Neon Genesis Evangelion: Girlfriend of Steel
Picked it up as a collector's edition in Japan (came with NERV stickers n' all sortsa shite) when it first came out for about 5000JPY.
I'd played through and absolutely fucking loved Neon Genesis: EvangelionZ, which was something like Heavy Rain mixed with The Sims, but in an Evangelion sandbox world. You had to play as Shinji the first time and it started with the berzerker event - but from that point on the angels would come in a random order, Asuka would turn up randomly (you could end up fighting some of the really tough angels with just Shinji and Rei - even Shinji could be injured and you'd have to lay in your hospital bed listening to Rei and the angel blast the shit out of each other), and your actions would influence everyone's respective AT FIELD. You know there's a big angel fight coming? It's important to support the other Children. Unfortunately, as with everything Eva, hedgehog's dilemma etc - you might help their AT Field, but yours is likely to suffer unless you can find some other outlet (I always enjoyed standing in Shinji's room, punching the wall all night. I'm not kidding. That was one of the things you could do lol). Coupled with me essentially learning fluent Japanese from the game within about 6 months (I eclipsed university trained Japanese language students of 4+ years study at this point), the game was masterful. If, like everything Japanese, rather odd.
As a side note - the further play throughs were even better. Depending on how you went as Shinji, you could unlock more characters. And then you could unlock other characters by fulfilling different roles. Work a lot of over time as Katsuragi, and you could unlock Fuyutsui, for example. Outsmart Seele in a chapter? Unlock Kaji. Be a rude prick? Unlock that Osaka kid who was a bully/later a pilot. Hell, you could even unlock Pen-Pen the freakin' Penguin.
But back to Girlfriend of Steel - it sucked. It was one of those daft J-dating sims, but it was set in that Evangelion 'alternate reality' world where there were no angels and Shinji/Rei/Asuka were just regular kids. NG:Evangelionz did the same thing but infinitely better because it wasn't so scripted. Girlfriend of Steel was just like a literal girlfriend of steel - cold, unforgiving, a poor conversation partner, and don't you even THINK of anything ECCHI unless you've got a lot of time to warm her up.