I'm not sure if it's been resolved yet, but chris still acts like a friend in the dreamscape despite being on a break.
i figured it out i think unless its a bug, but in the club, you actually have to go over to chris, and the break seems to work then. If you don't, and delay it until the next day when chris puts you on break himself, it wont work, and the dreamscape remains as friends only. This worked for me anyway.