richie - it's got to be the arcade. he asks you to meet him there so he can show off his gaming skills.
bill - you go ice skating. it's the middle of winter, and the local lake is firmly frozen over. couples are twirling around gracefully, while you and bill are plowing everyone down, as the both of you are blushing messes and can't concentrate.
eddie - milkshakes. you don't share a milkshake of course, but he does let you eat the cherry on top of his.
stan - study dates in the library. you help him study with flash cards, but the only thing he remembers is your laughter.
mike - he invites you to the farm, and he attempts to reach you how to shear sheep. it doesn't end well for the sheeps wool, but it does end well for the two of you.
ben - you and him go to his house, and watch movies the whole afternoon. of course, their pg, but it doesn't stop him from screaming at the mini jump scares.
beverly - the quarry. you're hesitant, but beverly has done it dozens of times beforehand, and coaxes you into jumping with her. it was worth it.