Dating Intelligently 4: Authentic Love, Trust, and Connection

Author(s): Scott Douglas Jacobsen

Publication (Outlet/Website): The Good Men Project

Publication Date (yyyy/mm/dd): 2025/09/13

Christopher Louis is a Los Angeles–based international dating and relationship coach and the founder of Dating Intelligence. As host of the Dating Intelligence Podcast, Louis draws on intuition and lived experience to guide clients toward authentic selves and meaningful romantic connections.

In this conversation, Scott Douglas Jacobsen speaks with Louis about the concept of dating with intention. Louis explains that intentional dating is purposeful, value-driven, and centred on building meaningful connections rather than casual encounters or superficial checklists. He emphasizes clarity of goals, setting realistic expectations, and aligning words with actions. Louis highlights the importance of self-worth, trust, communication, and flexibility, noting that rigidity can close off opportunities. Green flags include curiosity and reciprocity, while red flags involve manipulation and self-centeredness. Ultimately, dating with intention means showing up authentically, embracing discovery, and valuing the privilege of connection.

Scott Douglas Jacobsen: Okay. All right, today we are here once more with the fantastic Christopher Louis. We’re going to discuss dating with intention. When you first mentioned this to me, I was struck by how North American that phrase sounds. So, if you know the origin of it, what is the origin? If not, regardless—what exactly is it?

Christopher Louis: Well, hey Scott, how are you doing? Dating with intention is really about being purposeful. It’s a deliberate approach to finding a partner that involves understanding your own wants and needs. It’s also about making conscious choices about who you date and seeking meaningful connections, as well as prioritizing your values and compatibility.

Most people don’t have a plan when they date. Dating with intention means actively seeking a meaningful, long-term partnership rather than casual connections or just filling a void. Most people, when they’re ready to date, just put themselves out there. But do you actually have a purpose? Do you actually know your type? Otherwise, it might as well be casual dating.

Dating with intention is distinct from casual dating. Casual dating often involves meeting people without a clearly defined goal in mind—you might explore your options and see where things go, but there’s no deliberate reasoning behind it. By contrast, dating with intention means knowing your core values, having clarity about the kind of relationship you want, and approaching dating with that in mind.

Jacobsen: Now, if you were to gauge the people who come to you for professional advising on dating, what percentage have no idea why they’re even approaching you? They’re just approaching you to date, without any intention of understanding why or how to do it.

Louis: Right. I’d say the ones who are serious about coaching are usually the ones who want to get better at dating with intention. Otherwise, many people come in with struggles, saying, “I just don’t know why I’m failing in the dating space.” Many of them have non-negotiables or preferences—things like wanting a partner with certain habits, values, or even physical traits. But the core issue is that most of them don’t really know what they want in a relationship at a deeper level.

They might say they want marriage, a house, or a family, but that’s vague. You need to go deeper. I ask them, “What are your examples of dating with intention?” and most of them respond, “I don’t really know.” So I give them examples.

First, clarity of goals. Why do you want to date someone? When you date that person, what are your shared goals moving forward?

Second, set clear standards. Choose a partner who aligns with your expectations and values, not just surface traits.

Third, focus on meaningful connections. Build a deep, authentic connection—not just pass the time or fill a void. Many people don’t know how to build that deeper connection. Too often, it’s like they’re just exchanging résumés: “I want this, this, and this. This is who I am. I do this, this, and this.” But that’s not really forming a deeper bond.

Finally, make conscious choices. Instead of drifting into whatever comes along, be deliberate about who you date. Ensure potential partners match your long-term goals. For example, someone might say, “I want a partner who shares my values about family,” or “I want someone who supports my career ambitions.”

I want this, but it’s like, you know, let’s go deeper than that. Let’s make a deliberate choice about who to date—do they line up with your values? Do they line up with your goals? Do they line up with your communication style and the other things that actually matter? You can have all the extras—all the fluff—but that doesn’t mean they’ll truly match your deeper connection or align with your authentic choices.

Jacobsen: When people become intentional about their expectations, does this force them to have a more realistic view? Both about what they can realistically expect, and also what they can realistically give of themselves in a dating context?

Louis: That’s a good point. I’d say it’s a fine line. When you ask about becoming more realistic, it’s really about coming to terms with your values and needs versus just saying, “I want, I want, I want.” That’s not realistic. It has to be a two-way street. You must delve into what you and another person can genuinely share in the present moment. What are your realistic future goals?

For example, it’s not just saying, “I want someone with money,” or “I want this, I want that.” If the other person doesn’t align with you in meaningful ways, then let’s be realistic—that’s not going to work. Take children, for example. Statistically, the average number of children per family is about two. So if someone says they want four, that might be unrealistic unless both partners agree. Start with the reality, then see where things grow.

More importantly, focus on the foundation: find someone honest with you, who’s trustworthy, who communicates well, who has the same level of self-awareness, who respects boundaries, and who uses that self-awareness to guide choices.

Jacobsen: What about matching words to actions? People might set expectations and goals, discuss them with a partner, and then re-enter the dating world at 40, 50, or 60. How effective are people at aligning their words with their actions once they become more intentional?

Louis: When people become intentional, they really dial into it. They allow themselves to weed through the fluff. That’s where frameworks can help. You mentioned off the record earlier the “three-three-three rule.” The way I see it, by the third date, you should already have a clearer sense of who’s sitting across from you. By three weeks, you should have a stronger impression: “Yes, I like this person, and we’re on the same path.”

By three months, you should be ready to decide: “We’re in a relationship now. Let’s be boyfriend and girlfriend. Let’s move forward.” At that point, it’s about seeing whether your goals, your intentions, and your focus align.

But let’s be honest: sometimes by the third date, you already realize this person doesn’t line up with what you want. And that’s okay—that’s the point of dating with intention. It’s better to recognize that early.

Sometimes you meet someone who doesn’t align with your values. They don’t have a plan, and their goals don’t match yours. Maybe the person is cute, sexy, or attractive, but that alone doesn’t add up to what you want in the long run. You have to learn how to let that go. When you’re dating with intention, you’re able to let those mismatches go much earlier in the dating process.

Jacobsen: Is the philosophy of intentional dating, in a way, a counter to simply letting your future be guided by randomness—or outsourcing your future to randomness?

Louis: No, I wouldn’t put it that way. Dating with intention isn’t about eliminating randomness. Remember, dating is still about meeting people and finding someone who shares your values and goals. You’re looking for a partner who aligns with you. But life isn’t static. As time goes on, values can shift. What you want today might evolve in a year. Sometimes your partner’s path may change, and you might see yourself moving in that direction because it adds value to the relationship.

In that sense, intention isn’t rigid. It flows. You adjust your intentions and alignments as life ebbs and flows. You do need some openness to randomness, because sometimes those unexpected turns are exactly what you need. Anyone who’s too rigid—with unmovable values or non-negotiables—can close themselves off. Flexibility is essential. Isn’t that the whole point of dating in the first place? Having some flexibility?

Jacobsen: What are the common questions people ask you about intentional dating?

Louis: The first question is almost always, “What does that even mean?” Then they ask, “How do I do that?”

My first response is: clarify your goals. What do you want? Write them down. Out of that list—say you write five or ten things—understand that no one will match all of them. But if someone matches three out of five, or six out of ten, that’s promising.

The next step is setting expectations. Do you want to build a deep emotional connection? Do you want someone who respects your boundaries and understands their own? Those questions matter.

Communication is huge here. Dating with intention—like any other kind of dating—boils down to effective communication. Are you able to communicate what you want, and are you able to listen in return?

And here’s something important: dating with intention doesn’t always mean you’re looking for something serious. Being intentional means being honest about where you are. For example, you might say, “I’m not looking for anything serious right now, but I like you.” That’s still dating with intention, because you’re being open and transparent.

For example, someone might say, “I’m really looking for a long-term partner. Is that what you’re looking for as well?” That’s still intentional dating. Yes, many people want to find a long-term partner, but some are also intentional about saying, “I just want to date right now casually—are you open to that?” And some people agree, because their lives are busy. They set the tone together: maybe they’ll see each other once every two weeks, but they’re still genuinely into each other. That can last until their goals or plans shift.

Jacobsen: Do people have to take into account new evidence—like when they start to feel strongly attracted to someone—that might change their goals? For example, they start developing a meaningful connection. They begin scheduling more time with that person, building interactions. At first, their intentions may have been vague, but they’re starting to hit some real notes of connection.

Louis: I see what you’re saying. Yes. Once again, here’s the key point—and you should include this in your writing: things will continually change. Start simple. Write down three to five goals. Set some expectations about what you want from a relationship. Define your communication boundaries. That’s the template.

Once you have that framework, everything else is about discovery. Ideally, you’re thinking, “Yes, this still fits what I want, but I’m also discovering something new along the way.” Someone who makes their list too long or too rigid isn’t really being intentional—they’re being unrealistic. They’re setting standards so high they’ll never find anyone to match them.

You need balance. Be intentional, but not rigid. That opens your dating pool and helps you find a partner who’s right for you, instead of closing off opportunities because of an overly strict checklist.

Jacobsen: In a way, does your work help clients grow by widening their horizons?

Louis: Yes. Many clients come in with tunnel vision. They’re very narrow-minded, locked into what they think they want. I’ll say to them, “Look, I hear you, I see what you’re asking for—but this perfect person you’ve imagined doesn’t exist. It’s nearly impossible to find someone who matches every single box.”

Matchmakers send clients to me all the time for this reason. Their lists are too long, full of non-negotiables, and no one could realistically meet them. My work helps clients open their eyes, broaden their perspective, and understand what really matters.

Some clients come in with lists that are far too demanding—physical traits, mental traits, lifestyle checkboxes—it’s just too much. The chance of finding someone who meets every single requirement is almost nonexistent. Honestly, you’d have better odds of winning the lottery. You have to widen your field of vision. Instead of hunting for that one mythical “golden unicorn,” think about finding a whole field—you’ll have more options, more matches to learn from, and a better chance of finding someone who actually fits you.

Jacobsen: If clients do show a willingness to change some of their expectations and goals, what actually matters in dating? And what do people think matters that, in the long run, turns out to be superficial?

Louis: Good question. I can’t speak for everyone, but in my experience, what matters most is simple: does the person make you happy? Do they make you feel safe? Can you trust them? For women in particular, that feeling of safety is critical. For both men and women, communication is essential. And yes, some level of attraction matters—maybe it’s their smile, perhaps something else—but it doesn’t need to be about strict physical stats or intellectual posturing.

What I tell everyone is: clear your mind and ask three questions. Does this person make me feel good? Does this person make me feel safe? And do I trust this person? Those are the three pillars.

Jacobsen: What makes men feel unsafe? What makes women feel unsafe?

Louis: For men, the big issue is usually ego. Trust is at the core. Many men struggle with jealousy. They might idealize a specific type of woman, but once they’re with her, they don’t trust her when she goes out. Their insecurity and ego get in the way of building absolute trust. That’s what makes them feel unsafe—when they can’t let go of that fear.

For women, what makes them feel unsafe is often arrogance. Men who lean too hard into narcissism or who project a hyper–alpha vibe without emotional intelligence create insecurity. Yes, many women are drawn to confidence and strength in a man, but that needs to be balanced with emotional awareness and empathy. Without that, “alpha” turns into controlling, and safety evaporates.

Jacobsen: He needs to be able to communicate with you. He needs to make—hmm. What are the triggers you’ve noticed in real dating contexts that activate a man’s ego or trust issues early in the dating process? And for women, what are the signals that a man’s pride crosses into arrogance or even narcissism—where traits that seemed like healthy confidence at first turn out to be something more toxic?

Louis: Right, I hear you. Let’s start with men. The big trigger is trust. Many men feel unsafe because they doubt whether they can trust the woman across from them. They might think, “If she looks this good with me, how can I trust her when she goes out? If she’s this fun and flirty with me, how do I know she won’t act the same with other guys?” That insecurity skews their sense of trust.

There’s also a double standard. A man may feel free to say, “Wow, she’s beautiful,” about another woman, but if his partner says the same thing about another man, he gets jealous, offended, or even threatened. That’s ego talking, and it undermines trust.

Now, for women, the trigger is often when early charm morphs into manipulation. Some men start charismatic—saying all the right things—but that can be a mask. Over time, those men may show signs of narcissism, arrogance, or untrustworthiness. The problem is that many women don’t catch the signals early, especially if they struggle with self-worth.

Predatory men can pick up on those insecurities. They exploit them—preying on weaknesses and presenting themselves as the solution: “You need me. I’ll make you better. I’ll take care of you.” At first, that looks like support, but it’s really control. Women often gloss over red flags because they interpret that behaviour as care, when it’s actually manipulation.

Jacobsen: That raises another important point—about people being preyed on at vulnerable moments in their lives. What are your top two warning signs, for men or women, that a man is preying on them in that way? What about the green flags, as a pivot from the discussion of the red flags?

Louis: The red flags I tell women to look out for—and men too, honestly—are when someone tells you exactly what you want to hear. That’s a significant warning sign. Another is when they talk constantly about themselves, about what they can do for you, how they’ll make you feel, or how they’ll improve your life. On the surface, it sounds flattering, but it’s self-centred. It’s all “I can, I will, I want to.”

Many women like to be doted on—that’s natural. They want to feel good, loved, and attractive. But the difference between a red flag and a green flag lies in whether the other person shows genuine interest in you. A green flag is when a man asks questions, listens, and shows curiosity about your life. If you ask him something, and he answers while also showing interest back in you—that’s healthy. If instead he only makes it about himself, that’s a problem.

Compliments like “You’re so pretty” or “You’re so hot, I just want to take care of you” sound nice, but if they’re not balanced with genuine curiosity about who you are, they’re actually red flags. An authentic green flag is reciprocity, mutual interest, and open communication.

Jacobsen: In the context of intentional dating, with a realistic assessment of self and others, is part of it just showing up authentically? For instance, when someone has built a little connection early on, they essentially come to the other person saying, nonverbally, “I’m just a person. I see you as you are. Let’s see if we fit.” Is that an accurate—if maybe oversimplified—assessment of the overall dynamic?

Louis: I hear you now, yes. I like how you put that. Dating intentionally starts with bringing your authentic self to the table. That means showing up with a few clear goals, some core values, and a few expectations. That’s all you need. But you also want openness—being present without turning the date into a presentation or a performance.

When people come in saying, “This is what I want: I want to be married in two years, I want two kids, I want a house, I want to be a stay-at-home mom, or I want a partner with a great job”—that can be too much. They’re putting pressure not only on the other person but also on the dating process itself. Even if they could have had an excellent long-term relationship with that person, they’ve buried it under heavy expectations.

It’s better to come in saying, “I’m just a person. I want to be present. I want to be intentional with you. Here are some things I’d love to talk about, so we can see if we share a long-term vision.” If things don’t match up, fine—at least you’ll know before wasting time. But that requires open communication: saying clearly, “These are the things I’m looking for. How do you feel about that?” Simple, straightforward, without a giant checklist.

If you come in with a literal list—step one, step two, 100 things you want from someone—that’s too rigid. That turns dating into a job interview, and nobody should treat a first date like that.

Jacobsen: So in a sense, it becomes like a job interview.

Louis: Exactly. And if someone comes in with what looks like a job description for their ideal partner, I’d say: entertain it for a bit, see if they can relax. Sometimes it’s nerves—it might be their first date in years, maybe they’re older, divorced, or widowed. They’ve been through relationships before, so they bring more intensity. And that’s okay—it makes sense that older daters want clarity and don’t want to waste time.

But for younger people, it’s different. If you’re 20 and on your first few dates, don’t come in with a whole life plan already mapped out. Ease into it. Learn through the process, communicate, and figure out what you want as you go.

Jacobsen: What about skills people are actually good at? They come to you thinking they’re weak in certain areas—such as setting expectations or goals—but in reality, they don’t need much work in those areas.

Louis: That’s a good one. But let me start with the opposite: the skills people actually do need to work on. Many people come in saying, “I’ve got the flirting down. I know how to communicate. I’m good at all that.” But here’s the real question: do you know your self-worth? Have you taken time to love yourself before trying to love someone else? That’s where many people stumble.

Too often, people enter dating hoping to become what someone else wants, rather than standing firmly in who they are. It’s a kind of imposter syndrome. They audition for the other person instead of remembering that the date is also an audition for them. I tell my clients: sit across from that person and think, “Are they auditioning for me? Do they fit into my life?” Not, “How can I mould myself into what they want?”

Otherwise, you end up six months into a relationship only to hear, “I only did that because I thought that’s what you wanted.” That’s heartbreaking, and it happens far too often.

Jacobsen: We’re almost out of time—about a minute left. Any final quotes? They could be from Oprah, or maybe one of the Williams sisters, since we’ve been using tennis as a theme.

Louis: Oh my gosh, yes. There’s actually a great Billie Jean King quote—it’s written at the U.S. Open. It says, “Pressure is a privilege.” It’s a reminder that if you’re feeling pressure, it means you’ve earned the right to be in that situation.

That applies beautifully to dating. A first date comes with stress and anxiety—of course it does. However, if you frame it as a privilege, you view the pressure differently. You’ve earned the right to sit across from someone and explore the possibility of a connection. The question is, can you rise to that moment? Can you manage the stress and still show up authentically? That’s what intentional dating is about.

When you are dating someone, there is a lot of pressure. Many people get anxious. Many people are stressed out. Quite frankly, some people who go on blind dates have no idea who the other person is or what they look like. They only have a profile in front of them. I tell my clients. “When you go on that first date, just be present, because pressure is a privilege. There is much pressure. You will put much pressure on yourself. ‘Is this person going to be the match for me? Are we going to match up? I am so excited. I want this person to be the one.’ Don’t put so much pressure on yourself. It is a privilege to be out and about. It is a privilege to go out on a date. Go through the process. Be present, be present in the moment. Enjoy the time that you have with that person.”

Jacobsen: Thank you for the opportunity and your time, Chris.

Louis: Thanks, Scott.

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