[Gallagher]

there's a level of randomness as well

so

there are 3 prize tiers. best is the companion, worst is the shared pool of rejection items

in the middle, each date has their unique equippables, like jello's collar and albert's book. which of their equippables you get from the list is random, but if you're getting equippables at all, that means you're not on the right track to get the companion and have to alter your path/look for more positive choices.