Based on the personality traits you've described—rude, talkative, mean, sassy, nosy, confrontational, confident, sarcastic, opinionated, stubborn, and sometimes experiencing sadness—it's likely that he will approach his crush with a combination of playful teasing and bold confidence.
His level of "freaky" might lean toward being cheekily provocative rather than overtly romantic. He could flirt by using humor or sarcasm, which might come off as edgy or challenging, rather than conventional sweetness or charm. This could involve playful banter or even a bit of mockery, especially if he feels secure in his confidence and doesn't mind pushing boundaries.
Given his confrontational nature, he might also engage in debates or discussions that come off as intense, showcasing his opinions on various topics. However, his moments of sadness might surface, providing glimpses of vulnerability that could make him seem more complex and relatable.
Ultimately, while he might initially come off as a little "freaky" in a cheeky and confrontational way, his deeper emotions could add layers to his interactions, making them interesting and multi-dimensional rather than one-dimensional flirtation.