Ryker really isn't fleshed out too much passed his kiss. But yes you can get passed level 7.
You want to start with the ASK branch and let him ask you questions. then you can pick any question after answering his to ask him. At the moment these answers aren't carrying over if you leave his interaction scene then come back, so it all needs to be done in the same scene.
If he asked you questions and then you go into kiss, you should get different dialogue which gives you the ability to do first kiss then ask him out.