Seems to me that the game being set up to accommodate that play style and still preserve the plot is beyond what one should expect. Sounds like going to a rib shack, ordering just a salad, then being put-off that there are no maple syrup or coconut milk based dressings available.
Maybe like with taking over empires, one of Nancy's skills is knowing when everyone else is having encounters. I've never tried to play past Maat without one; I may go see how that works out. Or maybe 'date' is just spending time individually with all the different women, which MC has to do. "Hopeless romantic" is accurate no matter what other explanations apply, as MC's in-game reasons for choosing Annie only are limited to what we see in the text, not to your particular reasons for following that path, which couldn't possibly be reflected in the text.