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how do I get Rei to go race with Roy again at midnight? She keeps on sleeping at midnight with even 90 energy and I can't find the options to ask her to go race with Roy again at midnight when she is awake...

just go with the bike at midnight and she will follow you to the race

it's not working. It keeps telling me to come back with Rei whenever I tap Roy, and Rei didn't follow me to the race as well...

even if you take the bike on garage?

unfortunately, yes. I have already tried many times, and it still didn't work...