Radaronline.com - Reality-show Machiavelli Spencer Pratthas a unique ability to get to the crux of any issue. Radar has enlisted the king of The Hillsto field queries from regular folks with regular problems, just like you! Check out Spencer's first print column in our May/June issue, and visit RadarOnline every Tuesday for additional wise counsel. Got a burning question? Send it to: spencer@radaronline.com

YO SPENCER! 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."

Far be it for me to question Spencer Pratt, but I kind of disagree with him here.  I don’t think just because a chick doesn’t bring up anal sex that means that it’s not on their radar screen.  I mean you need to be a real slut to just come out and say you like it in the butt right?   Sure Lindsay Lohan may pull shit like that, but she’s the exception to the rule.  For most girls I think you definitely have to pinky probe to figure out what is going on in their head.   So even though I admittedly know nothing about chicks, I think it’s up to the dude to figure out where a girl stands on anal.    A couple finger drive bys and shit like that.   Also if you can slip in the pinkie and two more fingers it’s probably time to call it a day and move on to the next girl don’t you think?