This evening I showed Greg one of my favorite movies:
Electric Dreams. It came out in 1984, and my brother and I watched it multiple times.
It's romantic comedy about a love triangle between a cute, nerdy architect (Lenny Von Dohlen), a cellist (Virginia Madsen), and the architect's computer. As you can imagine, the treatment of computers in the film is both dated and ridiculously far-fetched, but that just adds to its charm.
Electric Dreams also has a great soundtrack, which features Giorgio Moroder, Phil Oakey, Culture Club, Helen Terry, Jeff Lynne, and Heaven 17. Definitely check out both the soundtrack and the movie.