It can be so that your game is bugged. BUT if you started over and still this happens, than you are missing something. Probably something very obvious

So lets get over this from the basics.
First you met with Emily, told her everything that will require to a successful photoshoot sessions. You invited her inside, were polite and respectful and told you love photographing. Had a conversation with cousing about her where she tells you "you she called" at dinner. Then you bought the book, read it, visited Emily and did the shoots. Both. Afterwards you started poking the cousing to make the topic of she wanting shoots pop up, at evening and at the mornings. Right?