Anne love path; then you can let her have fun with others (or not, it's your choice).
Very little happen on the love path. It's the one with the least content, and since she doesn't even like to be touched in the library on that path, I doubt she'd be up for any kind of sharing on it ^_^.
You've got to go the corruption path, and agree with Joe and Chris for sharing. Then, Ann will ask if Chris can come to the movies, and you can get her to seat on him.
The choices are basically deal with joe during the truth/dare, let chris give his number to Ann and let her reply to him, dare ann to spend 5 minutes with Joe, agree with Chris during the party. And I think that's about it.
All those are on the walkthrough, as the old choices did not actually change, more scenes were added/reworked, but the old WT is still accurate on the important choices early on.