I would love to see that. The amount of whining Chris would do while being forced to interact with "A JERK MALE" would be epic.
All wanting Chris to have a bad time aside, this would be an excellent idea.
I think Chris is a lost cause, that being said, making a huge part of his life something he has avoided , could be one of the few things that does him any good.
If my finger was on the button, I'd pick someone with experience with addictions, hard core criminals, etc. Folks that take every opportunity to fuck up their life.
Helpers (tard wranglers, not trying to be Mr politically correct, just using specific terms as I may have to differentiate.) Come in many flavors, from kids show host esque, to R Lee Emery like.
And imho , someone willing to show up at the drop of a hat to say "Either you stop doing this, or the cops get called." When he is doing destructive shit would do him wonders.
Extra points if it's an LGBT positive individual, as Chris needs that metaphorical slap in the face as well.