hi Lily! I am utterly down for amazingly awkward! 😄 For bonus awkward points... was their casual school involvement a public thing, or do we have the extra fun of Draco not actually knowing that his PA once had intimate knowledge of his girlfriend?
Theo definitely knows Lisa heaps and well. I'm sure he got on fairly well with the Ravenclaws (once he got himself together and stopped being quite such a git) and their respective positions have allowed them to renew the association. I'm imagining a lot of sharp looks in meetings and understanding notes in the margins of things and possibly messages at midnight saying "you're still working aren't you?"
Oberon, meanwhile, is amazing. Theo is horrified. He's so flashy and Theo is very definitely not interested in the flirting (spoilers: he lowkey is).
Theo definitely keeps notes on everyone who's royalty and high nobility and important to the running of the court, so if there are things he should hear about regarding any of your list, or you'd like him to cause some trouble or pass some info, let me know!