I understand what you are saying. It wouldn't appear grindy if, instead of visiting the same woman every day at the same time, time and time again, there were different locations for her and different activities to advance her affection and/or corruption, with less emphasis on racking up the points, and more emphasis on each point requiring some work for it and being a significant milestone in the relationship. Sometimes the dialogue changes a bit each time the woman is talked to, but that doesn't really reduce the grindiness of the time skipping.
I guess I agree with your sentiment, as I have found the time skipping method more efficient than the multitasking method that Evangelion suggested, but I wonder how you imagine a better way for it to work out. I've already spent some time pondering it, but I'm not sure there's an easy answer, because the game is largely a sandbox. In Treasure of Nadia, the story advances in a linear direction, so it can be easy to advance everything as events play out, but in a sandbox like ASWS, everyone's plot lines usually advance separately, so time has to be dedicated to each one. Any thoughts on how to make a sandbox like this less grindy for relationship development, or at least an enjoyable grind?