Oh my, I just happened upon this thread.
I remember Tokimeki
, but my first was Sakura Taisen
, which I still play on my Saturn emulator. I never went so far as to go through all
the routes, but I had a blast playing it. The OP still brings a huge smile to my face. (Well, actually, it makes me want to go out in a huge steampunk mecha to defend alternate-Taisho Tokyo from demons, but whatever. ^_^;)
Contemparaneous with both of those was the grand dame of mainstream eroge: Dokyusei
(同級生) and its sequels, Dokyusei 2
(下級生). The games were by ELF, and set up the eroge template that would eventually be adopted as standard: you'd go round the town, and talk to different heroines depending on the location, and the route you get depends on figuring out which heroine is going to be where at any given time. I'd say that the Circus games were their direct successor...
Man, that takes me back. (1992!)