So.. Many.. Ideas..
Princess Proletariat Plays: The guys have to play princess Barbie girly type computer games. I think it'd be hilarious to be honest.
Prole Dance Battle: Have a bracket, different people go head to head to see who is the true Proletariat Dancing Queen (my money is on Paul)
Online Cards Against Humanity: Hopefully set up so viewers can play along.
Iron Chef Proletariat: People get a set of random ingredients and have to make a three course meal in the office kitchen (I assume you have one?) Jesh, Gordon, and Seth can be the judges.