A lot of guys think that creepy is something you just are or aren't, or that they can't help but come across as creepy if they hit on a woman. I'm here to say that's not true. It's all about approach - and you too can hit on women without coming across as a creep.
1.) Appearance
You can't do anything about the face you were born with, but it doesn't matter as much as you think. First off, make sure you are dressed neatly. Brush your hair. Put away that old stretched-out t-shirt. You don't have to look fancy, but you do have to look neat and clean. Regular showers and the use of deodorant are also important (it's kind of sad I have to say that). You don't have to be Brad Pitt, you just have to not look like a hobo.
2.) Location
One thing you have to remember is that women are taught to be wary of strange men. You don't want to make her feel threatened. This means confine your approach to places where she isn't trapped with just you. A parking garage or deserted street at night is right out. Elevators are generally not a good idea either. Generally, you want to confine your approaches to women who are in public with other people around. Also try to avoid cornering her - for example, if you're on a bus, sit in the seat in front of her instead of sitting next to her.
3.) Social cues on approach
Basically here you want to approach someone who's willing to be approached. A woman who's walking along with her head down and headphones in probably doesn't want to be bothered. Same thing if she's shuffling through papers. On the other hand, if she's in the checkout line idly browsing, or looking around her, she's more likely to be ok with being approached.
4.) The approach itself
Chat her up! Don't start with telling her how sexy she is or opening up with asking for her number. It's unimaginative and makes you seem shallow. Make some small talk, even if it's just about the weather. Ask her what she likes to listen to. Something. After you've talked for a bit (3-5min is enough), then you ask for her number.
5.) Cues in conversation
If you're getting short, clipped answers, or if she's moving her body away from you, she's not into it. On the other hand, if she's engaging in conversation, she's interested in continuing the interaction. And obviously if she tells you straight-out that she doesn't want to talk, even if it involves what seems like a lame excuse, don't push it - she's not interested.
So there you have it - your guide to approaching strange women.
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