Expert Relationship Advice: FAQs on Long-Distance Love, Dating in Your 40s & 50s, and Moving On

Hello everyone, I am widely known for helping people find love. In this article, I answer your questions about relationships, drawing from a recent Q&A session where I addressed topics like starting a long-distance relationship, finding love in your 40s and 50s, and moving on from unrequited feelings. These insights are designed to help you navigate your love life with confidence. For more free advice, sign up for my newsletter, where I send out practical wisdom and ideas every Friday to help you find love or heal from lost love—it’s completely free, and I’ll leave a link in the description for you to join us!

1. What Are Your Top Tips for Starting a Long-Distance Relationship?

Question from Kelly Mares: What are your top tips to starting a long-distance relationship?

Answer: Firstly, be very careful about when you start calling it a relationship. There’s nothing wrong with meeting someone online through the apps, someone long distance, and having this kind of fun, flirtatious connection that starts to build, but in that time period, it probably isn’t the right thing to call it a relationship unless you’ve explicitly had that conversation. It would be strange if you had it too soon—could even be a red flag if someone is saying that to you too soon. Don’t let the desire turn into a reality in your mind that you’re now in a relationship when the two of you have never actually had that conversation, because I’ve watched many, many hundreds of people give to this situation like it’s a relationship, be exclusive, give time, give energy, give effort, make trips, when the other person is not behaving like they’re in a relationship at all, and they never really had that conversation—it just became this assumption.

If you feel you’re in a relationship, I would start by having the conversation so that you’re both on the same terms: “Hey, do we both feel the same way? For me to continue giving to this, it would have to be on the basis that we’re really giving this a try as a relationship and that it’s an exclusive one.” Once you set the ground rules for that, okay, both of you have said yes to that, now you’re in a long-distance relationship, and at that point, it becomes a kind of “how do we navigate the difficulty of something that feels wholly unnatural, which is we’re trying to have an intimate relationship at a geographical distance?”

Firstly, there has to be a time on the horizon where you know you’re going to see each other—you’ve got to have something to look forward to. As the relationship progresses, I would argue that there needs to be some kind of a vision for how you’re going to solve that issue in a sustainable way. You know, what does this look like in a year, in two years? Are we actually going to be in the same place? That doesn’t have to happen on day one, but there does gradually start to have to be a vision for, you know, how does this problem get solved? Otherwise, we’re in a relationship where neither of us are actually taking on the reality that we haven’t solved it, and maybe we haven’t solved it because neither one of us is actually willing to do what it takes to permanently solve this situation.

In the meantime, when you’re trying to navigate it, I would say mixing up the energy that we bring to the table is very important. It’s very easy for us to say, “I am long distance, so the kind of energy I give when I’m in the same room as someone, especially romantically, is off the table.” Instead, I’m just going to do what I can do, which is have very long, in-depth conversations, but if you think of any relationship where all it is is one note of very long, in-depth conversations, eventually it’s going to get boring, it’s going to get stale, it’s going to feel staid. So we have to mix up our energy. Are you being flirtatious? Are you still bringing your sexuality to the table, obviously in ways that feel safe to you? Sending nudes and things like that represents real challenges and risks when it comes to potentially breaking up with someone or someone you can’t trust, so that’s a whole different subject, but still bringing your sexual energy to the table, still bringing your playful energy to the table. Can you have a 60-second funny voice note or call, and a three-hour spending the evening together talking for that long? Can you be both?

The last thing I’ll say about this is there’s being together in conversation, and there’s being together in company. When you think about a relationship, sometimes you’re having conversation, and that’s quality time; other times, you’re just in company with someone—you’re sitting next to each other on a sofa, reading or watching a movie. It would be hard work if quality time always meant being in conversation. If someone learns to associate that the only way to connect with you is to have conversations with you, they’re going to start to feel the stakes are really high anytime they want to be with you or around you because it’s going to involve trying to have a conversation, and you know, at a certain point, you will run out of things to talk about—that’s just natural. So it might be time to be in company with them. That might mean hitting play on a movie at the same time from a long distance and watching a movie together and then talking about the movie afterwards. Don’t just be conversation—pick times to be in company, and that will lower the stakes for the time that you spend together. It also means that time spent together doesn’t always have to mean time away from other obligations and responsibilities that both of you have.

2. Is There a Connection Between Physical Pain and Love or Vulnerability?

Question from Glory Be Free: Do you see a connection between the physical pain you endured and the new found level of love and vulnerability you orient from?

Answer: Firstly, that’s a lovely compliment—thank you. For those of you that don’t know, I write in my new book Love Life about my own journey with physical chronic pain and how it lasted for many years—part of that I still have, so it’s not completely gone away. It certainly did kind of crack me open. I think every challenge we have, every challenge I’ve ever had in life, has been an invitation to a greater degree of compassion, not just for myself but for other people, because I think every time we go through a challenge, we get more connected to what other people go through in life if we can kind of widen our lens and not just see it as our pain, ‘cause of course none of our pain is original—other people have experienced it, are experiencing it. I always find any challenge gives me a window into the challenges that other people have faced or are facing, and that’s made me a more compassionate, loving, humble person every single time.

My chronic pain was, I suppose, in some ways my first encounter with something that truly made me miserable that I didn’t know how to change. I didn’t know how to make it go away, and I had to change my relationship with it, and that was one of the most humbling experiences of my entire life and was also, in many ways—and I’m not someone who throws this word around lightly—it was a spiritual experience to come to a place of acceptance with that. So yes, I think that probably, I don’t think it’s the only thing that’s made me loving and vulnerable, but I do think it gave me access to a depth I hadn’t had access to before when I felt like I could always fix my problems, and in this case, I couldn’t fix it. I had to change the impact it was having on me by changing my relationship with the challenge itself.

3. Why Am I Obsessed with Looking for Things Wrong in My Relationships?

Question from Marie Cooper 35: Why am I so obsessed with looking for things wrong in my relationships, things that will hurt my heart, like looking at their exes on social media and then overanalyzing everything?

Answer: On one hand, it might be that there’s a familiarity for you in looking for those kinds of things, that simply sitting back and enjoying the peace that you might feel right now is deeply uncomfortable and it’s unfamiliar, which is why it’s uncomfortable. Instead, going and looking for something that creates drama, gives you something to feel jealous about, gives you something to feel insecure about, is much more familiar, and we’re drawn to what’s familiar, not necessarily to what makes us happy.

I want you to imagine that so far in life, your behavior in dating is like a vinyl, you know, like an old record, and that the groove in that vinyl that plays the song a certain way has been established, long since established. So when you go on another date or you start seeing someone you like, what happens is you put the needle on that record, and that record starts to play because it’s the groove that you established a long time ago. You don’t necessarily have access to a different record right now to play because you haven’t established those grooves, but you can. It requires conscious practice. It requires awareness of, “Oh, I’m going to look at this person’s profile right now and dig deep into who they’ve been with before or what their exes are like or they have that I don’t,” as a kind of compulsion, because that’s the record that I’ve been used to playing. I’m used to feeling these feelings of jealousy, of anxiety, of tension. I’m not used to not doing that and feeling a sense of peace.

If I become aware as I’m about to do that, that that is a behavior that I feel drawn to, not because they’re doing anything underhanded, not because they’re behaving badly or they’re giving me reason to be suspicious, but because that’s the way the record plays for me, that’s the groove I’ve worn in over time, when we get conscious of that, we become able to take a different path. It may be that that path in the past has served a need, maybe the need to feel safe, and that that hypervigilance that has you looking for problems so that you can go and meet them instead of them surprising you—it’s something that’s made you feel safe; it’s felt like a form of control. But maybe these days, you’re ready to accomplish a feeling of safety in a new and more productive way, for example, in just having trust in yourself that if anything were to come to light that would reveal this person wasn’t a good partner, you would be able to walk away, that you don’t need to anticipate every problem—you just need to show up as the best version of you and pay attention to the present and to what you’re actually seeing from this person, not trying to anticipate everything they could be or do in the future.

4. How Can I Find Love in My 40s and 50s?

Question from Grizzle 101: Would love to hear more tips and advice for dating in our 40s and 50s. Everything seems to be targeted towards the younger generation. Why is it so hard to find love again, and what can we do to become our best self to attract a partner?

Answer: I have always maintained that the things that I say are applicable at every age. I don’t think that, even when I’m talking about things like flirting, often people think, “Oh, that’s, you’re talking to younger people there,” but of course, what makes us attractive at any age is the ability to both be sincere but also be playful, the ability to be flirtatious, to not lose that energy. So I would challenge you to ask yourself, what is the part of what maybe I’m saying that you don’t think applies beyond a certain age? Because I think the fundamentals apply at any age.

If you’re in your 50s and you have come out of a long-term relationship or a divorce or perhaps you’ve just struggled to meet someone in your life, the fundamentals are the same. How active is our life? Is it the kind of life that brings us into contact with other people? A lot of the time, the older we get, the more our life contracts. We get into these routines and rhythms that can become quite staid; they’re very comfortable to us, but they may not be the kinds of routines that actually engage us socially with people that we don’t already know. So, do our lives include communities, environments, events that bring us into contact with new people? Are we being brave in those areas? Because it does require some bravery.

The last thing I would ever tell you is that it’s easy, because the reality is, many people do experience feeling more invisible, feeling like they don’t have nearly the same amount of attention that they had at a different stage of their life. I think, for that reason, we have to find ways of enjoying the process, because otherwise, we’ll never do the things that bring us into contact with opportunity. What are the activities that I might like to do, regardless of whether I meet someone, but by doing those activities, I might actually meet someone? What are the ways I could engineer my life to build myself into more and new communities, that I could meet new single friends, I could meet different types of people than maybe I’ve encountered in the past?

Not over-relying on only one thing, like a dating app. It’s very tempting to get into the comfort of a dating app, but then it can be very demoralizing when we find we’re not getting matches or the kinds of people that are matching with us are people that are sleazy or they’re not our type of person or scamming us, which is very common these days. It could be extremely demoralizing, which is why I say you can do those things, but don’t make it your only source of new people in your life. That’s what we do, again, from a place of comfort and not actually putting ourselves out there in the real world.

I do empathize with what you’re feeling and what you’re going through. It’s hard when we’re not where we want to be at a certain stage in our life, and we feel like it’s gotten harder in the process. But I also want you to entertain the idea that at least a part of that is not all of it—because some of that difficulty is real—but at least a part of it may be a story that we’re telling ourselves about how it’s impossible, it’s never going to happen, or no one is ever going to want us. Instead, consider the idea that if you just woke up into your body right now at the age you are and you felt the desire to meet someone without any of the baggage of the past, you might take a different approach and have a different energy towards going out there and meeting someone, and that energy might be the reason that you do meet someone.

5. How Do I Move On from Someone I Never Dated?

Question from Min Yuni 7: How to move on from someone you have never dated? Feelings for him are so strong that it feels something is dying inside.

Answer: I’ve spoken about this at length in my book Love Life—for anyone who hasn’t got a copy, I strongly advise you read Chapter 2, “How to Tell Love Stories,” because in it, I talk about the value that we’re placing often on the wrong things, that a real relationship is so much more than the story that we invent about how important a person is. I have a much more backwards-looking approach for relationships than forwards-looking. In other words, a forward-looking approach is, “Look at all the potential for this person, look at all the potential for how happy they would make me, look at what we could be together,” and that is, by definition, a projection of a future that does not exist. So we could be right, I guess, but we’re only right if that future that we have anticipated actually happens. If it doesn’t happen, then we were wrong about how important this person was.

Whereas a backwards-looking approach is saying, “Look at how extraordinary this person is who is in my life, all the ways they have shown up for me, look at what we’ve built together—wow, this is an important relationship, wow, this is an important person in my life,” and you don’t need your imagination for that exercise. You are saying it because it’s true, because those are the facts. I would argue that in order for you to feel like something is dying inside right now, you need a lot of imagination, because there’s an imagined idea of how important this person is in your life when they’re not living up to that idea at all, or the two of you would actually be in a thoroughly fulfilling relationship with each other.

Once you realize that your pain is not actually coming from the importance of this person but from the importance of the story in your mind, you can start to see that story for what it is—a story—and separate from it and observe it, kind of in the same way that we do with our thoughts in mindfulness practices, and start to realize that the story is making it painful, not the reality.

6. Why Did He Say He Wanted a Serious Relationship but Then Back Out?

Question from Anna: Why a guy was telling me from the beginning he wants something serious with me, and after 2 and a half months, all of a sudden he said he is not ready for a relationship?

Answer: Well, there could be many reasons for that. Maybe he got over-excited in the beginning and couldn’t back it up. It might be that he himself got excited about the possibility of a relationship, but the reality of a relationship was something that wasn’t really ready for, in which case, after 2 and a half months, he did you a giant favor, ‘cause it’s better that you learn that 2 and a half months in than a year in. That’s the case for a lot of people, is that they get excited in the beginning—especially, it’s a sign of real immaturity. It can also be a sign of manipulation, of course, that’s, you know, telling someone, “I want something serious,” even when I don’t because I just want to get something from you.

But it can also be a sign of immaturity: “Oh my God, I feel so strongly, I’ve never felt like this, I haven’t felt like this in such a long time, you make me feel amazing, I want something serious with you,” especially if he felt like you were kind of, you would only be into him if he wanted something serious, and maybe felt you pull away a little bit, and he was like, “No, no, no, I want something serious with you, I can’t lose you.” There’s an immaturity to that if the reality is he’s not available for a real relationship. When it comes down to it, he starts noticing that a real relationship means that he actually has to get to know you, not just your projection. He has to be known, he has to actually share more about himself instead of just being the heroic version of himself.

When someone who is immature about love and isn’t ready for an actual relationship, just the feeling of a relationship, they may initially get excited, and then when those things start presenting themselves, when having a relationship actually requires a few calories, all of a sudden, they get completely overwhelmed by the reality of a relationship. It sounds like 2 and a half months in, either he had been in manipulation mode or he had been very immature about his version of love or his idea of love, and he couldn’t then back that up when a reality of a relationship presented itself.

The other alternative is that during those two and a half months, he discovered that it wasn’t right for him for whatever reason. That doesn’t mean it’s anything to do with you—can be many, many reasons something isn’t right for someone that aren’t to do with you, and that it was easier to tell you that it turns out he wasn’t ready for a relationship than to tell you that he didn’t want a relationship with you.

The important thing for you to realize is that someone has made clear their intentions. All you need to do is look at the situation and go, “Is there anything I would like to do differently next time? Did I bring my best self to the table?” And if the answer is, “No, I didn’t, I’d like to do some things differently next time,” then this was a gift in giving you that insight. And if the answer is, “No, I brought my best to the table, this person just misled me about their intentions for a relationship or decided I wasn’t right for that relationship,” then I need to grieve the disappointment and keep moving forward, because the right person for me will last longer than 2 and a half months.

Anna, if you haven’t already, I would suggest that you go and check out Dating with Results. It’s a free training that I put together to help you seek out healthy, mature people who are ready for a real relationship, avoid the people who are not, and certainly see the early warning signs that someone is not, and have the conversations along the way that actually lead to something real. For anyone out there dating right now, if you want to date productively, if you don’t want to waste your time, if you want to find the kind of love that you’ve always been looking for instead of just more casual dating or something that presents as very exciting but then disappears as quickly as it came, this will be one of the most valuable hours you could spend for your love life, and it’s free. That’s at Dating with Results—I’ll leave a link in the description for anyone who wants to check that out.

Final Thoughts

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