Welcome to AskMen’s latest column, Dating Coach, a monthly exploration of the difficulties guys face when it comes to modern dating. We’ve got a real, actual dating coach in Connell Barrett walking guys like you through everything from the most basic of the basics to the most pro of the pro tips.
I’m a firefighter, and I’ve run into burning buildings without a thought. But with women, I always freeze up. I don’t want to bother them and be “that creepy guy.” I can’t even take a woman’s hand on a date, let alone say hello to someone at a coffee shop. I feel stuck. Any advice?
– Fighting Fire & Fear
Long before I was a dating coach, I was at a rooftop lounge one night when I spotted a stylish woman at a table with her friends. Summoning all my courage, I grabbed an empty chair and said hello.
Her eyes widened, she leaned forward, and she said, “My God! You came right up and talked to us! Do you know what you are?”
I thought, “Umm, a creep who’s bothering you?”
“You’re normal!” she declared, to my relief. She tilted her head toward a fellow sitting a couple of tables away. “See that guy? He’s been staring at us all night, and it’s creeping us out.”
I left the lounge with her phone number and a lesson: It’s not creepy to take a chance. What’s creepy is wanting to take a chance, not doing it, and just timidly staring instead.
That’s the paradox, Fighting Fire. You think saying hello is risky? No. Risky is carrying a hose into a burning house. Saying hello is… saying hello.
The things you think are risky (taking a woman’s hand on a date, saying hi at a coffee shop) are actually normal. Creepy is when you hover, stare, and radiate uncertainty while she feels your presence but has no idea what you want.
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And the fear of being That Guy is more widespread than ever. I hear it constantly from my clients. They watch TikTok and Instagram videos about “creepy encounters” — men approaching at the gym, the grocery store, the sidewalk. And nearly every clip reinforces the same message: Any initiative is a violation. So a lot of men now treat normal social gestures like a potential crime scene.
No wonder you feel frozen! Scroll enough TikTok and you’ll feel like making eye contact at Whole Foods is a felony.
So, what’s the difference between making an acceptable move and being creepy? Attunement. A flirty move is showing romantic interest in a light way while reading a woman’s response. If she likes it, keep going. If not, ease off. Creepy behavior is showing miscalibrated interest while ignoring her signals — and pushing when she’s clearly not interested. That’s obliviousness, not boldness.
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What creeps women out isn’t initiative. It’s when guys hover, push, or ignore signals. Women generally don’t complain about clear, calibrated moves. They complain about moves made with zero attunement to how she’s feeling.
And that creates a problem for good guys like you. You’re so worried about crossing a line that you freeze. Meanwhile, the self-centered guys who actually creep women out aren’t worried at all.
The topic of creepiness made me ask a question: What behaviors genuinely creep women out? What the heck gives women the Ick?
After 20 years of studying dating (and hearing hundreds of women describe their experiences) I found the list surprisingly short.
Most every creepy behavior falls into one of six categories. I call them the 6 Icks.
If you avoid these pitfalls, you’re in the clear to take calibrated chances and make the moves that many women want you to make.
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Here are the 6 Icks.
Leading with sexual comments that reduce her to body parts, rather than seeing her as a person.
Bringing hesitant, unsure energy instead of calm confidence.
Focusing on what you want — attention, validation, sex — instead of creating a genuine, win-win connection together.
Working desperately to impress her with false confidence, fake niceness, or bragging… instead of showing up as your real, grounded self.
Missing or ignoring social cues (such as her vibe, body language, the social context) and escalating when the time is clearly not right.
Using manipulative, high-pressure “seduction” tactics that ignore her boundaries and desperately steer the interaction toward an outcome she’s uncomfortable with.
The great news for good guys? Apart from long, timid stares, the men who fear being creepy rarely give women these icky feelings.
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The fact that you worry about bothering women shows that you’re not a creep. Rather, you like and respect women. You have empathy and integrity.
You know who doesn’t worry about creeping out women? Actual creeps! So good on you for even asking this question.
Now that you’re armed with the 6 Icks, you can confidently make the kinds of moves that women tend to like, such as:
You’re a firefighter. Your job carries real risks — backdrafts, weak floors, hidden heat pockets. You avoid them with skill and calm.
Dating isn’t life or death, but the principle is the same. Know the hazards, avoid them, and move forward with confidence.
You run into burning buildings. Taking her hand? That’s the easy part.
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