The Highschool Crush

The last contestant arrives in the now-expected flash of light. She's dressed professionally and had mid-length brown hair. For the first time, neither Henry nor Jane seem to recognize her at all. She takes in the room. "What's going on?"

Cassiel says "Ill explain once you've introduced yourself."

"I guess I can do that." She clears her throat and begins. "Um, I'm Liana Watts, I'm 30, I have d-cup breasts, and I'm a lesbian. I work as a librarian, and my main hobby is tabletop RPGs. I'm not sure who either of them is," She gestures to where Henry and Jane are standing "but the woman looks familiar. I'm pretty sure I know her from somewhere"

Jane seems shocked "Liana? No way. You look so different! I'm Jane, remember? We went to high school together!"

Liana's eyes light up with recognition. "Oh yeah! That's where I know you from! I understand why you didn't recognize me, though, I've moved away from the 'cheer captain' look I used to have pretty substantially, haven't I?"

"Sure have! You know, I used to have such a big crush on you way back when. If I'd known you liked girls I would totally have asked you out!"

Liana's face darkens a bit. "It's... probably better that you didn't. I had some pretty bad internalized homophobia back then, so it wouldn't have gone well for anyone."

The exchange trails off, both women looking a bit thoughtful. Cassiel breaks the brief moment of silence. "Alright then, now that everyone is here, I can start explaining what's going on!"

Liana (thanks to @Hardric on the Harem Hotel Discord):