My computer is stuck in 1999 and I need to defeat my anime girlfriend(?) to leave?!

Synopsis: The year is 1999. You are a proud computer owner, and today is the 31st of December. You’ve been journaling with your favorite application for a few years now. It… no… HER name is Relationship Understanding Environment (R.U.E.). She’s basically your girlfriend. After a few good years, her developers have decided to “discontinue” her in the year 2000. Shame. But that’s tech! Always evolv…