Out on the streets of Milan, Russell and Cindy are foregoing the hotel room and trying out the idea of sleeping outside. See? Thank You For Not Sissying. Russell decides to ask a nearby cop whether sleeping on the bench is all right. What he actually asks, though, is whether waiting for a bus on the bench is all right. After the cop tells them yes, Cindy points out to him that although hanging out on the bench is all right, the cop may not like it when they whip out sleeping bags and fall asleep. She's right, I think; if you're going to bother asking permission, you have to ask for permission for what you're actually about to do. Otherwise, it's not worth much. She interviews that Russell can be "touchy...temper...a little bit...just slightly." Next thing we know, they're in the process of hunkering down for the night, but they're still bickering. Sarcastically, he says, "Hey, dumb-ass, it's out of respect you ask them. Do you want to ask them to come snuggle with us?" I'm sorry, did he just call her "dumb-ass"? Gee, I can sure understand why she's so infatuated with him. He does seem like quite a catch. After all, it's hard to find a guy who will call you a dumb-ass, especially when you're right. She comes back with, "If you want to talk about respect, why don't you try using it?" He then voices over that they need to work on "communication." Oh, yeah. He's on the list.
At 2:00 AM, Millie and Chuck, Chris and Amanda, Josh and Steve, and Dave and Steve all take off on their charter bus. Phil reminds us yet again of the whole charter bus situation. Yeah, Phil, I've got it. The second bus will be taking Russell and Cindy, Kelly and Jon, Jon and Al, and Monica and Sheree. The last bus? Brings up the rear with Debra and Steve, Tian and Jaree, David and Jeff, and Chip and Reichen.
We cut to fabulous snowy scenery as Phil explains that the teams are headed to the Dolomite Mountains, to a town called Cortina D'Ampezzo. (Bravo to the Eagle-Eyed Forum Posters who noticed the adorable sign at Cortina that looks like a symbol for "No Bugles." We suspect it means, "No honking.") At 9:00 AM, the first bus arrives at the clue box in town. Everyone hops off and gets going. First to the box is actually AirSteve, surprisingly, but everyone else is right behind him. The clue tells them to proceed to Cinque Torri, which appears to be a mountain. At the bottom of the mountain, they have to board a chair lift, and when they reach the top, they'll follow a marked path through the snow to a route marker. Josh asks a local for help getting to Cinque Torri, and learns that he needs a bus. All four teams correctly locate the necessary bus, and they get to boarding the chair lift. On the ride up, Chris says he's curious about what it is they're doing. "Whatever we're doing, it's really high," Amanda replies. Everyone admires the scenery. Once they're all off the lift, Chris/Amanda, Josh/Steve, and Millie/Chuck all run across the snowy ground toward the route marker. Millie, dressed all in white, smokes everyone else's ass, running like a hunted ostrich. Once again, though, Steve and Dave are taking their sweet time. Dave talks in an interview about how they don't have much of a chance in a sprint to the finish, so they know that they're at some physical disadvantage as compared to these other teams. They catch up with the rest of the teams at the clue box, though, and it's a Detour.