Let’s start with something that might sting a little.
You’re successful. You’ve built a career, crushed targets, and earned respect in your industry. You know how to close deals, lead teams, and solve complex problems under pressure. And yet… dating feels like a foreign language you somehow never learned.
You’ve swiped until your thumb went numb. You’ve been on dates that felt more like interviews. You’ve heard “you’re such a great guy, but…” more times than you’d care to admit. And honestly? You’re exhausted.
Here’s the thing: you’re not alone in this. Not even close.
As a dating coach for men, I work with driven, intelligent professionals every single day who are absolutely killing it in every area of life, except this one. And after years of conversations, coaching sessions, and watching patterns repeat themselves, I’ve noticed the same seven mistakes showing up over and over again.
The good news? Once you see these patterns, you can actually do something about them. So grab a coffee (or something stronger), and let’s get into it.
Mistake #1: Treating a Date Like a Business Meeting 📋
Picture this: You sit down across from her at a nice bar. You’re nervous, so you fall back on what you know. You start asking questions. Lots of them.
“So, what do you do for work?”
“How long have you lived in Sydney?”
“Do you have siblings?”
“What are your five-year goals?”
Before you know it, she feels like she’s in a job interview, and you’re the hiring manager with a clipboard.
Here’s the problem: connection doesn’t come from collecting information. It comes from creating a feeling. When you rapid-fire questions without sharing anything yourself, without playfulness, without letting the conversation breathe… it feels transactional. Clinical. Safe.
And safe, my friend, is boring.
What a dating coach would tell you: Slow down. Share stories. Make observations about what’s happening around you. Tease her a little. Let there be pauses. A date should feel like an adventure, not an audit.
The goal isn’t to learn her resume, it’s to make her feel something when she’s with you. That’s what she’ll remember later when she’s deciding whether to text you back.
Mistake #2: Prioritising Logic and Facts Over Emotional Connection
This one’s sneaky because it feels so… reasonable.
You think: “If I can just demonstrate my value, my job, my apartment, my hobbies, my travel experiences, she’ll logically conclude I’m a great catch.”
But dating doesn’t work like a pitch deck. She’s not evaluating your qualifications. She’s evaluating how she feels around you.
I once worked with a client, let’s call him Daniel, late 30s, finance executive, who couldn’t understand why his dates never led anywhere. On paper, he was doing everything right. Great conversation, nice restaurants, genuine interest in her life. (Details changed for privacy.)
But when we dug deeper, I noticed something: Daniel was so focused on being impressive that he forgot to be interesting. He talked about facts but never feelings. He described his life but never revealed his personality. There was no tension, no playfulness, no spark.
What a dating coach would tell you: Facts tell. Emotions sell. (Yeah, I borrowed that from marketing, but it applies here too.)
The best dating advice for men I can give you is this: she doesn’t need to know what you do, she needs to know who you are. What lights you up? What frustrates you? What makes you laugh until you can’t breathe? That vulnerability, that humanity, is what creates real connection.
Mistake #3: Neglecting Your “Personal Brand” (Style, Grooming, and Photos)
Hear me out before you roll your eyes.
I’m not talking about becoming someone you’re not. I’m talking about presenting the best, most authentic version of yourself, and doing it intentionally.
Think about it: you wouldn’t show up to a board meeting in a wrinkled shirt with bad lighting on your Zoom call, right? So why are your dating app photos a blurry bathroom selfie from 2019?
Your visual presentation matters. Not because you need to look like a model, but because how you present yourself communicates something about how you feel about yourself. And confidence, real, quiet confidence, is attractive.
This goes beyond photos, too. When’s the last time you updated your wardrobe? Got a haircut that actually suits your face shape? Thought about whether your style reflects the man you are now versus the one you were five years ago?
What a dating coach would tell you: A dating makeover isn’t about vanity, it’s about alignment. It’s about making sure the outside matches the incredible person on the inside.
At Dating by Richie, our 3-Day Dating Makeover intensive is specifically designed for busy professionals who want to transform their dating presence in a focused, structured way (without trying to become someone you’re not). We work on everything from your wardrobe and grooming to your dating profile, photos, and first-date energy. It’s a structured refresh.
Mistake #4: Being Too “Nice” (AKA Playing It Too Safe)
Okay, this one requires some nuance. Because being genuinely kind is a wonderful thing. The world needs more of it.
But there’s a difference between being kind and being a pushover. Between being respectful and being forgettable. Between being considerate and being… beige.
Here’s what I see all the time: Professional men who are so terrified of saying the wrong thing, of being “that guy,” of making her uncomfortable, that they strip away everything that makes them interesting. They agree with everything she says. They never challenge her. They never flirt. They never take a risk.
And then they’re shocked when they end up in the friend zone.
What a dating coach would tell you: Attraction requires polarity. It requires a little friction, a little tension, a little “I don’t know where this is going, but I want to find out.”
This doesn’t mean being rude or controversial for the sake of it. It means having opinions and sharing them. It means playfully disagreeing sometimes. It means not putting her on a pedestal, because pedestals are lonely, and nobody wants to date someone who worships them.
The most attractive thing you can do? Be authentically yourself, even if that means risking her not liking it. Because the right person will like it. And that’s the whole point.
Mistake #5: Over-Reliance on Dating Apps Without a Strategy
Raise your hand if this sounds familiar:
You download Hinge. You spend 20 minutes uploading photos and writing a bio you’re not thrilled with. You swipe whenever you’re bored. You send generic opening messages. You get a few matches, but most conversations fizzle. You delete the app in frustration. Two months later, you download it again and repeat the entire cycle.
Sound about right?
Here’s the truth: dating apps can work. But not the way most men use them.
Most guys start swiping, and it can start to feel like a slot machine—pull the lever, hope for a jackpot. But successful online dating requires intentionality. It requires a profile that actually stands out (and there’s a strategy to that). It requires openers that spark curiosity. It requires knowing how to move from chat to date efficiently without being pushy.
What a dating coach would tell you: Stop treating the apps like a lottery and start treating them like a skill you can develop. Because that’s exactly what they are.
A good dating service for professionals doesn’t just teach you what to say, it helps you understand why certain approaches work and how to adapt them to your personality. It’s not about scripts. It’s about a strategy that feels authentic to you.
If you’re curious about what a more intentional approach might look like, our free resources are a great place to start.
Mistake #6: Lack of Vulnerability and Emotional Intelligence
This is the big one. The mistake underneath all the other mistakes.
So many professional men have spent their careers learning to be competent, capable, and in control. You’ve been rewarded for having answers, for solving problems, for never showing weakness.
But here’s the uncomfortable truth: those same qualities that make you successful at work can make you terrible at intimacy.
Vulnerability isn’t weakness. It’s courage. It’s the willingness to be seen, really seen, even when there’s no guarantee of acceptance. And without it, you’ll always feel like something’s missing in your relationships. Because it will be.
Emotional intelligence matters too. Can you get better at noticing cues (and then checking in, rather than guessing)? Can you notice when you’re getting defensive and choose a different response? Can you sit with uncomfortable emotions instead of trying to fix them immediately?
What a dating coach would tell you: This is exactly where NLP (Neuro-Linguistic Programming)-informed coaching can be really useful. At Dating by Richie, I use NLP-informed tools to help you notice patterns—your communication habits, your triggers, your dating choices—and then practice new responses that feel more grounded and intentional.
Over time, that kind of work can make dating feel easier and more intentional.
Mistake #7: Thinking You Can “Solve” Dating Alone
And here’s where I’m going to be direct with you.
You wouldn’t try to get in the best shape of your life without a trainer. You wouldn’t scale your business without mentors and advisors. You’ve probably worked with coaches for your career, your health, maybe even your golf swing.
So why do you think dating, arguably one of the most complex, high-stakes areas of your life, is something you should just “figure out” on your own?
There’s this weird stigma around getting help with dating. Like it’s an admission of failure. Like “real men” should just naturally know how to do this.
But here’s what I’ve learned after years as a relationship coach: the men who tend to make progress sooner are the ones who invest in support. Not because they’re broken, but because they’re smart enough to know that outside perspective accelerates growth.
When you’re inside a problem, you can’t see it clearly. That’s just human nature. Having someone who can observe your patterns, challenge your blind spots, and hold you accountable? That’s not cheating. That’s wisdom.
What a dating coach would tell you: You’ve invested in every other area of your life. Why not this one?
So, What Now?
If you’ve made it this far, you’re already ahead of most guys. Because awareness is the first step. You can’t change what you can’t see.
But awareness alone doesn’t create results. Action does.
Here’s what I’d recommend:
- Pick one mistake from this list that hit hardest for you. Start there. Don’t try to overhaul everything at once.
- Get honest feedback. Ask a trusted friend (or better yet, a professional) to give you real talk about how you’re showing up in dating situations.
- Consider investing in yourself. Whether that’s our 3-Day Dating Makeover, personalised 1-on-1 coaching, or just booking a discovery call to chat about where you’re at, stop trying to figure this out alone.
At Dating by Richie, I work with busy professionals who don’t have time to waste on generic advice. Every coaching relationship is personalised to your specific situation, your specific patterns, and your specific goals. Plus, with 16/7 SMS support, you’ve got a coach in your corner even when you’re standing outside the restaurant wondering what to text.
This isn’t about becoming someone else. It’s about removing the obstacles between you and the connection you actually want.
The Bottom Line
Dating shouldn’t feel like a puzzle you can’t solve. You deserve to feel confident walking into a date. You deserve matches who actually excite you. You deserve relationships that feel easy, fun, and fulfilling.
The skills to get there? They’re completely learnable. And the right dating coach for men can show you how: faster than you’d ever figure out alone.
Disclaimer
Dating by Richie provides coaching and educational guidance only. We don’t provide medical, psychological, or mental health services, and coaching is not a substitute for therapy or professional advice. Any examples are for illustration (details may be changed for privacy). Results vary by person and depend on individual effort, circumstances, and compatibility.
Ready to stop making the same mistakes and start giving yourself the best chance at different results?
