Caitlin's scene requires completing Autumn's storyline.
To win spin the bottle just make the boys target the boys and the girls target the girls until Justin leaves. You need 3 things to be true. Justin hasn't kissed anyone. Claire and Georgia have kissed. Georgia hasn't kissed you.
The first is a bug. It's the first of Naomi's pictures I'll fix it in the next update.
The second is a hidden scene. You have to keep asking the Mistress for an extension on your Mana collection every night. Make sure you have Mana, and when she gets mad with you plead with her.
