I'll try to explain the idea...
Tobydawg asks: "Older than 27 years old? Ridden this year?"
I answer yes to both, thinking about Nibali, for example.
Then Armchair cyclist asks: "European? WorldTeam? Surname in second half of alphabet?"
Tobydawg answers inside the frame of 27+ years old and ridden this year, thinking about a specific rider.
Then the next member asks, and Armchair cyclist (or some other member if it takes too long for Armchair cyclist to show up again) answers inside the framework and so on until we guess.
The game basically can go to the point of a single possibility.
When it comes to the concrete names, if someone wants to try luck before the single possible answer, the last answering member (before the one guessing a specific rider) answers and the game continues with next member's questions and answers from a member guessing the name (or some other if it's taking too long for him to show up again... let's say 3 hours is too long, we can make an agreement about that).
That's the idea.
We should be able to work it out along the way or return to the original format.