We could consider the emergence of a friendship like this a milestone, a bit like when chess AI got good enough to beat a typical club player, but wasn't quite ready to beat Kasparov. We're probably only a few years away (OK, maybe 10+, but it's not 50+) from the Kasparov point, where an AI like Siri can beat the turing test for any living human.
There are all sorts of questions like whether, to be considered alive and imbued with the inalienable rights that should come with sentience, is self-awareness necessary, or is the anthropomorphic perception of nearby humans more important? Should an AI have similar rights by proxy as a pet dog?
One especially important question is what does it mean for an AI to die? If Siri developed a fault, and fixing that fault would cause a change in personality so that it was no longer recognisable to Gus as his BFF, should that act be called "roboticide"? Such questions are particularly relevant when AI/ML systems (deep recurrent nets, for example) are so complex that we don't really understand them fully, so we have no way to surgically correct specific faults; all we can do is revert to an earlier state and re-train. That may be loss of life, for certain definitions of "life".
As an occasional game developer, I tend to think about these issues in other contexts too, such as our relationship with virtual characters in games. It's already very easy to get highly immersed in single-player virtual worlds, like any of the Elder Scrolls games. Most would not be fooled into thinking that an NPC is "alive", but it's certainly possible to develop emotional reactions to certain characters that we perhaps like because they say nice things about us, or dislike because we find then annoying, etc.
There are two kinds of character interaction a person can have in a game: NPCs and human avatars. As we start to build virtual worlds (partly spurred by the Oculus Rift and partly just because of the Internet), this could affect not only our relationship with NPCs, but with other humans too. I don't know whether this will a net positive or negative thing, but we're certainly going to learn a lot about human psychology as we head towards the point where, in VR, nobody knows you're a human.