After watching the first two episodes of Princess Jellyfish, I have to say, my hunch was correct. This is a refreshing bit of anime!
Sure, the narrative of opening up the introvert, or transforming the goose into a swan, is very familiar. But turning the expected female mentor, the one responsible for transforming little Tsukimi, into a cross dresser is just pure fun.
The initial episodes, as you can imagine, revolve heavily around making fun of Tsukimi’s social ineptness, as well as that of her otaku crew. There’s plenty of cliché here, but the comedy still works; you’ll definitely laugh. But it’s the developing relationship between Tsukimi and this interesting boy that constitutes the narrative hook. You just don’t know if he will change her in the predictable way, or perhaps something between them will emerge.
Conclusion: you’ll want to come back for more.