Based on that personality, he might lean towards a pick-up line that's both teasing and assertive, something that showcases his confidence and sarcasm while also hinting at his interest. Here are a couple of examples:
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"Do you believe in love at first sight, or should I walk by again and give you a better chance to appreciate my brilliance?"
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"I must be a bad habit because I can't seem to get you out of my mind — but don't worry, I'm worth the trouble."
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"Are you an enigma? Because I can’t figure out whether I want to solve you or just enjoy the mystery."
These lines mix his sassy side with a touch of charm, making them fitting for someone with a bold and confrontational personality.