A true, “only in New York City” story: A friend of ours woke up yesterday in a fog due to Daylight’s Savings Time, thinking he was late for a brunch date on the UES. He dashed out the door and went to meet his date, but forgot about…the New York Marathon. It turns out that all the traffic that delayed him actually made him on time for brunch. Only in New York…

However, those actions left him out of breath, sweaty and brain-dead. He reported a ton of awkward silences on his date and wondered what he could do to prevent that in the future. We’d suggest remembering to turn the clock back and marking the first Sunday in November as the marathon, but we’ll use the wise words of Scar from Disney’s The Lion King: “Be Prepared.”

Think about it: You would never give a keynote address without some notes to reference, so why would you ever go on an early-stage date without any pre-planned material? Long periods of silence on a first or second date will ruin any chance for future meetings.

It’s not strange to have a few thought-provoking questions in your repertoire, and use them when you feel the conversation on your date is starting to turn cold. These should be questions that require more than just a simple yes/no answer. For example, “If you could be anywhere in the world right now, where would you be?” or “What would be your dream job?” or “If you could have dinner with any person (other than me of course), dead or alive, who would it be?”

For something a little more humorous, check out Would You Rather : Over 200 Absolutely Absurd Dilemmas to Ponder by David Gomberg and Justin Heimberg. This is the greatest icebreakers book we’ve ever come across (occasionally, we’ll break them out during meetings to take a break). The questions are hilarious, like “Would you rather fight Mike Tyson or talk like him?” (make sure your date doesn’t have a piece of ear missing before you ask that one), “Would you rather be followed by a trail of paprika wherever you go or have eyebrows that randomly float around your face?,” and, our personal favorite: “Who would you rather have sex with? Ronald McDonald or the Hamburgler?” (Most people say the Hamburgler, probably because so many of us have a fear of clowns).

If after all this advice you’re still at a loss for words, just ask about your date’s favorite movie, or book, or restaurant. But be sure to add the word “why” at the end of your question! That’s the most important word when you’re straining for conversation. “Why” begets the word “because,” and those answers beget other strings of discussion that will last for an entire day or night.

One exception to remember in early-stage dates is to steer clear of two very dangerous topics: politics and religion. Save those for more serious times in your future relationship.

How do you avoid awkwardness on dates? And how do you get around the New York City Marathon in your neighborhood? Post your strategies below.