Pic vaguely related. When playing persona 3/4/5 it slowly dawned on me how it's kind of fucked up that the game incentivizes you to always tell people what they want to hear and change your personality constantly to match the situation (swapping personas). It further encourages this by granting gameplay benefits for ranking relationships up, and at least in the case of 4, locking the true ending behind being the most efficient at getting people to like you.
I haven't played many visual novels/dating sims, but from my limited experience the interesting ones tend to acknowledge this in some way. Doki Doki gets kind of close with it's meta fuckery but the focus is more on how being a visual novel character would suck than about player manipulation. Echo nods in this direction in some scenes where people notice how off the player character is acting, but it's mainly about gay trauma and some other stuff I think I don't get because a) I'm not from a decaying american small town and b) I'm not a furry. Not in the genre, but I thought that was where Deltarune was going with the weird route, but the recent lore dump points more in the direction of commenting on sequence breaking/glitching the game for some as of now unknown purpose.
I feel like the premise of a game calling you out for acting creepy as fuck is obvious enough that something like this must already exist. Does it ?(reccs for good VNs in general are also appreciated)
I'd give persona a bit of a pass because it really emphasizes the importance of getting out there. Persona 4 in particular because you make the most of the small town you're in. Plus, I owe a little bit to the game because it gave me some inspiration to go outside more. Also, Yu Narukami isn't necessarily supposed to be a perfect reflection of the player. The game may be marketed worldwide but assumes you're Japanese so I had to google a lot of stuff for any of the school answers, cooking minigames, or anywhere it might be relevant. Plus, you cannot select Yu's gender.
As for personas, I would argue that they are fragments of Yu's personality that have remained hidden from him until he was ready to use them. As he connects with others, he learns more about himself as well. Or at least that's my take.
spoiler
Also, this video contrasts the player to Adachi, someone who became a dangerous sociopath thanks to completely isolating himself, leading him to become not so well-adjusted. Another thing about Adachi was his narcissism, he writes off Inaba entirely while Yu makes the most of his time there. This video explains it better than I can
https://www.youtube.com/watch?v=WkcmxrkHXD0
That being said, I'm not writing off your ideas OP. The fact that it is a "game" can definitely be creepy and it's legitimately a good idea to make a game that deconstructs the trope. If you want a game that's a little bit less creepy, I recommend Hades. You start off being familiar with almost the entire cast, and while the keepsakes will help you a lot. Knowledge on who the cast is mostly your reward for talking to them. Technically I "beat" the game which done by succeeding in enough runs, but there's so much dialogue, achievements, and I wish to complete the fates list so there is more than plenty of post-game content as if you never really beat the game.
You can even choose to date Thanatos or Meg, and both of them are completely fine if you wanna date both.