This isn't my normal type of game but I had a really enjoyable time playing it, great entry :) Your writing is great, each of the characters had distinct personalities and the dialogue felt natural. Often times game dialogue is written in a way that comes across forced and takes me out of it, but I didn't get that sense at all playing your game and all the character interactions and conversations felt authentic. I loved how you had extra NPCs like the DJ, drunk guy, and gambling man. Those extra details made the whole scene feel alive. I never would have thought about making a game like this in RPG Maker and its really cool what you were able to accomplish.
The minigames for each date were another great design choice and each minigame fit the personality of the girls very well. The minigames combined with the little puzzles to solve made the whole thing feel like an actual video game instead of just a visual novel which I appreciated. I was blown away at the custom song after making Elise her pina colada and going to her concert, incredible level of detail for a 10 day jam and it was honestly kind of a banger too. The d20 roll was a cool mechanic and fit Lisa's character perfectly, I re-rolled like 7 or 8 times until I passed the check but fate works in mysterious ways lol.
I do have to say that I find the AI generated art disappointing. I know the character portraits are a big part of a dating sim (and are well beyond my abilities to create so I understand to an extent) but I would much rather see an amateur attempt at drawing them or assets that don't fit the game super well instead. But I do appreciate you being super honest and forthright about it.
That being said, I was pleasantly surprised at how much I enjoyed this game. The writing is excellent and each of the characters have fleshed out personalities that feel real. Each ending I got to was heart-warming and worth the time spent getting there. Awesome entry, and keep up the good work!!