Hey, Connell. I need some dating help! I am almost 30, and not only have I never had a girlfriend, I’ve never even kissed a girl. But I'm not sure what to do, or what steps to take first. And sometimes I feel embarrassed about even needing to ask for dating help. What do you think? What tips would you give a total newbie like me?
—David, 29, Ontario
Hey, David! First off, I’m glad you’re reaching out. Too many guys struggle in silence, thinking they have to figure everything out on their own. But dating isn’t some secret code you have to crack—it’s a skill you can learn, just like playing guitar or hitting the gym. And the great news? You’re not behind. You’re just getting started.
Here’s the first thing to know: women don’t care about your “stats”—how many dates you’ve had, whether you’ve kissed someone, or if you’re “experienced.” What they care about is how you make them feel. And that starts with authenticity.
Here’s the truth I tell men who come to me for dating help: Authenticity is your superpower. You don’t need cheesy pickup lines or to act like some “alpha” bro. The most attractive thing you can do is be the real, unfiltered you—the guy your close friends love, the one who’s funny, kind, and has interests he’s passionate about. When you show up as that guy, the right women will be drawn to you.
1. Get comfortable talking to women. No pressure, no expectations, just conversations. Strike up chats with baristas, coworkers, or even strangers in line at the grocery store. The goal isn’t to get a number—it’s to practice being social and playful so you feel at ease around women.
2. Launch a dating profile. Dating apps are a great way to dip your toes in. Get portraits taken where you look relaxed and natural, and write a profile that highlights your real personality. Avoid clichés like “I love to travel” (who doesn’t?). Instead, share something unique about yourself. Example: “Best meal I ever had? A midnight taco stand in Mexico City.” That’s specific, engaging, and makes for a great conversation starter.
3. Take action despite fear – It’s okay to feel nervous. That’s normal! But don’t let fear stop you from making moves. That cute woman you see at the bookstore? Say hi. That great match on an app? Ask her out. Confidence isn’t about never feeling fear—it’s about acting in spite of it.
Finally, let go of embarrassment. There’s nothing weird about seeking dating help. If anything, it shows that you’re self-aware and ready to grow. And that’s attractive as hell.
You got this, David. Take the first step, and keep me posted on your progress!
Lately, it feels like the world is telling me that being a kind, respectful man isn’t enough. Donald Trump, who I hate, is dominating the news, Elon Musk is celebrated as a bold risk-taker, and the Manosphere preaches Red Pill dating tips. Being a loud, brash, hyper-masculine man seems “in.”
Meanwhile, I’m just a quiet, thoughtful, kind guy. I see women as equals to be treated with respect. But I’m starting to wonder if being a nice guy is holding me back in dating. Am I just too nice for women in today’s dating culture? Can a guy like me even compete?—Zach, 29, Chicago
I get it. With Trump shouting from the headlines, Musk flexing his billions, and the Manosphere celebrating “alpha males,” the world can seem like one big chest-bumping contest.
But the idea that women only want loud, brash, hyper-masculine men is about as accurate as using the Farmer’s Almanac to predict the weather.
Here’s the truth: Women LOVE nice guys. In fact, kindness is the No. 1 quality women value most in a male partner, according to a poll conducted by the health app Clue, which surveyed 64,000 women. Supportiveness, intelligence, and education also ranked in the top 5—qualities you likely already have.
You know what’s NOT on that list of ladies’ preferences? Being a loud, brash jerk.
So the Manosphere and Trump—the Red Pill and the Orange Menace—might appeal to loud, frustrated guys, but they’re clueless about what truly makes a man attractive to women.
Take it from a professional dating coach for guys: Women love a nice guy, if—and this is a big “if”—he believes in himself and his worth. When you combine your kindness with unshakable confidence, you become the kind of man women are drawn to.
Your kindness isn’t holding you back, Zach. It’s your self-doubt, which might be sending the wrong signals. Women can sense when a man questions his own worth—and that’s what turns them off.
The problem with the Manosphere and its Red Pill nonsense is that it’s built on an outdated, toxic idea of masculinity: that men have to dominate, conquer, and suppress their emotions to succeed. Spoiler alert! That’s not what modern women want. Sure, confidence and assertiveness are attractive in the right measures, but not when they come packaged with ego, aggression, and a MAGA hat.
Think of masculinity not as being the loudest guy in the room but as being the most grounded and authentic one. It’s about owning who you are—kindness, respect, and heart—and pairing it with a quiet, unshakable belief in yourself.
That’s what women want: a man who’s strong enough to be vulnerable, confident enough to be kind, and brave enough to show up as his true self.
Let me give you some hope. I coach guys just like you all the time—thoughtful, kind men who think they can’t compete with the “bad boys.” Once they learn how to channel their inner confidence and approach dating authentically, everything changes.
Women aren’t looking for caricatures of masculinity; they’re looking for connection with a man who has a lot to give. And a guy like you—nice, respectful, and self-assured—has everything it takes!
So yes, Zach, you can absolutely compete in today’s dating culture. In fact, you can win. But the first step is dropping the idea that “nice guys finish last.” They don’t. The men who fail to believe in themselves are the ones who finish last.
Now go out there, own your kindness, and show the world and women what a Radically Authentic man looks like. The right woman will love you for you.
I’m decent at getting first dates from using the apps. But after the first date, women stop responding. Or when I text them to ask them out again, they say they didn’t feel a connection. We seem to have good conversations, but nothing works. I guess I could flirt more or take more chances, but I just don’t want to come off as creepy. I want to be a gentleman. What am I doing wrong, and how can I make a better impression to get second dates—and eventually a girlfriend?
—Barry, 34, Boston
You need to make a stronger impact on dates. Take more risks. A good conversation is a nice start, but women like a man who puts a card or two on the table.
In other words, playing it safe on first dates is risky. And taking risks on first dates is actually safe—in that it’s a safe bet you’ll stand out to her and get yourself a second date.
Here’s how to be a first-date risk-taker to get women asking you out for date no. 2.
Barry, have you ever told a woman on a first date that she’s sexy? Doing this may feel scary, but there’s nothing creepy about it—as long as you don’t make it about her physical features. Find something special about her and tell her, while using the S-word! “You have such a sexy, feminine laugh—it’s contagious” or “Your mind is so sexy—I love how you think about things.”
This makes her feel special on a deeper level, without objectifying her. Flirty but thoughtful compliments create romantic tension and show her you see her as more than just a friend.
Just make sure your compliment is real and authentic. No faking it!
If a first date is going reasonably well, then either go for the first kiss—or at the very least look her in the eye, shoot a sly smile her way, and say, “I want to kiss you.” Women appreciate confidence, and even if you go in and she turns the cheek, you’ll get points for trying.
But you WILL lose out on romantic connections, not to mention some hot AF make-outs, if you want to kiss her but let fear stop you. This timidity comes off as unattractive to women. Believe me, I’ve been there—it’s better to try and miss than not try at all.
So on any first date that’s gone fairly well—she’s engaged in the conversation and there’s a nice positive vibe between you—go for a first kiss toward the end of the evening. Women want men who take risks.
Before the date is over, confidently say something like, “I’ve really enjoyed tonight, and I want to see you again. When are you free next?”
No, this is NOT needy, as long as you completely own your interest and intention. Women like decisive guys who go after what they want. And two of the sexiest words to women are “I want.” Tell her what you want: a second date.
Stop playing it safe, Barry. Take some risks, make a stronger impact, and you’ll turn first dates into second dates in no time.
Dating coach Connell Barrett helps men all over the world find the women of their dreams. Connell has appeared on The Today Show, Access Hollywood, and more. Book a free call with Connell here.
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I'm dating coach Connell Barrett. I help men build confidence and connect with women by being authentic!
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