Dates don’t have to be confined to the prototypical “dinner and a movie.” Although, for the record, a dinner and a movie is indeed one of our favorite dates.

When Peter (also known as the Man of My Dreams) and I were getting to know each other, we searched for effective ways to grow a flourishing relationship long-distance. My hailing from northeast of Dallas and him residing in San Antonio made us appreciate technology (hooray for video chat and cell phones!) and cherish the moments that we were in the same town.

One evening, Peter picked me up in his trusty Ford Taurus. We drove to the store and snagged the game Monopoly (proof that I lived in a small town: one of the only places open at the time was the local McDonald’s). So we perched at a small round table and pulled out Monopoly, while Peter explained his idea:

Everyone knows that a well-played game of Monopoly(TM) will take days. It’s the stuff of long Thanksgiving weekends and family feuds and never-ending sagas. So why not embrace the reality of the infinite game and make it last even longer?

We sifted through the Chance and Community Chest cards, pondering what each one made us think of. Then, we came up with a question prompt or category loosely inspired by that particular card. If the card decreed, “Pay hospital $100,” the question prompt asked, “What is something you paid $100 for?” If you got the appreciated “You inherit $100” card, you could also answer, “What is a legacy you’ve been given?”

When you drew a card or purchased a property, you answered the question on the card. When someone landed on one of your properties, they answered a question along with paying rent.

Even the process of customizing the game helped me get to know Peter better. Future rounds of Monopoly kept the process going! What to me had been a laborious game of around and around and around again attrition became a gathering spot for conversation and sharing.

This past Thanksgiving, our kids discovered the additions on our set of Monopoly. We tried out a few of the questions on a new generation as we introduced them to the game. We don’t always play the question version of Monopoly. But the prompts are there, ready for a conversation and priming the pump for an ask.

These are the good old days, y’all.

What consistent activity do you do? Do you have family game night, or volunteer with your church high school group, or chat after a workout at the gym? How might you stack a question onto that activity?

It could be as simple as having questions ready for your next board game. Every round, one player gets to ask a question after their turn.

Our already established routines are great places to ask a question, inviting someone you love into a conversation. The goal is natural, non-awkward, and fun.

Need help knowing what questions to ask? Access free conversation starters from my book The Question Habit. They are organized around life stages and range from fun to thought-provoking to deep and real.

Free Conversation Questions