John's cross-dressing stint is milked for all of its humor. Shinon hits on him thinking he's a girl and Haar walks in on an Almost Kiss with John and Jill while John is still crossdressing and pretending to be Jill's sister. And that's among other things.
And the entire cross-dressing stint gets even more Hilarious in Hindsight when it's revealed that there is an ACTUAL Sophia Domivere who is not John in drag.
Fridge Horror: The person who was responsible for the death of Gatrie as well as the cause of great amounts of torment for John early in the story just happened to be a time-travelling ex girlfriend who was also once a friend of Gatrie's and mourned his loss. She also happens to be the same person who killed John in the story. Ax-Crazy much?