Find the right setting:
-Approach her in social settings, where socializing is expected or normal. Do not approach her when she is in public transportation and looking rushed (because this is a space of high creeper interaction and she won't be able to differentiate you from other creepers) . If she rejects you, ya'll still have the rest of the commute to stew in your awkwardness.
-If she is walking fast on the street, she is trying to get somewhere, let her do so.
-Do not approach her if she is walking by herself at night in a hurried manner and is not in a social setting. She isn't feeling safe at the moment.
Then look at her for cues:
-If she has the "don't bother me" expression or she isn't making eye contact with you, leave her alone.
-If she is in the library or coffee shop and her laptop seems to have an intense project up there, let her focus.
-If she has a wedding ring, leave her alone.
-If she seems relaxed, go for it. If you share a joke with the folks around her and everyone laughs, you can see if she laughs along and assess her interest to socialize a little better.
Don't use creeper language:
-and also, find something to initiate with besides comments about her looks. If she is reading a book or newspaper, discuss something related to that.
-non vulgar jokes/humor put people at ease, use them.
-be respectful. Don't stare at her body either. Ask open ended questions, if she doesnt smile or respond back with warmth, she isn't interested, do not proceed to ask her out at this point.
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I didn't assume Chris Brown would have to do anything. I was merely using him as an example.