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Yes, always always yes. You will regret not doing it 😉
It doesn’t make any sense to tell him that you have feelings when you don’t want to date him. If that’s how you truly feel about dating him then it’s better to end things with him without telling him that you have feelings for him. If you’d like to date him you should tell him that you have feelings for him and ask him out on a date. If he says yes you’ll know that he has feelings for you. There’s no point in holding back because you’re worried about what might happen if you tell him that you have feelings for him.