And in just in case you’re asking yourself “who on Earth would want to do something like this?”, I’ll have you know that this sort of anime-style dating simulators are very big in Japan.The game is a lot better than it first sounds and it is freeware so you only have to spend your time in order to find out if you'll like it or not.Off the top of my head I'd also recommend Majikoi, which is currently only readable through a fan translation but will be released by JAST USA sometime in the future.
For visual novels I really would recommend Katawa Shoujo, the "disability girls" game.
I haven't played too many of the former definition but the Sakura Wars games are a great mix of dating sim and strategy RPG, I'd highly recommend So Long My Love on the PS2 or Wii.
Also, there isn't a full fan translation available for it yet, but I played a demo for Amagami a few years ago and it was pretty good.
Like, it's basically fine, but nothing in there was particularly doing it for me either.
I did the Emi and Haneko routes and gave up halfway into Shizune's route because communicating with her was exhausting.
You have to love Japanese culture, especially in the world of video games.