What are some good questions to initiate conversation with strangers?

[kenberman]

What's your favorite Duran Duran song?

[surfinillini]

Hey now...wanna get out of here and do some [insert drug name here]

now this is hit or miss, but when it hits your good...

[malokoman]

Do you live alone?
Where do you live?
Do you work late at night?

[Duffman]

So, this bum is sitting on a bus. A few rows ahead of him, there's this professional looking man, and in the row ahead of him, there's this hot brunette. The bum watches as the man leans forward and whispers to the brunette, "Tickle your ass with a feather?"

"What!?" cries the shocked young woman.

"Oh, I said, particularly nasty weather." the man replies.

"Oh," says the brunette. "Yes, it is". At the next stop she gets off and a redhead gets on, who sits in front of the professional man. A few minutes later the man leans forward:

"Tickle your ass with a feather?"

"Pardon me!?"

"I said, particularly nasty weather."

"Oh! Yes." A few stops later, the redhead gets off, and a blonde gets on. She sits in (you guessed it) the seat in front of the professional man. A few minutes later,

"Tickle your ass with a feather?"

The blonde turns around and smiles, "Your place or mine?" The two of them get off at the next stop.

Through all of this, the bum (remember him?) has been watching. It took the guy three tries, he thinks, but he finally got there. I'll have to give that a shot, thinks he.

At the next stop, a bag lady gets on. She sits in front of the bum. The bum leans forward and drunkenly slurs, "SHOVE A FEATHER UP YOUR ASS??"

The bag lady turns around, "What did you say??"

The bum says, "Oh, uh... PRETTY [censored] COLD OUTSIDE, ISN'T IT?"

Thats awesome.