It depends on the situation.

I have a weird sense of humor and police psychology training, so when I do speak to someone I've never met before, I'll usually start with a bit of humor, such as a totally unexpected answer to a question if they speak first - then observe the response I get. Once I see the response of the other person, I'll tailor the next question or my own response to the person accordingly.

If I have to speak first, the police training usually makes itself evident - I can either directly or discreetly question someone until I extract enough information out of them to determine who they are and what they're doing there. Most of the time though, people speak to me first, so I tend to respond with humor.

Sometimes, a situationally appropriate Three Stooges line works best, since most of the time I'm around males at work, if some walks into the room and goes "Gentlemen!", I'll deliberately look around the room and respond "Gentlemen? Where!?" or "Gentlemen? Who came in?".

If a mutual friend introduces me to someone at work, like "Max, this is Heather, she'll be working in Scheduling", I may respond "My condolences." and give them a dead pan look just to see the reaction of the person and see if they have a sense of humor.

If the person has a clearly ethnic name I recognize, or if I've already overhead them speaking a language other than English that I can recognize, I may respond in Spanish, Polish, or Mandarin Chinese as an icebreaker. My Polish inflection and pronunciation is "spot on" when it comes to time of day appropriate greetings, and it's a huge ice breaker when dealing with some of the people I come into contact with.

So, most of the time, I'll just drop a humor bomb as a way to break the ice, since it's already intimidating enough meeting someone who stands nearly a foot above you and is immovable as a brick wall. :)
Source(s):
Personal experience and police psychology training. :)

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I like to ask people this question:

"If you had to choose between having 10 minutes on the moon or a year in Europe with a monthly stipend of $2000 (can be substituted for another country if they happen to be European), which would you choose and why?"

It's from the book Sex, Drugs, and Cocoa Puffs by Chuck Klosterman. I think that it can, surprisingly, tell you a lot about a person. I'm a moon girl myself.
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I am thinking about trying this one next time: So, do you like baba ganoush?

If they say yes: Well sure, I think baba ganoush is the perfect food, and it's fun to say. So, would you like to get some baba ganoush with me.

If they say no: I will say, don't worry, baba ganoush is not my name, I just think it's fun to say baba ganoush and it sounds better than anything else I could think of :-)

If they say I don't know what baba ganoush is. I will say it's just a type of food that tastes better than it sounds, want to get some with me?
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Well, my wife doesn't really like it when I use pickup lines... but there is still a place for them in my life.

It's tough to meet people (men or women) at conferences or other social events where you really want to get "out there" to network. So, this still may help.

In short, I try to think of simple, topical things the morning before. I'll pull 3 headlines that I can talk intelligibly about and keep each of them in my head. Mahalo (main page) is especially good for this. Mass appeal topics are best... nerdy science stuff doesn't work very well.... even with nerdy science folks.

When presented with the opportunity to start a conversation from "the cold", I exchange names and pull out the topic. Here's an example:

Me:
"Hey, I'm Rob. How are you?"

Them:
"Oh hey ... I'm Stephanie."

Me:
"Nice to meet you. I just heard that one of the kids from the Harry Potter movies was busted for having a pot farm. Have you heard about this?"

From this point on, it's pretty easy to make small talk and steer the conversation towards whatever you want to talk about.

For me, it's helpful to think about what people will be interested in talking about. For example, at a web conference with a large social networking influence I'll try to find a news tidbit about maybe Twitter or other social network.

The most important thing that I was taught about communicating with people whom you don't already have a relationship with is this: Ask more questions than you answer. People like to talk about themselves and in general, you'll learn more from a person by listening.
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