Ps2 games with dating sim elements
Very little known release from the end of the fourth console generation. The game has dialogue options and actually puts you on a timer to respond. It's more of a strategy game, but the dating sim part is probably better than anything you can find out there that is translated to English.
It has tons of dialogue and options and what you pick actually effect the game play.
It's also fully voiced from start to finish, including optional conversations.
Just make sure to get the US version instead of EU in case you value dual audio.
That's not a sim, that's a passive viewing experience.
Just because you have to hit "x" to make the next dialogue bubble pop up doesn't mean anything.
While I haven't played Fallout, the whole game is basically a treasure of choices.
Starting with Chapter 2, the game introduces you to an affection system which revolves around the female members of your party.
Sakura Wars: So Long My Love is EXACTLY what you're looking for. It's an anime date sim except everyone is a mech pilot so you have RPG combat every so often.
In that period, you don't get to be Sega flagship game with five sequel without being good.
Riviera: The Promised Land (PSP) is excellent in this regard.
I played a bit of Persona 4, and really liked the set up and the anime cutscenes.
The jobs and social systems seemed like they didn't require enough input and were repetitive though, and there was less and less voice acting as I went on, just text, and the voice acting besides Troy Baker wasn't very good, the teen girl characters sounded like they were voiced by women over 30 years old trying fake high pitched anime girl voices, and the dungeon grinding became too repetitive. I'm at the point where a female character gets taken into the TV world and you have to go through 7 levels of the dungeon to rescue her. I've also tried the beginning of AR Tonelica Melody of Elemia.