While building a relationship with your AI is reasonable in some ways, it does raise concerns as it could quite easily make human relationships appear at some point to be simply too much trouble, or toxic.
There was a sci fi story that I read many years ago about clone handlers on another planet. One good handler could run up to nine clones in the field, using a kind of technological telepathy, to direct the clones to mine or process product. In the off hours as many did, the protagonist frequented the company supplied brothel.
There was one sex worker he frequented more than any others until he saw no others. Eventually, he fell in love with this woman, only in the end to realize that "she" was just another clone. This was something the clone handlers found disgusting as they manipulated these every day and felt them a lower form of life, which essentially, they were.
When he found a telepathy tech unit beneath the bed, he finally came to realize that he had fallen in love with himself. He was therefore, more or less having sex with himself by proxy.
My point is that in "dating" an AI type personality, a person would basically be dating themselves. As the AI "earns you it shapes itself to fill in your needs, which would be the ultimate form of what can only be considered technological masturbation; the ultimate form of narcissism. We already have quite enough narcissism in the world, more than we need really, in government, in social environments and in interpersonal relationships.
Part of what makes us human is not that we exactly fulfill one another, but approximate it in as much as we can comfortably handle. It is in part within those differences that we find fulfillment in human relationships. Many times it is the unexpected in the relationship that endears us to someone and not in the exactitude of being complimentary to another personality. As I had posted the other day about music, it is in the "inexactitude" that the true quality and affection of human performed music comes across to us.
Yes, that could all be programmed in, but don't we need technology to bring us closer together and not further apart? We are presently already seeing human relationships, true physically close human relationships, suffering. In some countries, like Japan for instance, there is already gap growing between close intimate contact. True, there are robots now that are giving shut ins fulfillment and that is one thing, and I believe it is a good thing, but it will only speed up what I am talking about.
I just think we need to be careful about this. In my short sci fi story "Simon's Beautiful Thought", his AI does him a great service and if that is how things will go, then good, great, that is how it should work out. Our robots and technologies should aid us and not work against us, or inadvertently through artificial means, increase the distance between human beings. But if they do, where will that leave us,as individuals, or as a race of beings?