Rolling the dice, directly refers to pressing the Urban Dictionary Dice button in order to generate random terms hoping to get a term describing a sexual act in which a couple is to carry out in real life.
Stuart: "Hey dude, what are you up to tonight?
Scott: "Not sure man, probably just rolling the dice."
Stuart: "Nice Courtney and I rolled the dice last night, and we got "Butt Rape"
Scott: "I bet she's sore"
Stuart: "Yeah she's struggling to walk, but man my cock was covered in shit and blood. I still came so it was a good night"