Is there a character from a dating sim who you really like despite disliking the game she is from? Or I guess a character who you feel deserved a better game?
This is a really great question! I had to think about this one for a while because, if I'm being completely honest, dating sims are just big enough time sinks when you put multiple runs into them that if I'm not enjoying the actual mechanics, the writing really has to step up to the plate for me to stay invested in it since there's always more games I could otherwise be spending my time researching. In my experience, that hasn't often been the case, so if a game isn't grabbing me mechanically, I tend to move on after several hours since usually I don't find any routes that turn out to be diamonds within the rough. Sometimes there are games that I would call just fine, but not particularly remarkable 20-plus years later like the True Love Story series from Enterbrain/Kadokawa (ie: their pre-KimiKiss/Amagami series), but in my experience, dating sims are very much so a series of peaks and valleys throughout pretty much the entirety of their golden years in the 90s and 2000s.
Knowing that, I'm going to offer up a bit of a curveball answer and say: the entirety of Yuuwaku Office Renaika for the PS1 published by Takara. Yuuwaku Office isn't a game I would particular describe as a classic or widely remembered in Japan by any means. In a lot of ways, it's the quintessential Tokimeki Memorial clone released at the height of that gold rush. Its main claim to fame within that time period is, as the name suggests, that the gameplay takes place in an office rather than a school. So instead of different characters representing different school clubs, here, they tend to represent different departments or corporate positions and the day to day proceedings therefore revolve around office life, complete with sales goals, lunch breaks, and the like.
For what it is, Yuuwaku Office is decently competent in execution, if largely a game that's looking at other people's ideas and covering them up with corporate themed pastiches. But it is the kind of dating sim that a lot of foreign people crave overseas, which is to say, one with an adult cast and I have a personal soft spot for a lot of the character designs. The writing isn't anything to write home about, but I think if you brushed up that and streamlined the gameplay a decent amount while keeping those characters intact, you'd have a pretty neat cult classic.
I still think about this game a weird amount and glance at it a lot whenever I pass by the shelving that houses my dating sim collection. One of these days I might just finally power through it anyway since, for as much of a clone as it is gameplay-wise, there actually isn't a whole lot specifically like it throughout the history of the genre... 🤔