It's basically a popularity contest. The more people you know and are friendly with, the better your chances of winning. You can do lewd things during to boost your chances further, but that only goes so far
SORRY I DIDNT SEE THIS TRY WEARING THE COLLECTIVE CHEER UNIFORM YOU CAN BUY I THINK ITS FROM ONE OF THE STORES I'll have to check to be sure, but that's how i won, I tried being friends with everyone and being a cheerleader but that didn't work, maybe it all goes together!! I hope that helps
Oh also i may have made sure to wear nothing but the top and skirt😭😭😭😭😭but nevertheless I had to try like 6 times before winning with different things the only thing that surely worked was the collectable cheer outfit i would still advise doing it all together just in case
