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Tell me please If I used the preposition on correctly in the following sentence.

What days do you like to go out on? Personally, I like to go out on Wednesday.

What if I asked the following question,

When do you like to go out.

Would it be the same question.

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Your use of the preposition on is fine there, as for your second question the answer is no. "When do you like to go out?" Isn't as specific as "Which days of the week do like to go out on?" One question asks for specific days of the week, the other one isn't specific at all.

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When do you like to go out?

The question could be asking about time, weekday, night/daytime/dawn/dusk, before/after an activity, etc.

Also, the first question asks "What days do ...?" I think the answer would be "Wednesdays"

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