The common wisdom about socializing is you just have to ask the first question. On one hand, we agree. The first question is the hardest, but for that first question to work, it’s important to ask a question that leads to a conversation. The topics we’re suggesting are ones you’ve probably discussed frequently, but each opens the door to long conversations that can meander in different directions. After all, the goal isn’t just to break the ice but to meet someone new.

If you live in a city, chances are many people you’ll meet moved there from elsewhere. Yet after a few years of living somewhere, it’s awkward to answer the question “where are you from?” Am I from here or not? You can get a more interesting response from the question “Where did you grow up?” which may eventually lead to the story of how they ended up in their current location. Or if they say “from here” you can get all the details of how the city has changed. (And hopefully learn about that locals-only spot that is still around!)

Books are another great conversation topic, but so many of us struggle to read as much as we’d like with our busy lives. Instead of asking, “what are you reading now?” try “I’m looking for a new book to read – any recommendations?” The two of you can discuss different genres, favorite authors, and books you plan to read before you start lamenting that you rarely get around to actually crossing books off that to-read list.

Commenting on the food at a party is always a good starter, but where to go from there? Stay on the same topic and ask if they cook. If they say yes, you can exchange favorite recipes. If no, chat about restaurants you’ve enjoyed lately. To then get more personal, inquire about their favorite food as a child. Perhaps you can bond over your childhood love of deviled eggs.

If you are at a networking focused event, leading with questions about work is appropriate. Another great question is “what brought you to this event?” Many job seekers assume everyone else at the event is either job searching or head hunting, but their attendance may be because of a personal connection, an interest in the keynote speaker, or a passion for the charity group the event is funding for.

Whether a networking event or more of a social party, if the topic has turned to “what do you do?” learn more about the person by asking, “so, what got you into accounting?” People’s paths are often more fascinating than we’d assume. Maybe they were an accounting/art double major and still paint every day.

Looking for an open-ended, non-work related question that works in any situation? Try “what do like to do for fun?” or “how do you spend your free time?” You’ll often learn the most about a person by learning about their personal passions.

Image originally from our September 2010 issue. Read the full story here.