And with this Q & A - YO SPENCER jumps the shark!!

How long do you have to date someone before it's appropriate to bring up the possibility of anal sex?

If you're dating a guy, right away. If you're dating girl, I think you'll know pretty quick if she's into that. If they're not bringing it up, it's not something on their agenda. That's just realistic. My boxing coach Dirty Phi says, "If you stick your pinkie in there, and then another finger, and then another, and she responds happily, then it's cool."