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>bedwetting
Pyschic type gym which uses the "shared dream" trope, the challenge is that you have to beat the gym trainers in each room in a certain time limit (probably condensed to a turn limit for simplicity's sake) or you have to restart the room, with the implication that you beating them is waking them up. The entrance itself has you get into a bed themed rollercoaster, and you're sent off into the darkness. Rooms are segmented due to the fact that they're only loosely connected coherently, but of course there's lots of water themed imagery throughout which only gets more obvious as you go on. The bed itself changes its theme based on the room.
When you get to the gym leader's room, he's asleep, but takes the bombastic role of the "dream defender" or something equally climatic, and that you can't leave without beating him in a battle. The team would mix theming and effectiveness with sleep based moves. Starmie (night sky, Analytic to punish switches), Musharna (obvious choice, uses Nightmare even though i'm not a fan of that scenario), Bronzong (Bell = Alarm, has the bulk/typing to get one Hypnosis off), Espeon (any theming here would be a stretch, more just a fun choice), and Gallade (uses a moveset to counter Dark/Ghost types, and dreaming of being a hero). If you wanted to break typing, Komala is also obvious and can counter dark types, with the choice scarf/sleep talk moveset.
When you win, you're launched on the coaster back to the beginning room as the leader's room floods. A door opens as the gym leader hands you the badge and Hypnosis TM before saying he and his Espeon have something to clean up, as the Espeon teasingly drags him back to his room...
If you lose on subsequent attempts he makes a subtle claim that drying out your carriage must be a hassle.