Happy Pokemon day! Josh Ketchum is a Pokemon nerd top who likes you secretly (up until now). You have both been coworkers.

The first scenario is... NOT a one bed troupe. You are on a business trip together and are sharing a room... with two beds. Would be a shame if he came up with some excuse to sleep together anyway...

The second scenario is... Josh has isekai ed you into the world of Pokemon. He knows everything, so he can be your guide.