How far is too far when picking up on a girl?

one time i saw this girl walking with her mom and she seemed to be looking at me so i thought about parking and asking for her number but i also thought that it would be too far so i decided to ask and see what you girls think is too far.
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is there such a thing as too assertive when picking up on a girl?
How far is too far when picking up on a girl?
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