In this YouTube conversation, Matthew AI and several speakers respond to a listener, Cheryl, who worries she may die without ever experiencing a lasting, loving romantic relationship. Drawing on literary (Gandalf’s counsel to Frodo), philosophical (Bhagavad Gita), and personal anecdotes, the participants explore how to hold the possibility of never finding love without letting it dominate one’s outlook. They argue that catastrophizing the worst‑case scenario narrows the perception of life’s breadth, while adopting a “everything is a bonus” mindset reframes each day as a gift. The dialogue expands the definition of love beyond romance, emphasizing non‑romantic, familial, and community bonds, and asserts that everyone is entitled to give and receive love. Practical suggestions include: practicing gratitude, avoiding harmful comparisons (e.g., idealized wedding videos), seeking diverse role models who have found fulfillment outside traditional marriage, staying curious about what attracts us to others, and taking small, courageous risks in dating. The conversation ends with a brief plug for a dating‑solution website. Overall, the talk offers compassionate, philosophical, and actionable guidance for navigating loneliness, fear of never finding love, and building a meaningful life regardless of romantic outcomes.
Chapters
Foreign.
There's a woman here named Cheryl who brings up a topic that she says we've never addressed. And she says in an email, you always create hope and optimism, but you've never addressed the distinct possibility that we may go to our graves without ever having found a lasting, loving relationship. I am 51, divorced after 20 years to someone I never loved, not even at our wedding. I've dated steadily since with an open heart, lots to give, and great communication skills. I won't stop trying. But I have to also hold the notion that I may possibly die without ever having had a lasting, loving relationship. And that's from Cheryl.
Hmm, that's heavy.
I always think of Gandalf's words when he says to Frodo, in the minds.
Of Moria and just love how seriously you're building up to this.
Frodo says to Gandalf, I wish none of this had ever happened. Gandalf says, so do all who live to see such times. But that is not for them to decide. All we have to do is to decide what to do with the time that is given to us. And that line, for me, it just is the answer to this question that anyone who suffers grief, anyone who suffers tragedy, anyone who suffers serious loneliness or despair or pain will have gone through a moment where they say, I wish this hadn't happened to me, or I wish life was different. And, and that's understandable, but it's not our job to reorganize the universe that we're in. It's our job to make the most of. Of the time we have and the possibilities that we have. Cheryl, no one knows for sure whether you will find the kind of love that you are looking for. The only thing you can resolve to do is to make the most of the time that you have to invite as much possibility into your life as possible, to be courageous and take a few risks along the way wherever possible, and to then see what unfolds in your life as you do those things. We have to resist the urge, and Audrey has to remind me of this sometimes. But we have to resist the urge to catastrophize because for the traumatized among us and for the people that have been through certain things, you. You will find yourself in life routinely and reflexively looking at the worst possible.
Case scenario unless you're doing it in a very meditative, stoic practice way.
Well, yeah, to hold it as a possibility is not the same thing as to exist there.
And I think that's their point.
To anxiously ruminate about the the worst possible outcome, because there's a good chance that the worst possible outcome won't happen. And if you only exist in that outcome, then you're not existing in the full breadth of. Of possibility of what may happen in your life. You're 51. You know that there's a whole lifetime ahead of you. You know, if you live to be 100 or near 100, you, you're at the halfway point. So there's time. There's time and there's so much possibility. And so seeing where you're catastrophizing is important. Yes, there's the possibility you might die without having had a lasting, loving relationship, but I, by the way, I bet that's not true for every part of your life. I bet there have been some lasting, loving relationships in your life, even if they haven't been romantic. And that counts for something. That's real. That's real. And it's also worth saying to yourself, I always, I always think there are people that I thought were incredible whose lives, at one point or another I might have said to myself, oh, I trade with them who then took their own life and never made it to my age. And when I think about that, I think, well, it from that, looked at from that perspective, every day I get that they didn't is a bonus, because that could have been me. Every day I get beyond the day that they were alive is a bonus. So I can complain about what I'm not getting or what I'm not achieving or what's not happening in my life, but I could also just see it all as upside. It's just all bonus. And you're 51, like, congratulations, you made it further than so many people ever make it. And you didn't. You weren't born in, you know, 1584 and got slaughtered in some horrible war by being sent to the battlefield as a soldier with no choice. You weren't someone who was born in a time where you couldn't even get your most basic needs met, let alone think about finding love. You're you at 51 in 2022, and you have your whole life ahead of you. Everything's a bonus. Everything's a bonus. And look, you know, it's what happens, I think, for so many of us is it's so easy for us to get caught in the comparison with other people's lives. I get it. I get it. For me, I get the worst version of it because I'm in LA and there's people doing all sorts of crazy and achieving Lots and people who are doing amazing things. And sometimes I hang out with people that are my peers and someone's doing something cool or got a new opportunity or writing a new book or something, and there's some part of me that's like, oh, I'm not doing enough, or, oh, I should be doing that, or, oh, I. And. And I can go home almost like feeling like, man, I'm not. I'm not really killing it. I'm not really doing enough. And I realized what's made me happy is looking at what other people are doing. I remember Jonah Hill was. He said. He was asked who his hero was, and he said, his next door neighbor. He said, his hero is his next door neighbor. Because this guy just that he was. He was on his porch one day and he saw his neighbor, and he said, his neighbor's always happy. And he asked if he. His neighbor, what. What are you. How do you stay so happy? And the guy said to him, I don't give a damn what anyone else is doing. Like, I just pay no attention to what everyone else is doing. And there's some real wisdom in that. Because if you just, at 51, see that everything in your life is a bonus from here on out, then how bad can it be? If you go through the rest of your life with unbelievable friendships and people that you can lean on and people that you can help and people that you can alleviate the suffering of and doing things that give your life meaning and purpose, if you never found that kind of Hallmark card version of love, you still would have lived an amazing life. And I get that there's a sadness to what we don't get in life, especially when what we don't get is something that feels deeply important to us. But your life will still have been amazing. And let's just remember something. There are a thousand different versions of the thing you think you want. There's a version of your life from now till the day you die where you have three really meaningful relationships, and they're really special. And they added so much to your life by knowing these people and being with these people and loving these people, even if they didn't last. There's a version of your life where you meet the love of your life tomorrow and they die in a car crash six months later. There's every different possibility laid out in front of you right now. You're taking the one possibility of which, by the way, is only one possibility out of an unbelievable number of possibilities, but you're taking the one possibility that you go the rest of your life without meeting someone that stays with you for the rest of your life. And focusing on that and saying, if that happens, I will have lived to no effect or I will die an unhappy person. I refute that argument. I don't believe that's true. I believe you can live an extraordinary life without that happening. And that's in your mind, the worst case scenario. But there's every other possible scenario, and by the way, there's every other possible scenario of love for you and what it could mean and how you find it and how long it lasts. And all of them can be wonderful in their own ways. There's also a scenario where you get diagnosed with a terminal illness tomorrow and you have six months. And then how much are you thinking about the 30 years that you spent, quote, alone and not in love? All of a sudden, none of that matters. All of a sudden your dream would just be that you get those 30 years that would suddenly become the ultimate, is that you got to stay here. So that that perspective is really important. The not catastrophizing is really important. The everything is a bonus mindset is really important. And one thing I would start by doing if I were you is I would find some role models that are different to the previous role models because you may have had role models along the way that are all married by now and have kids and are doing their own thing and they're doing this whatever. Find some role models that are not. Find some role models that are happy without that. Find some role models that met the love of their life at 75. Find some role models that took a different path. Because when you find other role models that have lived different paths than the very kind of specific stereotypical path that you've based your happiness on, you start to realize how many different directions and paths happiness lies on.
I think there are so many forms of love we can express in our lives, and I think that's what we underappreciate, is how much love we have inside of us and can give in so many myriad ways. And you know that Bhagavad Gita quote, like you're not. You're entitled to the labor, but not to the fruits of your labor. And in a way, it's like you are entitled to love, to like give love, spread it, be a force for love in every way in your life. And you can't always guarantee what relationships that will or won't lead to, whether they last, what happens. But you have the entitlement to love.
That'S really good.
I would just add one thing here. I want to put the impetus on you for a second, Cheryl, to just be. To just stay really curious about what it is you're attracted to in people and what you love about people. Because I do sense with this, you. You say here divorced after 20 years to someone I never loved, not even at our wedding. I've dated steadily since with an open heart, lots to give, and great communication skills. It is possible to just take that at face value. But I do worry that it's not fully an open heart. I think that I've met people like this before, and there is a sort of. It's like you were saying about comparison, Matt. I used to shoot weddings, and you see the weddings where it's like, people are. So I'd make videos out of these weddings, and you make this ridiculously loving montage in the wedding video. And, you know, the bride takes that wedding video and shows it to all her friends, and all their friends are just comparing themselves to that bride and that. That love. But that Sam Smith song playing at this crescendo of the first dance or whatever, and it's just impossible to compare. It's impossible. I'm never gonna. I'm never gonna achieve that fairy tale status of love. And I. I just worry that people have this idea of what their love life was supposed to be like. And it's. They could have. You know, you could have a date today with someone that they can have a little kindling of magic. But if you're not really curious to, like, give that. Give that kindling a little bit of air and let it grow, you never. It might not be that Sam Smith song at the crescendo of the wedding. It might, you know, it might never be that. Especially at the age of 51. It might not be that young love or whatever, but if you're curious enough about humans and you just want to love and indulge that experience with this really fascinating creature across from you, this primate, you might just find something a little bit special.
I think that's so beautifully put. And I really feel drawn to what you said about weddings. I love the idea that you, their friends see the video, you saw the wedding day, and a wedding. A wedding is already like a peak moment. But the wedding video is the. It's the highlight reel of the highlight reel.
Yeah, exactly.
And to compare yourself to that even. Even. I love that idea that even you. You comparing yourself to that. To what you think other people are feeling in these moments in their relationship, especially if you don't think you've ever had it, you glorify it even more is really, really valuable. Wait a minute. Before you go, what are you about to click on right now? I'll tell you the one that's come up on mine. Wasps in figs. Figs have tiny dead wasps inside them. Now is that changing your life? I know it's not changing mine, but I have something that will change your life. If you go to yourdatingsolution.com you can put in your name, select the dating challenge that most applies to your life right now, and this tool will will recommend one of my solutions that best fits your needs where you are in your love life right now. Check it out@yourdatingsolution.com.
