what level are you at with his like and hearts? also I'm 90% sure he can only receive the gift at night and the only gift you can give him is wine atm.
off that though there are quite a few ways to get more like than just asking to help him and gift giving, they just all depend on your current standing with him. like before 1 heart you can begin by starting the werewolves storyline and looking for his missing friend.