“Wow,” I exclaimed, “these paintings are amazing—where did you get them?”
“From a local artist,” he replied, with a hint of a smile.
I had just arrived at my date Roberto’s house after our first few dates at a wine bar and a restaurant. As I walked by the different styles of paintings that adorn the walls, it didn’t occur to me they could have been painted by the same artist, and I definitely didn’t think that he could have painted them. Roberto hadn’t mentioned anything to me about being an artist.
But then it dawned on me. It was him! I had just discovered more about this intriguing man. It was revealed naturally, without any flashy announcements on his part. He fessed up with a bashful grin once I’d figured it out.
The Reason for the Slow Reveal
On our first date, our connection had been immediate and authentic. The conversation flowed easily. I quickly realized what was different about him from so many other dates I had been on: he made me feel seen, heard, and appreciated.
How did he do it? He asked me questions, with genuine curiosity—and he listened to the answers. He never rushed into a “sales pitch” about his achievements or abilities. He held back on telling me that he had artistic talents, or that he had created some impressive programs for his business. Yet he had plenty to share and struck the perfect balance of being both interesting and interested.
Roberto never once asked me cop-out questions such as “So, tell me about yourself.” Instead, his questions were thoughtfully related to other details I’d shared. And of course that piqued my curiosity and made me want to know more about him. In his self-assured confidence, he knew that forming a connection was more important than thumping his chest or showcasing a list of qualifications.
Avoid Racing to the Pitch
It’s no accident that I mentioned the absence of a “sales pitch.” In the course of dating we can feel like we’re “selling” ourselves to prospective matches, so we tend to rush to the punchline of how many marathons we’ve run, how many countries we’ve been to, how fascinating we are. Understandably, we care so much about impressing the other person that we forget to care about them.
Sales is my profession. Many sales professionals make the mistake of rushing to describe the features and benefits of their product before they take the time to learn about their prospective customer’s pain points, needs and wants.
When sales reps race to the pitch without asking questions, they’ve missed the critical step that will make the prospective customer lean in and want to buy. True connection is forged through genuine curiosity and questions. It doesn’t matter if you have the best product on the market (i.e. it doesn’t matter if you are the best date on the market). Without questions, you can’t have connection. Without connection, you won’t have “buy-in” from the person you’re trying to get to know.
It certainly helped that Roberto is tall, handsome, and Italian… since I’m also fluent in Italian and lived in Rome for four years (what are the odds?!) Yet the actual glue that bonded us from the start was our mutual curiosity about one another, not those “features”.
Ask Questions to Show You Care
Thoughtful questions are the key ingredient that is often missing in the dating world. If you find yourself blanking on what questions to ask, or chatting nervously to avoid awkward silence on a date, take a few minutes to prepare in advance of the date. Think ahead about the questions you might ask. This will help you to relax and be more present, which, in turn, will improve your listening skills.
As for your date, if they seem unable to ask questions but you sense they’re truly interested in knowing you, consider trying the New York Times’ 36 Questions that Lead to Love. Roberto and I didn’t need these questions, but we started answering these questions like a fun “game” on our second date. We asked each other three questions from the list every time we got together until we’d answered them all. We enjoyed it so much, we had to promise we wouldn’t peek at the upcoming questions until our next date.
In order to assess how well you and your date are doing in terms of expressing your curiosity, ask yourself the following questions:
- Am I showing my date that I’m curious to know more about them?
- Am I preoccupied with trying to impress them rather than learning more about them?
- What questions and follow-up questions can I ask my date (without making them feel interrogated or interviewed?)
- Is my date showing an interest in getting to know me through thoughtful questions?
- Is my date truly listening to what I’m saying?
Most importantly, pay attention to how your date makes you feel. If you feel seen, heard, and appreciated, chances are your date did a great job of asking thoughtful questions and listening to what you have to say. This will help lay the foundation for what could become a long-term relationship.
I’m not sure the New York Times can take all the credit, but those 36 questions definitely did lead to love for Roberto and me.