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take a picture
causually after school go up 2 him and be like '________ i want a picture wiht you' if hes like sure then he isnt unconfortable out it but if hes like umm ok and seems fidgity then hes unconfortable. hold hte camera youself and put your hand on his shoulder.. be flirty dont worry obut wht you say, you can get mad at yourself for it later when you're alone :)