Can I book two Hilton rooms in one night at the friends and family rate?

Yes, Hilton employees can book hotel rooms for friends and family at half the best flexible rate BFR! A maximum of two rooms can be booked at one time, and thirty room nights can be booked per month per year. What's even better is that you can still get points for room nights by staying at the family and friend rate, and presumably gold and diamond benefits are also available.

The definition of "relatives and friends" is very broad. Hilton employees will have a web portal where they can book a room for anyone. So how do you meet friends who work at Hilton? You might as well ask them for help before your next trip; if not, you can hook up with girls and guys in the executive lounge in the future...