A Dark Grey Idea: The Breakup (se5revolution.s3.amazonaws.com)
You move the Day 16/$2000/Charm 200 to the beginning.

As Ryuuji, you start out with money, but you are told your current girlfriend Tomoko is at a bar you dont normally go to.
When you confront her there, she says for 2000, she'll go back to a hotel with you. If you pay her (which is most or all of your money) you get a night of great sex followed by a breakup. If you dont pay, she breaks up with you then.
The bartender then offers to show you "something you ought to know" for 500. If you agree, Toreda shows you a clip of Tomoko doing the charm girl position in the rest room with Primero.
Either way, your girl is a ho.
And as you deal with that information while drowning your sorrows, a guy in a tieĀ  says, "How would you like to get revenge AND make some money in the process?"