Catherine light-spoilers:
It features a young man, Toby, watching his best friend getting married to a hottie called Katherine. He claims in despair that he'll never win big like him, considering he had an affair with a transgender, but didn't realize it. Such person, Erica, comes from behind and grabs him, to tease Toby.
Kinda shows how different we people can be. If I've ever had the chance to date someone as hot and interesting (she has the best convos in-game!!) as Erica, I'd seriously consider that I've won big. Too bad Erica cannot be romanceable, considering she thinks highly of the main character.
There's an alternative signature (the one I used most, instead of this particular sequence) which Toby demands his virginity back, on which Erica replies that "once that hole is punched, there's no refund!". Whose hole was punched, well...that's up for your imagination.
