesting this idea that when in you’re in your late 20s, early 30s, it’s all about building that shared world with someone. Whereas by that point, they’re like, “No, my world is built. I’m happy. I like my world. I’ve got a space in it for someone on a Tuesday night to go to the cinema with me, and on a Friday night to go to the jazz bar or whatever they want to do.” They’re looking for someone to fill quite a different role, I think at that age, but that’s not for everyone but that definitely was the thing that surprised me.

Advice On Online Dating

Yeah. That’s so interesting and that does happen a lot and of course, there are so many people who are older, who are looking for a deeply committed, connected, live-in relationship but these are things that are all true and all really different. What advice would you give women in that situation? Let’s say over 50, very aware of kind of what a buyer’s market is for men, how much immaturity there is out there, but who still have hope that there are great guys who are looking for someone like them. What’s your best advice for those women? What are the three key things that you would want to say to them as they enter the world of online dating?

Yes, at first, I would say, be really honest. Be really honest about who you are. Don’t lie about your age. Don’t put filters on your photo. When I was at Lumen, honestly, I can’t tell you the filters that people are trying to put in their photos. We could see it because you have to selfie verify to join the app. We would see what people’s selfies looked like, and sometimes they look 30 years younger in the pictures that they were trying to upload to the app. There’s no point doing that if you want to meet someone in person. Why would you want your first impression in real life to be one of disappointment? Be honest about who you are.

Can I just pause here with a question? Somebody is, they really, really look fifteen years younger than their age. They look twenty years younger than their age and they feel like, “I’m going to lower my amount of people that are interested in me because they judge me by the number age, and not how they would see me when they actually see how I look,” and they struggle with that. I know very, very integrity-based people who change their age from that. Tell me what you think about that.

I mean, you’re starting on a lie and also a very good friend of mine is Maria Avgitidis who’s one of the leading matchmakers in New York, and every Wednesday, she does Ask the Matchmaker on Instagram where she answers these questions. Someone asked that exact question this week. They were like, “I look seventeen years younger so I’m calling myself this age.” She replied saying, “I’ve just looked at your pictures. You don’t look that age.” I think that’s the tricky thing. People think they look a certain age. I mean, how do you decide what age you actually look?

In reality, again, you’re setting yourself up for a really awkward conversation at some point. You’re either going to turn up and they think that immediately they’re like, “That person lied about their age.” Even if you do actually look the age, I mean, why would you want to pretend to be that much younger? If they’re matching with, it depends, doesn’t it? If it’s someone actually your age who then is like, “You’re same age as me. I thought you were fifteen years younger. I will still carry this on.” I mean, one of the reasons the age is important is in terms of social shared jokes and shared cultural references, right?

The reason I wouldn’t date someone fifteen years younger than me is most of my cultural references won’t make sense to them, and this is why it blows my mind when people try to date someone who is significantly younger than them, because I kind of think, “You need to be in that shared space.” A big part of partnership is actually just being in the same place in your life and understanding each other’s lives, right? I think that by lying about your age, then it’s going to get very confusing if you all having to try and pretend that you’re fifteen years younger when you don’t understand half of the references.

Good point. I mean, I think that there are intergenerational relationships that work wonderfully, and it’s a spice for people that they’re like entering a new land of the other person’s culture, but I think the point that you’re making, it’s almost like a metaphor for a mistake people make in dating which is, I’m going to be what I think you want, and then ultimately you’re going to have to see that that’s not who I am. That’s my interpretation of what you wanted. I’ve wasted a lot of time finding someone who’s not looking for someone like me.

DDP 112 Charly Lester | Online Dating
Online Dating: One of the problems of dating applications is that people have become products. 


I think one of the big parts about growing up is becoming comfortable in your own skin, right, and realizing who you are. For me, and this is why I’m still single and I say this, “I’m not going to settle. I’m not going to settle to someone that doesn’t match who I am, and I’m not going to pretend to be something that I’m not to try and attract someone. I could have easily married some millionaires when I was at Cambridge if I had quite happily not had an opinion and tucked under someone’s arm. That’s never going to happen in a million years with me, right?

I could be far richer if I hadn’t been outspoken for the last fifteen years, but I have and I’ve got opinions. I like my opinions and I like firing off opinions. I like the banter, of debating stuff with a partner and actually feeling like an equal in a partnership. I think it’s really vital to be yourself. Being yourself is my first advice to these over 50 ladies. My second piece of advice is to give the other person a chance. For a start, men’s profile, and I can tell you this because I saw thousands of them. I saw what women looked like and I saw the dating profiles.

Men are really bad at creating dating profiles. They do not know how to sell themselves. They don’t know how to take pictures, whereas women go the opposite direction and almost market themselves too well. Men are appalling marketeers for themselves. A lot of them won’t admit it. One of the reasons I realized that this is the case. Women will enlist the help of friends. Friends will take their pictures. Friends will tell them what a good picture is. They’ll tell them what sounds good in their profiles.

Men don’t want to admit to their friends that they’re online dating, and so they try and take the pictures themselves. They have five photos that all look exactly the same, taken at the same time and place. Normally an angle on their chin, then you can’t see their face or it’s really badly lit or they’ve got sunglasses on or they’ve got hats on them. You can’t actually see their face. Men don’t realize how to make themselves look not just good, but just look like themselves.

This is something that I was constantly telling the women on Lumen, “Please don’t be too picky. Give these people a chance. Meet them in real life. Have a video call.” A fifteen-minute video call, you’re going to get a feel of whether actually someone does look exactly like the pictures or whether they actually did themselves an injustice with the images that they chose.

Yeah. I kind of say that all the time is like when it comes to character, be even more fiercely discriminating. When it comes to things like that, soften your focus a little bit to see. Yeah, really true but I think what you just said about men is probably not so true about gay men, right?

No, and I was thinking that as I was saying it. They were straight men. I think gay men know how to market themselves definitely. It’s the straight men who don’t. It’s the straight men who won’t admit they’re dating online I think. My third point is just really on general safety, particularly with women. Women over 50 are the most targeted by scammers, so really keep your wits about you, and that includes things like asking to do a video call really early on to see that they are the person in their photos, and asking to meet up in real life and again, in a public place and in a nice safe place.

If someone starts giving you excuses why they can’t meet up with you in real life like they’ve suddenly left the country, which particularly at the moment is questionable, right? Back in the day, one of the main excuses that scammers would use is that they were in the military and they were abroad for the military. I think really, really keeping your wits about you. If the app that you’re using offers verification. With Lumen, we would use these selfies to make sure that they were the person in their photos, and some of the apps will offer verification with ID.

RealMe, who is the company that I work with at the moment, what they do is that they actually offer the apps. They don’t work with consumers. They work with apps and they allow the apps to do things like background check people, and tell you if someone has a criminal record or if someone has lawsuits pending against them. There are different levels of this verification and the information that you can get about someone, but even if the app that you’re using doesn’t offer those things yet, be smart.

Go off their site and google that person. I do this regularly. If someone tells me, “This is my job,” well then I’ll go on LinkedIn and I’ll check their name and their job just to see actually this lines up and they’re telling the truth. It is very hard these days to not have some kind of online paper trail about yourself and I’m quite open with guys that I’m matching with. If I can’t find much about them, then I’ll just say to them, “Sorry, can you tell me your surname?”

I know that if you type “Charly,” the way I spell it, if you type that in on Google with “dating” or with “journalist” or even with my university probably, my profile will come up. It’s so easy for them to find out who I am before we meet in real life so why shouldn’t I have the tools to find out who they are? If they don’t want that and they don’t like that, for me that’s a red flag. No one should be ashamed of who they are to go on a date. What are they going to do if I’m going on a date with them? Why would they not want to tell you their full name? I just find it bizarre.

Absolutely. Yeah, and on a character level, that applies also, like really keeping an eye out. How does the person talk to you? Are they a little bit rude? Did you hear them yelling out to somebody in an insulting way like to the delivery person or to whatever? Really watch for those signs because I think we really underestimate that, too and then emotionally, we end up getting really hurt when we deny those warning signs or ignore them. I guess that’s really true all around and I think this way of framing it, remember this is a stranger. Remember this is a stranger. Even if that person was referred to you by someone else you know, this person is still a stranger.

I think that real-life quality like you mentioned, I think that’s so important. I’ve heard a lot of people over the last eighteen months falling in love with someone over Zoom calls. I’m sorry but until you are in the same room as them, you can’t smell them. There are the pheromones, there are things like that that you’re not going to realize if you’re attracted to do them properly until you’re in the same room, but also how they talk to other people is so vital if.

If you feel like your mental health is starting to decline and you’re drained, take a step away.CLICK TO TWEETThe minute you sit down in the restaurant with them, if they’re rude to the waiter, you’re suddenly going to view them so differently to when you’ve been one-on-one with them for the last eighteen months on Zoom. People behave really differently in different settings, and I think it’s really important almost to test the water, right? If you’re planning different dates, plan dates where you’re going to see that person in different situations.

I am a big fan of escape rooms. I have been for years and I quite often go on first dates in escape rooms because that is seeing someone in their emergency mode, right, in a high pressure, stressful and seeing how they react, right? If they’re shouting at me and losing it, then that’s not someone I want to be in a relationship with, and I love when I say this is a bit of a litmus test. It really is and you start to see what people are like under pressure.

Some of the best dates I’ve been on have been ones where something has gone wrong, and then you see how that person reacts to that thing going wrong like the tickets they booked were for the wrong day or they can’t get a table at the restaurant they wanted to. Seeing how someone reacts when stuff isn’t perfect. If you want to have a relationship with someone, then you need to know that when things go wrong, that they’re still someone that you like. Otherwise, again, it’s a red flag.

Charly’s Fire

It’s so essential. My dear friend, Hara Marano who’s the editorat-large of Psychology Today says there are three Cs when it comes to making a choice about the relationship. The first is character, the second is character, and the third is character, and I really agree with that. Charly, you’ve shared so many wonderful things, and I have one other question for you. You are obviously someone who gets on fire about different things. You’re obviously so passionate about different subjects. You’re an entrepreneur and you’re an athlete and you’re visionary and you’re a humanitarian. What these days is kind of like giving you the most fire? What’s the thing that you’re kind of most excited about in your life, your work life, your personal life? What’s the most exciting to you now?

It’s quite a big question, isn’t it. What am I most excited about at the moment? I’m a massive feminist. I’m a huge feminist. Anyone that’s watching the video of this recording, I have a big picture of Ruth Bader Ginsburg behind me who I just think is the world’s most incredible woman, and there are lots of Brits who have never heard of her. Literally, her entire story, I find so inspirational. I think for me, the thing that’s getting me most excited is really seeing equality in action. I think we are getting to a point. I mean, we’re still not there and this isn’t just women. This is the whole LGBTQ community.

It does feel like in the last five years, we’re really starting to see steps have been formed in terms of equality, and particularly racial equality in the last year with everything that’s happened in the States. I feel like there are conversations happening that weren’t happening even twelve months ago, and I think that it’s awful the situations that have happened to get us to this situation where we’re actually talking about things. What I like is that these topics are repeatedly coming up first and foremost.

I don’t know if anyone follows soccer. I’m not a football fan. Obviously, Britain is huge for its football but the British team, the English team have been taking a knee in the tournament, and you’ve got some of our politicians refusing to watch the football because they’re so offended by it. I mean, they are racist. I’m sorry. You’re a racist if you’re that offended by someone taking a knee, but it’s really interesting because the main demographic that watch that sport in the UK are not educated. They’re not people who will have these conversations about racial equality.

They’re not people who this would have been a topic on the agenda for, but they see their idols taking a knee and I can’t stand football, but actually something like that, I just think is so powerful because these are not people who listened to scholars or politicians. They don’t tune into radio broadcasts talking about these topics but they’re tuning into the football. They’re coming away and talking about race. At the moment, obviously, this is where we’re recording in two days’ time during the European final.

The team that has got to that final, I think 8 out of the 11 would not be on the team if it weren’t for immigration and that’s a huge deal. As they say in Hamilton, “Immigrants, we get the job done.” I say that as a half Romanian Brit and I love that. I love that people are saying, “Look, all these racist people in my country who were voted for Brexit in the last five years are suddenly going, “Hang on. Actually, we need Europeans in this country because we wouldn’t have a football team without them.”

That’s what I’m passionate about actually is working out, how do you inform people who are not as well-educated, who are not as well-informed? Because I feel like we live in an age where and we’ve seen this with the elections on both sides of the Atlantic where the uneducated and the misinformed can be really used as tools by nasty higher powers. Actually, finding ways to communicate with them on Cambridge Analytica or on Facebook, and finding ways to show them simple messages, that for me is really powerful. Taking the knee at sports events is a way to do that.

That’s wonderful. You know, for me, it’s just been such a painful polarization to witness in my country, and hearing this perspective of people’s having their eyes opened who wouldn’t have otherwise, that’s very reassuring to me and I haven’t thought of it in that way. Thank you for that.

It’s tricky, isn’t it? Because we live in our own bubbles. I imagine you live in a very similar liberal bubble to the one that I live in where our social media becomes an echo chamber because you’re only hearing stuff that you believe, too. We saw this really happen 4 or 5 years ago with the Brexit vote, where everyone that was voting to stay in the EU just thought that would be a landslide vote because that’s all we had heard and seen, and then suddenly on the day, it was 48% of the country believed the same as I did and 52 did not.

Even if those 52 didn’t necessarily know what they were voting for, it was heartbreaking. It really was and I think that was the first time that a lot of my generation, in particular, really realized, “Hang on, we’re living in this echo chamber.” Particularly, I live in London. I live in the capital city. We’re in this very liberal bubble and the rest of the country does not believe the same as we do, and I think that’s been a real eye-opener.

DDP 112 Charly Lester | Online Dating
Online Dating: Excellent skill in an entrepreneur is developing a solution for problems if you keep seeing the same thing in multiple places.


Yeah, joining hands with you across the ocean. Absolutely true. It’s so profound. Thank you for bringing your humanity and your passion, and your spark to all of these different subjects. This was just wonderful and helpful. I want to ask, how can people who want to follow you, follow your passions, follow the projects that you’re doing? How can they learn more about you, stay in touch with you, and follow you?

My two main platforms are Twitter and Instagram. I’m @CharlyLester on Twitter. Charly is spelled C-H-A R-L-Y. I think I’m @Charly.Lester on Instagram because I couldn’t get the same handle on the two platforms but I’m pretty easy to find, to be honest, as I’ve realized whenever I’ve gone on a date.

That’s wonderful and all of that, all the links are going to be in the transcript as well. It was a joy connecting with you, and if there are any last words you want to share with our listeners and viewers, what would those be?

One of the things I mentioned early on is this RealMe product, right? This is a team of people I’ve been doing some work with, and they are trying to change the dating industry from the inside really by trying to demand that dating apps include more safety. I think as users, if you are feeling unsafe with a dating app, with a dating site, speak out, like literally go to the founders. Go to the company and say, “Look, I want to be doing more.” That doesn’t obviously have to be just using RealMe. There are lots of different safety options out there, but if you’re not seeing safety provisions on a dating app or site that you’re starting to see on other sites, speak out about it because our love life, it’s not just our love lives that they’re looking after. It is on safety.

I say that as a consumer, right, as someone using these apps too. If there’s something that you want, go to the providers and say, “Look, I don’t feel safe because of this. I want you to do more background checks. I want you to offer me a blue verified check so I know someone is who they say they are.” Because I feel like they make a lot of money from us as consumers so we have the power in numbers, right? As I was saying earlier, if they don’t have us in numbers, they don’t have a product. The dating apps need you as dater to tell them what you want from them.

Beautiful. That’s wonderful advice. Thank you for everything, Charly, and it was great to have you on the show.

Thank you so much. It’s been a pleasure.

Bye, everyone.

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