Dating simulators are inherently unsatisfying, in part due to the nature of choose-your-own-adventures. It's hard for the author to tell any kind of cohesive narrative as choices are often so disparate that the endings all require the reader to rewrite the protagonist in their heads to fit that particular branch. And even if one accepts that the player character is a cipher for your personal choices, this only works for one playthrough (assuming you like any of the choices). After that, one is tempted to just read the other branches for completionist sake, which devolves into tedium.
Add all of the above problems onto a dating simulator is even more problematic, as in real life, successful dates are so much more complex than decisions; my wife was drawn to me because of my looks, my sense of humor, and that I accidentally had sunscreen showing on my face when we first met. While I had some agency in all of that, I honestly wasn't trying that hard. I just was who I was. So dating simulators have a difficult time with immersion even for a second. It all just feels like playing with dolls without the ability to use my imagination.
Chris Cornell definitely gets this. Save The Date explores these themes over what makes a story immersive and satisfying. The player is tempted to play this like any dating simulator and constantly struggles against the author who pushes back.
I want to like this more than I did. Given how thoughtful Cornell is about the theme and style of the game, I wish the writing was more lush. There's a lot of stilted dialogue and a lot of clicking past short sentences, which is one of the primary problems with actual dating simulators. But mostly I was annoyed by the ending, as I found it ultimately negating my experience playing the game rather than enriching it.
Others have felt differently, so play it if you enjoy metafiction.