Every week I get some version of the same message: “Maximo, I see women I’d like to talk to, but I’m terrified of being that guy.” The creepy guy. The one her friends laugh about later. The one she has to escape from. I respect that fear, because it means you care about how you make other people feel. That is already more than many men who approach women without a second thought.
So let’s talk honestly about how to approach a woman without being creepy. Not with a script, not with tricks, but with the same principles I see every day working around women who are approached constantly and who have very clear opinions about what feels good and what feels awful.
What “creepy” actually means
Creepy is not about how you look. I know men who are not conventionally handsome who approach women all the time and leave every interaction on good terms. I also know very attractive men who make women deeply uncomfortable.
The difference is pressure. A woman feels creeped out when she senses that a man:
- Will not take a hint.
- Has trapped her in a place she cannot easily leave.
- Wants something from her that she has not offered.
- Is watching her for too long before acting.
- Is getting physically too close too fast.
- Will react badly to a no.
Put simply: creepy is the feeling that saying no will be difficult or dangerous. Remove that feeling, and you remove almost all the creepiness. Everything else in this column comes from that one idea.
Choose the moment, not just the woman
The single biggest mistake I see is not a bad line. It is bad timing. A great approach at the wrong moment still feels like an intrusion.
Good moments usually have three things in common: she is relaxed, she is not in a hurry, and she can easily walk away. Think of a café where she is lingering over a coffee, a bookshop, a park, a social event, a gallery, a bar where people are clearly there to socialise, a party with mutual friends, a class or a hobby group after the session ends.
Moments to avoid:
- She is wearing headphones or clearly focused on something.
- She is working. Waitresses, baristas and shop staff are paid to be friendly and cannot leave.
- She is mid-workout at the gym.
- She is alone at night on a quiet street, on a train or in a car park.
- She is in a hurry, on the phone or dealing with a child.
If you are unsure, imagine how you would feel if your younger sister were approached in that exact moment. That instinct is usually right.
Do not hover
Many shy men stare for twenty minutes, building up courage, before finally walking over. By that point she has noticed you watching her, and the approach already feels heavy.
Watching is pressure. If you are going to say hello, do it within a minute or two of noticing her, or let it go. Short hesitation is fine. Prolonged surveillance is not.
Open simply and honestly
Forget clever openers. In my experience, the best ones are almost embarrassingly simple:
- “Hi, I’m Daniel. I saw you and wanted to come say hello.”
- “Excuse me, I have to ask, what are you reading? It looks good.”
- “This is my first time at this place. Is the food as good as people say?”
- “I don’t normally do this, but I thought I’d regret not saying hi.”
What makes these work is not the words. It is that they are honest, they are low stakes and they give her an easy way to answer or to politely end things. My column on how to talk to a woman you just met explains what to do once the conversation actually starts.
Body language: give her space
Stand at a slight angle rather than squarely in front of her. Keep a comfortable distance; an arm’s length is a good starting point. Never block her path to the exit, her friends or her drink. If she is sitting, you can ask if you can join briefly, but do not just pull up a chair.
Keep your hands visible and relaxed. Speak at a normal volume. Smile with your eyes, not just your mouth. And absolutely no touching in the opening moments, not even a “friendly” hand on her shoulder. If physical contact ever happens, let her initiate it first.
Watch her response in the first 30 seconds
You will usually know within half a minute whether she is open to talking. Signs she is warming up: she turns toward you, smiles genuinely, asks a question back, puts her phone away, gives longer answers.
Signs she is not: she keeps her body turned away, gives short answers, looks at her friends or phone, gives a tight smile and then looks elsewhere, or says she is waiting for someone.
If you see the second set, do not try harder. Wrap it up warmly: “Well, it was nice to meet you, enjoy your night.” Then leave. That clean exit is what separates the respectful man from the creepy one. I wrote much more about reading these cues in my column on the real signs a woman is interested.
Keep it short
A good approach is short. Two to five minutes is plenty for a first conversation with a stranger. If it goes well, the goal is not to stay for two hours. It is to create an opportunity to see her again.
Leaving while the conversation is still fun has two advantages. It shows you are not desperate, and it leaves her with a good feeling rather than a sense of being stuck. “I have to get back to my friends, but I’d love to continue this. Could I get your number?” is a natural way to close.
Asking for her number (and accepting the answer)
Ask directly and make it easy to decline: “I enjoyed talking to you. Would you like to swap numbers?” or “Can I take you for a coffee sometime?”
If she says yes, great. Take her number, say goodbye and leave. Do not linger for another half an hour. If she hesitates or says she has a boyfriend, accept it without question. Whether the boyfriend is real or not is none of your business. “No problem, it was nice to meet you” is the only correct response.
Some women will offer their Instagram instead of a number. That is also fine. Some will ask for yours instead. Respect that too; it gives her control, which is exactly why she asked.
What never to do
- Do not follow her, wait for her outside or approach her again after a no.
- Do not comment on her body. “You have a beautiful smile” is fine; anything sexual is not.
- Do not approach a group and single out one woman in a way that embarrasses her.
- Do not get angry or sarcastic when you are turned down.
- Do not take photos of her or film the interaction for social media. This is surprisingly common now, and it is disrespectful.
- Do not use alcohol as courage. One drink to relax is fine; a drunk approach is almost always creepy.
What working around women taught me
In my work, I spend a lot of time with women who are extremely confident and very used to male attention. Off camera, they are approached constantly, online and in real life. When I ask what makes an approach feel good versus horrible, the answers always come back to the same few things: be clear, be brief, be kind, and leave when asked.
What they hate most is not shyness. They often find shy men sweet. What they hate is a man who does not hear “no”, who argues, or who makes them feel trapped. That tells you something important: the bar is not “be smooth”. The bar is “be safe and be decent”. Almost any man can clear that bar.
Many of the women in my industry are also bold founders who built businesses by taking risks and approaching people others were afraid to talk to. One of my favourite examples is Joanna Angel, the Rutgers English major who built Burning Angel. And if you want to see the women I have worked with, visit fuckingpornstars.net.
How to build the courage
Approaching women is a skill, and skills come from practice in low-stakes situations. Start by talking to everyone: ask a stranger for a recommendation, compliment someone’s dog, chat to the person next to you in a queue. You are training your nervous system to understand that talking to strangers is safe.
Then set small goals. One hello this week. Two the next. Not “get a number”, just “say hello and leave politely”. Over a few weeks, the fear shrinks. Not to zero, but to something manageable.
And remember: most women are not offended by a respectful hello. Many are flattered, even if they are not interested. The fear in your head is usually far bigger than the reality.
Your seven-day plan
Day 1: Make small talk with three strangers, anyone at all. Day 2: Practise a simple opener out loud until it sounds natural. Day 3: Go to a social place where people mingle: a class, a café, an event. Day 4: Say hello to one woman, keep it under three minutes and leave on a high note. Day 5: Reflect: what went well? How did she respond? What would you change? Day 6: Repeat with a new person. Practise asking for a number, and practise accepting a no. Day 7: Rest and notice that you survived. You are already braver than last week.
FAQ
How do you approach a woman without being creepy? Choose a moment when she is relaxed and not trapped, say something simple and honest, keep it brief, watch how she responds and make it easy for her to end the conversation. Creepiness comes from pressure, not from saying hello.
What is a good first line when approaching a woman? Something honest and situational, such as “Hi, I’m Alex. I saw you and wanted to say hello” or a comment about something you are both experiencing. Delivery and respect matter far more than the exact words.
Where should you not approach women? Avoid situations where she cannot easily leave or is clearly busy: when she is wearing headphones, working, mid-workout, alone on a dark street or on public transport late at night.
What should I do if she is not interested? Smile, say something like “No problem, have a great evening”, and leave. Do not argue, ask why or try again later. A graceful exit is the best impression you can leave.
— Maximo Garcia
More from me at maximogarciaworld.com.
