Digital: A Love Story is an extraordinarily charming game -- a sort of text adventure in which you use your new pre-VGA computer to dial up all sorts of interesting BBSes, just like we did in the Old Days. There, you make virtual friends, uncover a mystery, and have the opportunity to fall in love.
The graphical frame and chiptunes evoke the period and place perfectly; the gameplay is awkward at times, and indeed, can hardly be characterized as gameplay at all. That is, there are no real options, just plot points to unlock, though with some mild puzzles to unlock them; it's more of a "visual novel" than a game, though of course it isn't terribly visual. You can get stuck at times, too, if you fail to take the right action to unlock the next bit of story, which requires a frustrating "do everything" approach to resolve, a typical failing of many graphic adventures, of course.
Still, the writing is remarkable, the characters feel real, and it's note perfect for what it is.
Portal
Sounds great. Also sounds like a successor to Portal (the 1986 one, not the 2007 one). It was also a text not-really-adventure explored through a simulated interface, though they didn't have to fake the pre-VGA look. I'd recommend it as a comparison piece to Digital if it were actually possible to Google down a copy.
Takes me back!
I remember these days well.