This is actually an interesting question, well done.
I think at first Han, noticing that boosting confidence, would have loved him but since we all know Han is not just a cocky fellow, I don't think he would have approved of his crying over himself and especially his unstoppable ambition. Han is probably one of the least ambitious characters in the whole series. However, if Anakin had not been parted from his daughter and had watched her fall in love with Han he would have certainly approved of him and they would have liked each other very much.