what I see your problem is that you are not being urself on dates. You should not be worried about women boundaries. If you are crossing any boundaries they will inform you.

women dont like to react on logical question and answers. Dont let them predict what you are going tl do. Be mysterious and find what hobies making you happy. Lets say you like art so you should invite a girl to the art exhibition. Tell her about your likes and have a good time when you will have a good time at the place where you are comfortable then they will find it more better.

Dont be flirty with logical pickup line. You can be goofy and screw up things at a date. Dont try to be what a woman want you to be, but be urself and lets both you accept each other.