Professor Richard Wiseman, PhD, was just on Good Morning America with his new book, Quirkology. In the interview he said the pick-up line that works 100% of the time is, "If you were going to be a pizza topping, what topping would you be?"
What makes a pick-up line work? Any question that gets someone to relax, open up and talk about themselves. This question is not at all intimidating and certain to illicit a fun conversation.
The line I have recommended over the years is, "If you had superpowers, how would you use them?" This question is fun and it tells you something about a person’s values. If they want to gain power for themselves or if they want to do good tells you what they care about, at least at that particular time in their life. No broad judgments should be made because of their answer, however. If they’re focused on their career and getting ahead they may want to use their power to advance their success. You can follow up with a question about how caring they are such as, "Is there a way you would use your powers to help others?" Then see how they answer. When you’re looking for that special person the list of what you’re looking for should include kindness. You definitely want someone who is kind and thoughtful.
Make up a few of these kinds of questions so you’re equipped when you go to Oprah’s Obama fund-raiser Saturday night. I live in Santa Barbara but somehow she didn’t invite me. Boo, hoo. 
I’d spend $2 grand to be at that party. Talk about interesting conversations.
Oh yeah, the most important aspect of being a good conversationalist and getting that phone number is BE A GREAT LISTENER. Most people don’t get the pleasure of really being listened to so you’ll stand out as an amazing person. But pay attention to whether they ask you questions. If they don’t, that’s a sign that they’re self-centered, a quality you want to avoid like the plague. Give them a little slack because you’ve been asking such fun quesitons but just notice to see if they show any interest in you by reversing the questions once in a while. Or, if they haven’t asked you any questions, offer your answer to the same fun question and see how well they listen. If they don’t your response should be, "Next!"
With much love,
Kara
The Heart Specialist™
"Celebrate Life – Be Happy!"
