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Dating Tips for Men: How to Approach a Woman Without Being Creepy

Updated on June 16, 2016

So you see a girl out in public who's cute or interesting and you really want to approach her. Sure, no problem! I and every other woman realize that just because a man approaches us doesn't automatically mean he's a serial killer/pervert/stalker, it just USUALLY does (I really wish I was kidding about this). But have no fear, gents, there ARE ways to approach a woman without being predatory.

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Absolutely feel free to:

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1. DO Pick the Right Time

If a woman has her earbuds in on the train with her eyes closed, is sitting in a coffee shop reading a book, or is engaged in conversation with a friend, DO NOT ENGAGE HER. Not only will it probably annoy or disrupt her, but it shows that you think it's more important that she gives you her time than whatever she was in the middle of doing, which is not only assumptive but rude.

So when is the right time to approach? Simply wait until she's no longer actively engaged. Wait till she takes her earbuds out. Wait till she gets up from her book to go to the bathroom or orders another drink. Wait till she's finished talking with her friend. It's as simple as that. Waiting for the right moment will not only make her feel more comfortable, but it also shows that you're courteous, which is a big plus.

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2. DO ask her about herself

This is a basic rule of conversation. Don't go on and on about yourself too much; it’s boring and makes you seem egotistical to a woman you just met. You should aim to make the conversation a mutual exchange, not a tirade.

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3. DO be honest

Don't lie about yourself: where you're headed to, the car you drive, where you live, how much money you make, etc. It's easy to tell whether or not a man is being genuine, so don't lie. She'll be able to tell right away. Plus, honesty is attractive!

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So what CAN you say?

Feel free to compliment her on her style, hair or make-up, facial features, clothing, etc. Anything positive about her that you genuinely mean (that is non-sexual!) will probably be received well. Everybody appreciates a good compliment; just don't be lewd, and don't compliment her too much at once (it seems disingenuous/desperate).

Take it from Mr. Silver Tongue himself!
Take it from Mr. Silver Tongue himself! | Source

4. DO be brief

Don't try to awkwardly extend the conversation or go on endlessly; it's weird. After you've made your introductions, given her a sincere (and non-sexual) compliment, and maybe ask her basic questions (what she's up to, how her day's been, etc.). Then get to the point of why you approached her - to ask for her number, to ask her on a date, or maybe just to compliment her and nothing else. Keeping it brief is a good strategy because not only does it get you a response faster, but if she is uninterested then at least you didn't spend 20 minutes asking her about her childhood, you know? Keep things light, flirty, and casual!

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Under NO circumstances do any of the following:

THIS.
THIS. | Source

1. DON'T stare

You may think it's complimentary, or maybe you just couldn't help yourself, but try not to. Don't get me wrong, I'm not suggesting you should never look her in the eye (that'd be weird as hell), just don't STARE INTO HER SOUL or undress her in your mind. This behaviour screams serial killer. All women can detect it and all women will run for the hills if you approach them after behaving this way.

DON'T. DO. THIS. SHIT.
DON'T. DO. THIS. SHIT. | Source

2. DON'T invade her personal space

This is beyond creepy and predatory. I’m guessing you wouldn’t care for a stranger (even if they were attractive) to completely invade your personal space, corner you, or otherwise block you from walking away, so never do that to a woman you approach (or anyone). A woman in this situation literally begins to fear for her life, so give her a good amount of space!

Being shy is cute, but don't approach if you're not going to follow through!
Being shy is cute, but don't approach if you're not going to follow through! | Source

3. DON'T lie about why you approached her

You're wasting everybody’s time by doing this, including your own. Don't tell her you approached her to say you like her hair if you really approached her to ask her out. Just be honest! It works!

Being sleazy automatically makes you this guy
Being sleazy automatically makes you this guy | Source

4. DON'T be sleazy

Under no circumstances, ever, should you approach a woman you don't know and tell her she's "sexy," comment on her boobs, ass, weight, hips, anything that could be construed as sexual. For the love of god, do not say anything sexual in your first interaction with a woman. Even if you intend it as a compliment, it will only jar her and make her immediately uncomfortable.

I swear to god this is what some men look like when they get turned down and just explode
I swear to god this is what some men look like when they get turned down and just explode | Source

5. DON'T get angry if you get turned down

This is a big one, because I have heard so many horror stories of men who approached women I know, were politely turned down, and then proceeded to get aggressive, use misogynist slurs, harass them verbally or physically, etc. This is a terrifying experience for women and there is NO excuse for men to behave this way. Rejection is a part of life, so just accept it and move along. There are plenty of other fish in the sea, some of whom will be into you.

This is the attitude you gotta have going in
This is the attitude you gotta have going in | Source

6. DON'T expect your advance to be well-received

This is similar to #5, although #5 describes the reaction and this cautions against the mentality that leads to the reaction. Basically, don't be an entitled prick. Just don't. Women don't owe you anything, not even a smile. Most women are too polite to be brusque even if they are uninterested, but some women might be, and that is a chance you take when you approach somebody you don’t know. You never know what her day's been like, so don't take it personally. Again, getting rejected sucks, but it’s not the end of the world.

!!!!
!!!! | Source

A final tip: WOMEN DON'T OWE YOU ANYTHING!

This cannot be repeated enough. We don't owe it to you to be nice or receptive to your advances. We don't even owe it to you to talk to you. If you think women automatically owe it to you to speak to you, smile, go out with you, or anything else, please refrain from interacting with any of us until you've worked through your entitlement issues.

I hope this article is a helpful guide for fostering respectful, light-hearted interactions with women!

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