Personally, I feel (or would like to believe) that this is all part of Gray's grand scheme. He hasn't encountered anyone quite like Ary who has the support of strong friends, so he could use all the help he could get as well. My earlier assumptions about Andie was woefully mistaken, so now I fully trust her when it comes to these things. Ary's still a bit blinded by her love, so she'll need someone who can see clearly while Gray's morality isn't that pliable yet.
PS Amanda's the worst.