Part of me doesn't like it at all--he's a 30-something-year-old man who should be left to live his life in peace, and anything that disrupts that peace should be entirely his own doing. Without mentioning Bluespike (that speaks for itself), the things Jackie wanted him to do in videos (especially public ones) were downright humiliating, and the 'date' he had set up which had him drive all the way to Ohio was cruel. He's not a good person, but that doesn't mean that you need to go that far just to say "haha, Chris is dumb, look what he did for me". We know he's not the smartest, but those were just a few of the things taking it too far.
On the other hand, the more normal personas, the ones trying not to date him or be cruel to him, just treating him normally like any other normal person would, are nice. He has no real friends as far as I know, and I imagine all the socializing he has comes from his mom and Facebook. Giving him someone to talk to who isn't downright malicious or looking for anything in return is kind of nice. He doesn't really deserve it, but it's a nice gesture--even if it's for the wrong reasons. However, I don't think it'll do any good for Chris--even if he never learns that they're trolls, he'll still never take the lessons they try to teach him to heart. I don't really remember it ever working in the past (though if it did, please correct me. I really want to be wrong and know he's learned something.)