It sounds like you have brought up quite explicitly and repeatedly what you would like in this area and the T is not compliant. Maybe better not to expect and push it then with her as she is unlikely to be helpful. I don't know if a therapist could be useful with this, it does sound more like what a life coach might do. Or maybe even another T who practices a more pragmatic approach. Although the fact that you seem to struggle with dating probably shows that there are some blocks that prevent it to be smooth and successful, and maybe exploring more deeply what makes it a challenge at all could be useful? In any case, if I found multiple times that someone is not helpful in a particular area, I would stop pushing. No one is good at everything and it sounds like this T is just not a match for you in the dating issue area.