The Secret To A Lush Date Conversation Has Nothing To Do With Words


The key to a scintillating and kinetic conversation on a date is one’s ability to ask really good questions. But before we talk about how to ask really good questions, it’s crucial to know what really bad questions look like.

A really bad question can crawl out of our mouths in a number of ways but often falls somewhere on the spectrum of either a boring platitude or an invasive probe.

When one of these slips out, it can alienate or perturb your date, or, in a worst-case scenario, bomb the conversation with the deadliest date killer on planet earth: awkward silence. *gasp*

Fun fact: An awkward silence is technically four seconds, according to science.

Break It Down: What Bad Questions Look Like

There are three signs of a bad question:

It’s too random. While creative questions can be a little “out there” but still fun, a random question has no explainable relevance to the moment. It’s not attached to anything. It dangles like a dongle and puzzles your date. You know you’ve asked a random question when your date responds, or wonders internally, “Why did you ask that?” Yikes.

Example: When your date is describing how she met her best friend, don’t ask, “Would you rather be alone on a deserted island where you can eat only beef or only chicken?”

It’s off-putting. A question that elicits gross mental images, slanders people, or embarrasses your date is a Chinese finger trap of conversational homicide. Keep things profesh.

Example: Your date is talking about a memory he has of a spring break trip with his buddies years ago, and you ask, “But when was the last time you vomited from drinking too much alcohol?”

It’s filler. If you ask a predictable, non-creative question about something you don’t really care about, people make a mental note in their minds that you are a simple-minded person with little imagination. A vanilla question can feel like a cover-up as if you can’t think of anything good to talk about so you ask your date where she bought her shirt. Nice one.

Example: On a hike, a tangible silence besets. Then you say, “So, uh… nice weather, right?” Dude.

The Secret to Asking Really Good Questions

The secret to a really good question isn’t what you’d expect. A brilliant question has much less to do with the words you speak and much more to do with what you’re not saying. To ask a great question that makes your date feel cherished and respected, you must have genuine curiosity.

Genuine curiosity means you put yourself in their shoes. You feel how they feel. You see in your mind’s eye what they see in real life and your imagination generates the thoughts and feelings they have. When you’re in their world, you can look around. You can see what they’re going through and what it’s like to live in their reality. Not only do you look around, but you also find it interesting. When something is interesting, we ask questions to learn more. This is what it means to be genuinely curious.

But there are levels underneath genuine curiosity that require work. You can’t be genuinely curious without first putting in the time to augment your self-awareness and cultivate your interpersonal skills. To get you there, below are seven steps to develop a winsome genuine curiosity.

Seven Steps to Develop Genuine Curiosity

Follow these steps to learn how to ask really good questions and electrify your conversations on a date.

First, you care. If you don’t really care what their answer is, don’t ask the question in the first place. If you ask a question and don’t care about their answer, he’ll see this and resent you for being fake.

Example: In an Uber, you ask your date what they thought of the music at the concert you just attended, but then open your phone and post on Instagram.

Second, you listen. Don’t pick up your phone. Don’t avoid eye contact. Don’t interrupt. Be interested, nod your head, and smile with your eyes.

Example: In the same Uber, you keep your phone in your pocket and put your arm around your date or your hand on their leg, and look him or her in the eyes as they effervesce about the last song.

Third, you empathize. You feel how they feel. You can see in your mind’s eye (i.e., your imagination) what they saw. You can evoke in yourself the emotions they’re expressing and this empathy empowers you to ask a follow-up, bulls-eye question. See the next point.

Example: When your date tells you about an intense job interview, you ask questions that unlock exactly which emotions they were storing up, such as, “Did you feel like you were connecting with one person more than the others?” “At what moment in the interview did you feel most confident?” Do you feel like any of your answers weren’t as good as the others?”

Fourth, you articulate. If you have the first three (you care, you listen, and you empathize), you’re going to be able to ask follow up questions and go into more detail. This is sometimes called active listening. Active listening is powerful because it uncovers specifics in the story. The more specific your conversation becomes, the more memorable and bonding it is. A good follow-up question is natural and well-timed; it stokes the passion and excitement of the conversation to another, more pleasurable level.

Example: In the same job interview conversation, your guiding questions help unpack the story and you make your date feel better about it. “You mentioned they liked your answer about teamwork. That’s great. Where did you learn that?”

Fifth, you reflect. By using non-verbal cues and repeating the words your date uses, you can communicate back to your date that you are listening and understanding their answer, without distracting or hijacking the conversation.

Example: Avoid the resting bitch face. You ask about your date’s family. You make a conscious effort to show your teeth. While showing your teeth is usually what happens when you smile, if you smile too big, your date will wonder if you’re actually listening to his story about his parent’s serious divorce. Keep it down to earth. Showing your teeth is neutral and more receptive than a stone face.

Sixth, you follow. You stick with their story, track the names and relationships, note the details and the conflicts. You’re engaged the whole time. When your date knows you’re keeping up, they subconsciously note that you’re intellectually “with it.” Not only can you keep up, but you can build on top of the question.

Example: Your date is telling you a story about the first time she went to a hibachi grill with her friends and the chef launched a shrimp into her friend’s shirt. You ask, “Ha! What did April do?” Your date smiles to herself, enjoying the fact that you remembered her friend’s name.

Seventh, you read. Before asking a question, it’s important to know if your date wants to be asked a question in the first place. Otherwise, the question may sour the mood. The more self-aware you are, the more you can tell when someone is uncomfortable or on-edge. This will give you the ability to know when to dig deeper and when to back away.

Example: Back to the divorced parents example: You might pick up on the fact that it’s a sore spot with a lot to unpack. The restaurant is too loud and crowded, so you resist asking a follow-up question until the two of you can be in a more intimate setting.