Modern Dating: Dating Apps, Attachment Styles & Life After Divorce

Fernanda: Hey friends, welcome back to the Connectedness podcast, the space where we get honest about love, connection, and what it really takes to grow a relationship.

Today I'm joined by my friend Chris, who brings such an interesting and thoughtful perspective to the table. Chris is divorced, back out in the dating world, and has a lot of insight into what it's like to navigate modern dating today—especially as someone who is emotionally intelligent, self-aware, and genuinely ready for something real.

This conversation isn't about blaming or bashing anyone. It's about exploring what is actually happening in the dating scene right now, why it feels so complicated, and what we can learn from it. We'll talk about what it means to "do the work" when it comes to personal growth, how that shows up in relationships, and what both men and women might need to understand about each other a little better.

Welcome, Chris! Thank you so much for joining me. Tell us a little bit about your story and what it has been like re-entering the dating world after divorce.

Chris: Thanks, Fernanda. It's always great catching up with you, so this is going to be a fun time.

I was married for almost 26 years and got divorced about a year and a half ago. Heading into that, not knowing what dating looks like after 25 years was definitely intimidating at first.

I really like what you said about it not being a blame game. When a date doesn't work out, I like to ask myself: "What did I learn about myself?" There are also great things you pick up from people that help shape and inform you.

Some of it is a bit of a horror show, but at the end of the day, people really want the same thing. If you ask anyone what they want, they say, "I want my person." It’s how we get there and how we show up that makes the difference in whether we find them.

Fernanda: It feels like a jungle out there right now, with social media, isolation, and everything working against real connection. After 26 years away from dating, what surprised you the most when you started dating again?

Chris: Looking back, you can move a little bit quicker in terms of communication. In our younger years, it was almost a kid's game of dancing around each other.

Now, you can just be more open: "Hey, I like to do X and Y, here's who I am." You can have honest conversations, and if things don't work out, you just move along. That directness was refreshing and surprising.

Fernanda: Has your approach to dating changed compared to when you were younger?

Chris: Back then, there were no dating apps. Also, the younger me probably would have been more intimidated to approach someone or make a move.

The current me has no problem going up and talking to anyone about anything, whether I want to date them or not. Stepping into it with confidence helps, especially knowing that if there's a rejection, it's not a reflection of my worth. It just didn't work out, and you move on.

Fernanda: Dealing with rejection comes up constantly in discussions about dating. A lot of people seem so uncomfortable with rejection that they don't put themselves out there at all, which becomes a vicious cycle.

Chris: When you care about someone and a connection ends, it still hurts. But it's about how you process it: What did you take away? What did you contribute, and did it reveal a blind spot you still need to work on?

You can take a moment to lick your wounds and then move forward. There's this belief that after a breakup you have to wait until you are 100% healed, but nobody is ever fully healed. It’s about what you learned, how you carry yourself into the next relationship, and the boundaries you uphold around what you will and won't accept.

Fernanda: Some people believe you have to wait six months or a year, while others take a decade before putting themselves out there again. Waiting ten years can mean missing prime years of life where you could have been having fun, connecting, and growing.

Chris: Everything you go through offers a lesson, and you are accountable for improving in the present moment. For people who have waited that long because of deep trauma, I hope they seek therapy and do the self-work, because otherwise, they're never going to be ready to be a healthy partner for someone.

Fernanda: From your perspective, what has shifted in how people connect online, and how are you navigating dating apps?

Chris: Online dating is essentially a marketplace full of swiping. The biggest aggravation point for men is the tedious messaging game: "Hi, how are you? How's the weather?"

It has become a speed culture of swipe, match, go on a date, fail fast, and repeat. Everyone does that because easy access back to the app is always right there.

I was fortunate to date people who understood the value of embracing the 80% that matches their core values and working through the remaining 20%. Instead, many people throw the whole connection away and spin their wheels looking for someone new, only to end up with a 40% match next time. We need to ask ourselves: when the initial mask falls, is the situation truly horrible, or is it something two people can work through?

Fernanda: It comes down to the myth of infinite options. People assume that because they're on an app, options are endless, which makes everyone feel disposable.

Chris: When people browse profiles, they look at physical attraction first, and many never even bother to read the bio. They discard anyone who doesn't fit a specific physical mold, so the entire dating pool ends up fighting over the exact same tiny percentage of people.

That creates a finite, competitive dynamic driven by inflated egos on both sides. People have to take a realistic look at whether they are actually bringing to the table what they're demanding from others.

Fernanda: It's like two Jenga towers where the bottom 90% are all staring up at the top 10%. Dating coach Sabrina Zohar talks about becoming a better shopper: being more realistic with your expectations and reasonable with your criteria.

Chris: I filter hard now. I don't just chase a pretty face or generic words, and I'm happy to pass on profiles that don't align.

My apps are mostly empty, and I'm completely fine with that. It allows me to focus on myself so that when the right person comes along, I'm ready, rather than chasing someone just to have a warm body around.

Fernanda: Do you find that people are more guarded, distracted, or simply unsure of what they want?

Chris: It's a mix of everything. People say they want to build something long-term, but they behave in ways that keep things purely surface-level and casual.

There's also a lot of unresolved baggage from past relationships. When I ask dates what they learned from their exes, and they say, "Not to date people like that," that isn't personal growth.

I want to hear: "I realized I picked that person because of my own insecurities, and here's what I did to heal that." That shows an evolved person who takes ownership.

People also have their guards up and play games around being chased. I tell women, "I will pursue you, but if you run away because you're avoidant, I'm not going to chase you, because then it becomes a game." We need to have open conversations about mutual respect, needs, and consistency.

Fernanda: How would you describe an avoidant attachment style?

Chris: It stems from not feeling your own worth and being scarred so heavily by past hurt that you're terrified to open up. People self-sabotage and ruin good things because they fear commitment or genuine closeness.

Fernanda: Would you consider yourself securely attached now?

Chris: I'm generally securely attached, though I can have a slight anxious tendency that I continue to work on. Being secure means I'm willing to walk away when a dynamic isn't healthy, or remain patient and calm to talk through each other's needs.

My non-negotiables are appreciation, respect, trust, and words aligning with actions consistently. If those don't show up, I step away.

I provide a safe, clear container for a partner, and I expect mutual consistency in return. Without those foundations, trust and safety cannot grow.

Fernanda: Do you find that dating is harder when you're an emotionally aware person?

Chris: I have struggled with that. A friend once asked why I have to be so intense about boundaries, but they matter because I've done the deep work, and I want someone who can meet me at that level.

These aren't impossibly high standards; they are basic emotional minimums. When you have emotional safety, conversations flow, fun happens, and true mental, emotional, and physical connection develops.

When you feel safe with someone, you stop overthinking and get to experience genuine intimacy and growth. I'm not interested in dating just for casual distraction—I have plenty of hobbies and passions for that. I'm holding out for my person.

Fernanda: What do you wish women understood about men who are genuinely trying to connect?

Chris: We are not your exes. Most men are trying to show up as their best selves, just like you are.

Many men struggle with showing emotion because someone in their past weaponized vulnerability against them, so it takes creating a safe space for them to open up. We also aren't mind readers, and we dislike guessing games.

If something bothers you, express it kindly using the feeling-behavior-impact framework: "When you did X, I felt Y." That gives us clear communication instead of passive hints. There are bad actors out there, of course, but the good men are doing their best to show up properly.

Fernanda: On the flip side, what have you learned that men could do better?

Chris: First and foremost: listen and communicate effectively. Men need to drop the mentality of wondering if they're going to get lucky, and focus instead on actually getting to know the human being in front of them.

I was surprised to discover how many women truly appreciate a grounded man who takes the initiative and leads. Many women are carrying heavy mental loads—especially single moms—and they appreciate a man who steps up, plans dinner, opens the car door, and offers steady protection without being arrogant or controlling.

Showing up as a dependable, respectful presence allows a woman's walls to come down naturally. But it has to be authentic consistency, not an act.

Fernanda: Being a gentleman and making someone laugh trumps superficial looks every time. The problem is you can't easily see charm or humor while swiping on an app.

Chris: In real life, you immediately feel someone's energy and vibe, which makes connecting feel much more organic. The hard part is that everyone is busy, so meeting people out in the wild happens less often than it used to.

Fernanda: Earlier you mentioned looking for someone who has "done the work." What does that mean to you?

Chris: It means taking ownership rather than playing the victim or blaming everyone else for your problems. You can tell through conversation whether someone has learned from their experiences, developed self-awareness, and cultivated a healthy community of friends.

I used to fall into the trap of dating potential—ignoring obvious red flags because I saw the good soul underneath. Now, I look for demonstrated actions: consistency, regular communication, and emotional stability.

Someone who has done the work doesn't treat interactions like a guessing game.

Fernanda: Doing the work creates self-compassion, and when you have self-compassion, you naturally stop being critical or judgmental toward others. You can tell a lot about a person by how they treat others, how they talk about themselves, and how they interact with service staff.

Chris: That self-compassion also changes how you handle conflict. In the past, I assumed an argument meant the end of the relationship, but healthy people see disagreement as an invitation for calm, curious conversation.

A mature partner reserves judgment, stays curious, and asks, "Tell me more about how you see this," rather than jumping to conclusions. Pairing that with a good sense of humor makes navigating life together so much easier.

Fernanda: What growth practices have shaped how you show up in your relationships?

Chris: I explored what I call my "woo-woo path" a few years ago: energy healing, Reiki, meditation, and life coaching. Those practices helped me understand the internal blocks we carry and taught me to focus on what is within my control while letting go of what isn't.

I've also focused on the concept of the divine masculine: stepping into a grounded, supportive role that provides a safe container for a partner to rest in her feminine energy. Feminine energy isn't about traditional domestic roles; it's about honoring intuition, creativity, and flow, while the masculine provides strength, safety, and direction.

Doing that work taught me to understand my past relationship choices, forgive them, and build daily habits that keep me grounded in my values. I know I still have blind spots, and I welcome a caring partner who can gently point them out so we can grow together.

Fernanda: Can two people grow together, or do they both need to be fully solid on their own first?

Chris: It's both. Each person needs to be secure and healthy individually, but nobody is ever 100% healed.

When two emotionally healthy people come together, they create a partnership where both can evolve. If one person continues to grow while the other remains stagnant, a painful disconnect eventually develops. Growth has to be mutual.

Fernanda: Frank and I have been together for fifteen years, and relationships can be hard specifically because they challenge us to grow. Even a happy partnership involves navigating bumps in the road together.

Chris: I love the mentality of waking up every day and saying, "I still choose you." Even during frustrating weeks, acknowledging that you still choose your partner honors the relationship and moves you past superficial dating habits.

Fernanda: What gives you hope about love and connection right now?

Chris: I believe my person is out there, and I enjoy the journey and the people I meet along the way. I'm cautious about who I let into my life, but I appreciate the shared moments, the lessons, and the personal growth each interaction brings.

In the meantime, I focus on my work, my hobbies, my workouts, and my friendships. I also stay heavily involved in F3, which is a free men's workout and leadership group that supported me immensely through my divorce.

Having that brotherhood keeps me grounded, and even when I find a partner, those friendships remain essential. Both partners need their own independent support systems so they aren't relying on one person to meet every single need.

Fernanda: Having your own lives and friendships outside of the relationship makes the partnership so much healthier.

Thank you so much, Chris, for your honesty and perspective today. Dating isn't just about finding the right person—it's about becoming the right person, too.

To everyone listening, remember to keep your heart open, stay grounded, and keep doing the work. Until next time, take care and keep your cups filled!