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.
The Question
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
The Answer
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.
RELATED: Signs She Actually Likes You & Isn’t Just Being Polite
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.
RELATED: How to Show You’re Interested Without Crossing Boundaries
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.
RELATED: Mistakes Guys Make in the First Few Dates
Here are the 6 Icks.
1: The Sex Object Ick
Leading with sexual comments that reduce her to body parts, rather than seeing her as a person.
The guy who walks up to a woman, looks at her chest, and oozes, “You look good” like he’s judging livestock at a county fair.
2: The Too Timid Ick
Bringing hesitant, unsure energy instead of calm confidence.
The guy at the bar who just stares at her but never says a word, making her feel watched.
3: The Me-First Ick
Focusing on what you want — attention, validation, sex — instead of creating a genuine, win-win connection together.
The guy who’s only focused on doing what it takes to get her into bed, treating the interaction like a transaction.
4: The Try-Hard Ick
Working desperately to impress her with false confidence, fake niceness, or bragging… instead of showing up as your real, grounded self.
The guy who brags (about his Mercedes, his status, his “second house in Miami”), shallowly seeking to impress.
5: The Signal-Blind Ick
Missing or ignoring social cues (such as her vibe, body language, the social context) and escalating when the time is clearly not right.
The guy who can’t read the room, leaving his hand on her thigh because he saw a reel about “breaking the touch barrier” — even though she’s recoiling.
6: The Agenda Ick
Using manipulative, high-pressure “seduction” tactics that ignore her boundaries and desperately steer the interaction toward an outcome she’s uncomfortable with.
The “pickup guy” who sees women as pretty pawns in a game of seduction chess, who pressures her for “one quick drink at my place” after she said she has an early morning.
The great news for good guys? Apart from long, timid stares, the men who fear being creepy rarely give women these icky feelings.
RELATED: 5 Types of Men Women Find Attractive
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:
Instead of treating a woman like a sex object, find out what makes her interesting and charming beyond her looks. Instead of yielding to timidity, fully commit to the approach or the move; a clear “hello” is always better than hovering.Instead of making it about what you want, focus on creating a win-win vibe that you and she both enjoy.Instead of trying hard to be impressive, be expressive, vulnerable, and always authentic. Instead of being blind to her cues, read them — if she opens up, move forward; if she closes off, ease back.Instead of pushing your agenda, lead the dance together, noticing how she’s feeling with you.
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.
You Might Also Dig:
Do Women Actually Want Good Guys?Why Do Women Ghost Me as Soon as We Start Talking?Should I Get Penis Enlargement Surgery?
The Question
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
The Answer
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.
RELATED: Signs She Actually Likes You & Isn’t Just Being Polite
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.
RELATED: How to Show You’re Interested Without Crossing Boundaries
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.
RELATED: Mistakes Guys Make in the First Few Dates
Here are the 6 Icks.
1: The Sex Object Ick
Leading with sexual comments that reduce her to body parts, rather than seeing her as a person.
The guy who walks up to a woman, looks at her chest, and oozes, “You look good” like he’s judging livestock at a county fair.
2: The Too Timid Ick
Bringing hesitant, unsure energy instead of calm confidence.
The guy at the bar who just stares at her but never says a word, making her feel watched.
3: The Me-First Ick
Focusing on what you want — attention, validation, sex — instead of creating a genuine, win-win connection together.
The guy who’s only focused on doing what it takes to get her into bed, treating the interaction like a transaction.
4: The Try-Hard Ick
Working desperately to impress her with false confidence, fake niceness, or bragging… instead of showing up as your real, grounded self.
The guy who brags (about his Mercedes, his status, his “second house in Miami”), shallowly seeking to impress.
5: The Signal-Blind Ick
Missing or ignoring social cues (such as her vibe, body language, the social context) and escalating when the time is clearly not right.
The guy who can’t read the room, leaving his hand on her thigh because he saw a reel about “breaking the touch barrier” — even though she’s recoiling.
6: The Agenda Ick
Using manipulative, high-pressure “seduction” tactics that ignore her boundaries and desperately steer the interaction toward an outcome she’s uncomfortable with.
The “pickup guy” who sees women as pretty pawns in a game of seduction chess, who pressures her for “one quick drink at my place” after she said she has an early morning.
The great news for good guys? Apart from long, timid stares, the men who fear being creepy rarely give women these icky feelings.
RELATED: 5 Types of Men Women Find Attractive
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:
Instead of treating a woman like a sex object, find out what makes her interesting and charming beyond her looks. Instead of yielding to timidity, fully commit to the approach or the move; a clear “hello” is always better than hovering.Instead of making it about what you want, focus on creating a win-win vibe that you and she both enjoy.Instead of trying hard to be impressive, be expressive, vulnerable, and always authentic. Instead of being blind to her cues, read them — if she opens up, move forward; if she closes off, ease back.Instead of pushing your agenda, lead the dance together, noticing how she’s feeling with you.
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.
You Might Also Dig:
Do Women Actually Want Good Guys?Why Do Women Ghost Me as Soon as We Start Talking?Should I Get Penis Enlargement Surgery?