Dating After Divorce or a Break Up: 3 Steps to Re-enter the Dating World | (#013) Beyond Success: Psychology & Philosophy for Achievers, with David Tian, Ph.D.

Welcome to “Beyond Success,” the podcast for high-achievers seeking deeper meaning, fulfillment and purpose. Now, here’s your host, world-renowned leadership coach and therapist, David Tian.

If you’ve clicked on the title of this podcast, I know you’re someone who has faced big challenges and conquered them. But what happens when the challenge isn’t a boardroom crisis or a major deal, but instead is your personal life, specifically, dating again after a divorce or the end of a long-term relationship?

By the end of this episode, you’ll have a clear roadmap to confidently reenter the dating world, not with uncertainty or awkwardness, but with a sense of clarity, purpose and ease that matches the confidence you’ve built in your professional life. This isn’t about swiping endlessly or wondering if you’re doing it right. It’s about creating the kind of connections that are meaningful, authentic and aligned with the life you’ve worked so hard to build. [00:59.8]

Now, getting this wrong doesn’t just mean a string of bad dates or wasted time. The deeper risk is falling into a cycle of shallow connections or reliving patterns that didn’t serve you in your last relationship, and when that happens, it’s not just your personal life that takes the hit. It bleeds into your work, your health, your focus, and ultimately, your sense of fulfillment in life.

I’ve seen it happen too many times, driven, successful people losing sight of what matters most to them, because they thought that their achievements would naturally carry over into their personal lives. But the truth is, the same strategies that made you a success at work don’t always apply in personal relationships. This is a different game, one that rewards self-awareness, emotional intelligence and intentionality. So, if you’re ready to avoid the traps that hold so many others back to step into this new chapter of life with confidence and purpose, stay with me.

In case you don’t know who I am, I’m David Tian. For almost the past two decades, I’ve been helping hundreds of thousands of people from over 87 countries attain success, happiness and fulfillment in their personal and professional lives. [02:05.8]

If you’re listening now, you’ve clicked on the title of this episode, there’s a good chance you’re feeling some mix of frustration, uncertainty and maybe even a little fear. Let me say this right away—you are not alone. No one gives us a manual for how to rebuild our personal lives after a breakup. For people like us who thrive on mastery or structure and clear results, the messy emotional side of life can feel especially overwhelming.

I get it. About 20 years ago. I was there, too. I had just gone through a divorce and the dissolution of that relationship was the most challenging thing in my life at that time. When that marriage ended, it cracked open something much deeper. Suddenly, I wasn’t so sure of myself anymore. I felt like I was standing in the wreckage of my life, unsure of how to move forward, and if you’re feeling that way right now, I want you to know it’s totally okay and understandable and reasonable. This is all part of the process. [03:05.4]

Fast forward to today, and I can tell you from experience that there is a way through it. I’m now happily married to a wonderful woman, and a proud father to an amazing son. But getting here wasn’t about luck or just moving on. It took work, real work, inner work, to build a new life for myself, to understand what I really wanted, and to reach a deeper level of self-awareness than I had ever even known was possible. That’s what we’re going to unpack today. It doesn’t matter how much baggage you think you’re carrying or how long it’s been or how out of place you feel in the modern dating world. This is your chance to start fresh and I’m here to show you how.

Okay, I’ve got three main points here, so let’s dive right into the first one, how to rebuild your identity and confidence. Here’s the challenge. As high-powered executives or leaders, so much of your identity is tied to what you do, to the results you deliver and to the influence that you wield in your professional life. [04:05.2]

That’s great for the boardroom, but when a long-term intimate relationship ends, it’s got a way of exposing the gaps in how you see yourself. Suddenly, it’s like the mirror gets flipped, and the person staring back isn’t the VP or the CEO or the founder. It’s just you, without the title, without the accolades, without the status, and that can feel uncomfortable.

But here’s the good news: that discomfort that’s your opportunity, because what’s really happening is that you’re being asked, maybe for the first time in a long time, to reconnect with who you are at your core, not just the professional version of you, not the role that you played in your previous relationship, but the person at the core underneath all that. [04:51.6]

Let me share something from my own experience. After my divorce, I came to realize that I had spent much of my life shaping myself around what other people wanted, what I thought I needed to be for them. I was the, quote-unquote, “ideal partner” in my mind, but the truth was, I didn’t really know what I actually, truly, really wanted. I didn’t know what made me happy for real, what lit me up, or even what I stood for truly, and rebuilding my life meant starting with those questions.

So, where do you start? Step 1: reconnect with your authentic, core self. One great way to do this is by reflecting on your values, what truly matters to you, not what you’ve been told should matter, but the things that, deep down, resonate with you. Take some time to actually write these down. Take 10–15 minutes in the morning to journal, or whenever you’re listening to this, if you can put that time aside, and ask yourself, what are the values that are most important to you? What do you stand for? What are you willing to die for? [What] are you willing to sacrifice for? Maybe it’s integrity or creativity, or maybe it’s adventure or connection. [06:05.3]

At first, don’t overthink it. Just let the words come out first. Next, dig into your passions. What are the activities or interests that bring you joy or make you lose track of time? If you’re coming out of a divorce or breakup, probably you have lost touch with those activities that really light you up and it was a long time ago that you let yourself indulge in those.

For some people, this might mean diving back into hobbies that they’ve neglected, like painting, hiking or traveling. For others, it could be exploring completely new territory, something you’ve always wanted to try but didn’t give yourself permission to do it. The point is to let yourself rediscover what makes life feel rich and meaningful to you now at this stage in your life.

Here’s a big one. Get clear on your non-negotiables in relationships. You’re fresh off a breakup, and this is a great time to reassess what went wrong and what you will not put up with in your next relationship. This isn’t about creating some rigid checklists, though. It’s about understanding what aligns with your values and what doesn’t. [07:14.0]

For example, if one of your core values is growth, you’ll probably want a partner who shares that growth mindset. Clarity on the things that are most important to you creates a foundation for healthier relationships moving forward.

Okay, now, reconnecting with your authentic core self isn’t just about lists or exercises. It’s also about healing. A breakup, especially after a long-term relationship leaves wounds, and if those wounds go unaddressed, then they end up showing up in ways that you don’t expect and won’t want. They end up sabotaging you. Maybe it’s overcompensating in your next relationship or chasing external validation or avoiding vulnerability altogether. [07:56.5]

The truth is, confidence doesn’t come from faking it or brushing past your emotions. It comes from owning your story, scars and all, because it’s those imperfections and those detours that make the story most interesting. This means giving yourself permission to grieve the loss, to feel the pain, to let go of the blame, whether that blame is directed at your ex or yourself or the situation.

One practice that’s helped me immensely has been journaling. Journaling isn’t about just writing down your feelings. It’s creating a space to process what’s happened and uncover the lessons that your life is teaching you. You can start with simple prompts, like “What am I feeling today?” or “What did I learn from my last relationship?” The idea is to just keep writing in a kind of brainstorming way, a stream of consciousness, without stopping, and getting to know what’s in your mind more and getting it down on paper so you can see it. You might be surprised by what comes out. [08:56.0]

Now, as you do this inner work, something amazing will start to happen. You stop needing external validation to feel good about yourself so much. Your confidence begins to come from within you. You’re not trying to prove your worth to anyone because you’ve reconnected with it at its source. A breakup or divorce isn’t just an ending. It’s a chance to rediscover and reinvent yourself. It’s an opportunity to create a life and a version of you that feels more aligned, more grounded, more fulfilled, and when you do this work, something incredible happens. You don’t just attract better relationships, you show up as the kind of person who is ready for them.

All right, now let’s get into the second point. Now that we’ve laid the groundwork for rebuilding your confidence and identity, let’s get into something that makes a lot of people’s heads spin these days, the modern dating landscape.

For high-achieving professionals like yourself, this can feel like stepping into a completely different world, and if your last serious relationship started before dating apps or even social media were a thing, it probably will feel even stranger. [10:02.3]

The truth is, modern dating isn’t exactly built for high-achievers. If you’re an older professional who values meaningful connections, swiping through profiles on apps isn’t going to show you in your best light or give you the kind of experience that you’re looking for. Dating apps, by design, prioritize surface-level traits and instant judgments. They’re about gut reactions to a few profile pics and some lines of text. Sure, they might work for some people, especially people who are in their 20s, but for busy professionals who are mature in their careers with limited time and higher standards, dating apps can feel like a frustrating black hole.

So, the alternative is to bring dating into your world, not the other way around. The goal isn’t to mold yourself into the modern dating culture. It is to align the modern process with your ideal lifestyle. [10:56.1]

Hey, if you’re an achiever who’s been struggling when it comes to managing your emotions or navigating your relationships, I get it. So many high-performers hit a wall when it comes to emotional mastery. Maybe you’ve noticed that stress, frustration or anger is seeping into your personal or professional life, or you feel disconnected from those you care about.

That’s where my “Emotional Mastery” program comes in. It’s based on peer-reviewed, evidence-based therapeutic methods to help you find happiness, love and real fulfillment. Learn how to break free from the emotional roller-coaster and start thriving in every area of your life. You can find out more at DavidTianPhD.com/EmotionalMastery. That’s D-A-V-I-D-T-I-A-N-P-H-D [dot] com [slash] emotional mastery.

Let’s start with one of the most underrated and awesome best methods: meeting people in real life in the places you already frequent or enjoy. If you’re part of a members-only club, use it. Social mixers or events at these venues are great opportunities to meet others who already share some of your interests or values. The environment and context itself already helps filter out mismatches, and the connections will feel more organic. [12:18.8]

Another great approach is to leverage your existing network. You can host a dinner party, but with a twist: make it a slightly larger one and ask your friends to bring along a guest who is single and someone they think that you might click with. This works especially well because mutual friends act as a natural filter. They’re less likely to introduce you to someone incompatible, and the setting makes it easy to connect without the pressure of a one-on-one date.

But what if you want to take things into your own hands? This is where the classic cult approach comes in, not the cringe-worthy kind, but the confident, natural kind, which are going to be more akin to who you are as a successful professional. [12:57.0]

So, picture this. You’re at your favorite wine bar or a bookstore, or even just your favorite cafe, and you strike up a conversation with someone who catches your eye. Most people, especially nowadays, are caught off guard by how rare this is. It shows courage, confidence and charisma, all traits that immediately set you apart from the crowd, both personally and professionally.

Of course, the reality is that high-level executives face some unique challenges when it comes to dating. For one, your time is limited. The last thing you want to do is to waste time on people who aren’t a good fit. But another challenge, one that’s rarely addressed, is power dynamics. When you’re successful, it can be tricky to figure out who is genuinely interested in you as a person versus who might see you as a stepping stone for their own goals, and this is where trust becomes critical. [13:47.8]

It’s important to get a sense early on of someone else’s values and intentions, and that requires a lot of emotional intelligence and good and healthy boundaries, so you’ll have to listen extra closely to what they say and, more importantly, how they say it. Are they overly interested in your career or your connections, or your resources? Do they seem more excited about your title than your stories of vulnerability? These are all subtle red flags that can save you a lot of frustration if caught early.

On the flip side, don’t let your success make you overly guarded. Not everyone is out to take advantage of you. But you should have a strategy for filtering people quickly and effectively, and this is where aligning dating with your ideal lifestyle can really pay off. The more you meet people in environments you already love, whether that’s a hiking group or a local art gallery, or a private event, the easier it will be to connect with those who are naturally aligned with who you already are.

Now, if you’re thinking, This sounds like it could get really overwhelming, then let me simplify it for you. The key to modern dating for busy professionals is to tailor the process to fit your life. Forget trying to force yourself into dating apps if they don’t work for you. Forget going on endless coffee dates that drain your time and energy. Instead, focus on creating opportunities to meet people in ways that feel natural, enjoyable and authentic. [15:16.0]

When you approach dating this way, two things can happen. First, it becomes easier. You’re not chasing. Instead, you’re creating space for connection in a way that aligns with your values and lifestyle. Second, the connections you make tend to be higher quality because you’re not relying on algorithms or random chance. You’re meeting people in environments where you’re already showing up as your natural self.

The takeaway is this: dating doesn’t have to feel like a second job. By understanding the dynamics of modern dating and then tailoring the process to your world, to your ideal lifestyle, you can simplify and enhance the experience. Maybe the best part is you’ll already be spending your time in ways that enrich your life, whether or not you meet someone right away. [16:02.7]

Now, let’s get to the third and final point, something that might make those who are used to living in their heads, in logic and cognition, maybe a little bit uncomfortable, but it’s absolutely critical when it comes to creating deep, meaningful connections, and this is emotional intelligence. If you’re a high-achieving professional, odds are you’ve mastered logic, strategy, execution, and that’s your comfort zone, but emotions and relationships, they don’t follow the same rules. Relationships are built on vulnerability, empathy and emotional depth, and these are muscles that don’t get much exercise in the corporate world.

So, here’s the challenge: the qualities that make you successful at work, like decisiveness, control and efficiency, can often work against you in your personal life and especially in your intimate relationships. In intimate relationships, people don’t want to be managed or solved. They want to feel seen, heard, understood, and that requires something that might feel unfamiliar at first, which is emotional awareness. [17:06.5]

You can start by cultivating self-awareness. This means taking a closer look at your own emotional landscape, what you’re feeling, why you’re feeling it, and how these feelings show up in your interactions with others. Most people skip this step, but it’s the foundation of emotional intelligence. If you’re not in tune with your own emotions, it’s almost impossible to connect deeply with someone else’s.

One of the most effective ways to build self-awareness is by reflecting on your past relationships. You can ask yourself, “What patterns do I notice here? Were there moments when I avoided vulnerability? Did I shut down emotionally when things got tough? How did that happen? How did I do it?” These aren’t easy questions to sit with, but they’re essential. The more you understand your own emotional tendencies and patterns, the better equipped you’ll be to break any unhealthy patterns and create healthier ones. [18:01.0]

Now let’s get into empathy. Empathy is your ability to step into someone else’s emotional world, to feel what they’re feeling, or at least attempt to. For a lot of executives, this might feel unnatural at first. When you’re used to solving problems and making decisions quickly, slowing down to really listen to their emotions can feel inefficient, but intimate relationships aren’t about efficiency. They’re about connection. They’re about the experience itself.

A simple way to practice empathy is by listening differently. Most of us listen with the intention of responding. Maybe we’re already thinking about what we’re going to say next before the other person has even finished talking. Instead, try listening with the sole intention of understanding, to feel what they’re feeling as they’re saying it, and, of course, to understand the content of what they’re saying. Pause before you respond. Ask clarifying questions first. Then reflect back what you’re hearing to make sure that you have understood, that you’ve got it. [19:00.7]

These small shifts can act like speed bumps to make sure that you stay present. This will change how you listen and transform the way people experience you, and will create the kind of trust and intimacy that is required for real connection.

But empathy alone isn’t even enough to build meaningful relationships, you also need strong communication skills—and, no, I don’t mean being persuasive or articulate, or presenting at a boardroom. I’m talking about communicating your emotions clearly and authentically, even when it feels or especially when it feels uncomfortable. Vulnerability doesn’t come easily for most high-achievers. It can feel risky, like you’re exposing yourself to negative judgment or rejection. But vulnerability isn’t a weakness. It’s a bridge. It invites the other person to meet you where you authentically are, to invite them to see the real you, not just the polished professional façade of you, but the human version. [20:00.2]

Okay, here’s an example. Let’s say you’re on a date and the conversation turns to past relationships. Here you have two options. You’re at a choice point. You can keep things surface-level, sharing just enough to seem polite and avoid anything messy, or you can take a better approach—you can share honestly about what you learned from those experiences, what challenged you, how you grew, and what you’re looking for now. The second option might feel riskier, but it’s also the only one that creates real connection. It shows also that you’re not afraid to show up as yourself, perceived flaws and all, and that is magnetic.

Now, I know some of you might be thinking, But I don’t want to come off as overly emotional, and you’re right. Don’t just start bawling right there on the first date. There’s a balance to strike here. Emotional intelligence isn’t about oversharing. It isn’t about getting lost in your feelings. It isn’t about requiring the other person to make you feel better. Instead, emotional intelligence is about integrating your emotional world with your logical one. It’s about showing up as a whole person. [21:09.0]

One of the most powerful ways to balance ambition with intimacy is to practice relational presence. This means being fully present with the person in front of you, rather than distracted by work or your phone, or your own thoughts. It sounds simple, but it’s incredibly rare, especially for busy professionals.

Real presence communicates care. It says, “I’m here with you and I value this moment with you,” and that kind of attention is what makes people feel deeply connected to you. This emotional skill of presence is so important that in my Emotional Mastery program, I dedicate multiple months to just studying, training and mastering this skill of emotional presence. [21:52.5]

Finally, let’s address a common fear, the idea that investing in a relationship might take away from your professional success. Here’s what I’ll say, when you create authentic connections, they don’t compete with your ambition. They complement it. A strong, fulfilling relationship doesn’t drain your energy. It replenishes it. It gives you a sense of grounding and purpose that carries over into everything you do.

In fact, I’ve dedicated multiple episodes of this podcast to unpacking the research findings from the longest running study in human history. That’s from the Harvard University Study of Adult Development, which has shown that the greatest single predictor of a long and happy life is the quality of your intimate relationships. In fact, for men, a good relationship can elongate your life by up to 12 years. So, emotional intelligence isn’t just a nice-to-have in relationships. It’s the foundation for creating connections that matter, and like any skill, it can be learned, honed, trained and mastered. It starts with self-awareness, grows with empathy and communication, and comes alive through presence and vulnerability. [23:00.6]

All right, we’ve covered a lot so far: rebuilding your identity, understanding modern dating dynamics, and developing emotional intelligence. Doing this kind of inner work on your own can feel overwhelming, and let’s face it, most of us don’t have the time to experiment for months or years trying to figure it out. That’s where having the right guide can completely shift your trajectory.

Let me share a story about one of my clients. Let’s call him Ethan. Ethan is a partner at a top firm, brilliant strategist and a guy who thrived under pressure, but when his five-year marriage ended, he felt completely lost. Suddenly, the same skills that made him a force to be reckoned with at work weren’t helping him pick up the pieces in his personal life. He came to me frustrated, exhausted, and frankly, skeptical that therapy or coaching could actually make a difference. [23:50.0]

When we started working together, we focused first on what Ethan had been avoiding, which was himself. He realized he’d spent years burying his emotions under achievements. His entire sense of self-worth was tied to his external success, leaving him disconnected from his authentic self. Through a mix of therapeutic coaching and approaches, like the Internal Family Systems, IFS therapy approach, Ethan began to unpack those layers. He discovered parts of himself that he’d been neglecting, his playful part, his creative part, even his desire for intimacy beyond mere physical connection.

Then we tackled the dating world for him. Like many busy professionals, Ethan thought dating apps were his only option, but after a few frustrating months, he realized swiping wasn’t for him, so we worked on integrating dating into his existing lifestyle. He started attending small gatherings at the private club he loved, hosting dinners where friends brought along other singles, and even initiating conversations in environments that he already enjoyed, like the wine tastings he goes to almost every week and the art gallery openings and events that he goes to. [24:56.7]

Slowly but surely, he found his new stride. The real transformation for him, though, came when we focused on emotional intelligence. Ethan had spent years avoiding vulnerability, but as he began practicing deeper empathy and honest communication, something shifted. His dates stopped feeling transactional and started feeling real. He connected with people, not as the successful partner of a big firm, but as Ethan, a man with his own story, struggles and desires.

Fast forward to now and Ethan’s in a relationship that he describes as the most fulfilling he has ever experienced. He’s still crushing it at work, but now he’s grounded in a way that enhances everything else he does, and he’ll tell you himself, he didn’t get there by chance. He got there by doing the inner work and having an expert professional guide him through it.

This kind of transformation is possible for anyone willing to put in the effort. But the reality is, growth like this doesn’t happen overnight, and it’s tough to do alone. Private therapeutic coaching accelerates this process. It gives you the structure, the tools and the personalized guidance to make real, lasting changes, and to make the most of this new chapter in your life. [26:08.3]

If Ethan’s story resonates with you and you’re ready to dive deeper and create the life and relationships you truly want, then it starts with one decision: to invest in yourself.

All right, let’s recap what we’ve covered today.

First, we talked about rebuilding your identity and confidence after a breakup or divorce. The key to this is reconnecting with your authentic core self, not just the version of you that crushes it at work, but the core person, the core you underneath it all. It’s about getting clear on your values, your passions and your non-negotiables, so you can build a stronger foundation for your future.

Next, we dove into understanding modern dating dynamics. If dating apps feel off, that’s totally okay. There are smarter ways to meet people, like integrating dating into the lifestyle that you already love, whether that’s through social mixers, curated dinner parties or natural conversations in the places that you enjoy most. [27:00.1]

Finally, we explored emotional intelligence. Vulnerability, empathy and presence aren’t optional. They’re at the core of creating meaningful connections. When you show up authentically, people feel it, and that’s what builds trust, intimacy and relationships that last. This is your path forward.

Thank you so much for listening. If you liked it, hit a like or give it a good rating on whatever platform you’re listening to this on. If this has helped you in any way, please share it with anyone else that you think could benefit from it, and let me know what you thought. Leave a comment or send me a message. I’d love to hear your feedback.

Thank you so much again for listening. I look forward to welcoming you to the next episode. Until then, David Tian, signing out. [27:38.2]