The fact that I created this imaginary situation in my head, as you say, don't you think it could mean that something is "wrong"? Because those like you who don't see it that way, probably wouldn't see anything wrong either if the choice were presented the way we're saying it could have been presented. I wouldn't get an odd/ilogical vibe from it, neither would you, and we wouldn't be discussing this while all of us would still be conscious of the potential importance of the choice. But I think a CHICK-sided player is lead to feel bad about this choice. If that's the intention, then mission accomplished. If not, then someone made a mistake, and that one was not just me.
As if right now, I know that behaving like a CHICK around Jill has always been the best option... except at the very first time she's directly involved, when the "CHICK" option (stay true to your word) means ditching her -> which leads to her not telling you about Tybalt, which leads to you not being able to tell her you want to fight for her, to help her and to prove him wrong. I don't know if this will be definitive but for sure it will drag her drama and maybe cause some consequences for her till we get another option (IF we ever get it) to tackle the issue. If we're interested in her, by making what feels another CHICK decision we're probably bound to a middle ground between the full disclosure about her problems with Tybalt (and ours) we get if we go with her, and the complete oblivion a DIK MC founds himself in in the path where she never comes to us for this picnic date. Only time will tell what the real consequences are and if this situation can be overturned, but I feel this as a penalty.
Trust me, I know this is a choice to show who I'm more interested in. I know it has nothing to do with affinity, it's just a "do you prefer Jill over Sage, or Sage over Jill?" in case you're still in both girls' path somehow. Because that's the flag that DPC sets in the code. I know that I can't bend reality to appease my wishes (which are NOT getting both girls in the same path, cause I know I won't have both and I understand the choice should be made at some point) but I would have expected the writer of the game to come up with a choice more consistent with the rest of choices presented during the game. That's when everything falls down for me: if I like Jill, I've been "led" during the whole game to make CHICK choices, and now I have to change that mindset to pursue her. Which I understand, I really do: sometimes, when the moment arises, you have to get your priorities right, take the chance and go for it. The thing is that my MC can't possibly know this is (let's say this can be) so important for his relationship with Jill. That's just it, I only want all of you to understand why it feels odd to me.
Tl; Dr: Honestly, I would be happy with at least someone who don't think this is a problem saying "in that situation, going to visit Sage as you promised would be the CHICKest choice"