Five Key Questions to Ask Your Date


My wife has described our first date as the best she’s ever experienced. I say the same about our second date. To me, the difference was our conversation. We met up at a restaurant in Manhattan Beach for our second date, and afterward, we walked along the shoreline and talked deeply about our lives. There was just one problem. The sun was blazing hot, and I had forgotten to put on sunscreen.

My ancestors hailed from Ireland and the UK, so my skin reacts to the sun much like a fork in a microwave. Even though I knew I would pay for this conversation with a bad sunburn, I thought the pain would be worth it. And it was. Eleven years and two kids later, I’m glad my skin burned a little, so my heart could burn for my eventual wife.

If you’re looking for the person worth “the pain,” I created a game called You’re Pulling My Leg! that has over 600 questions designed to get to know the people you’re playing. I originally created the game for a good friend who was dating a woman he hoped would be his future wife. She was! Here are five key questions to ask your date from my You’re Pulling My Leg! game:

Tell me about a time when you avoided someone.

If someone shies away from conflict, they will likely avoid a person, and this question will help you discover if that is true of your date. Most of us have avoided someone in our lives, so be sure to follow up this question with more to discover if this is a pattern of behavior or something your date is actively working to improve.

Tell me about one of your favorite friends.

Though this question might seem benign, it will create a window into the person you’re dating. Is their favorite friend someone you would like to know too? Someone who brings out the best or worst in your date? Is it someone they’ve known for a long time? Be sure to delve deep with this one as I think you’ll discover the quality of that person’s friends say a lot about the person you’re dating.

Tell me about a time when you felt helpless.

Oh, life. If you live through enough of it, you’ll realize you are genuinely not in control. And, if you’re close enough to the people around you, you’ll encounter times when you’ve done your best but can’t help the person you love the most. This question will help you get to the heart of the person you’re dating, and if they’re willing to be vulnerable with you, you’ll get to see more of their real heart.

Tell me about a time when you stood up for something.

Is your date someone who goes with the flow or stands up for what they believe? This question will help you discover how they approach life and might even give you a glimpse into what they see in their future.

Tell me about something you have recovered from.

We’re all works in progress. This question will give your date the chance to tell you about something in their past that they worked through, or they could describe overcoming a nasty cold… Either way, you’ll get to see how they approach the times when they’re down, and that’s important given how many ups and downs the rollercoaster of life has in store.

Of course, if you don’t get to these questions while you’re playing You’re Pulling My Leg!, there are still 595 others that will help you figure out if this is the right person for you. You just have to ask.

About the Author

Allen Wolf is an award-winning author, filmmaker, and game creator. His company Morning Star Games also publishes Slap WackyJabberJot, and Pet Detectives as well. Allen has won a total of 38 awards for his games, which have been played by hundreds of thousands of people around the world.



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