The Secret to Lush Dating Conversations Has Nothing to Do With Words
Dave Schools is the cofounder of the conversation starter app, Party Qs. He curated the 2,150+ high-quality questions in the app (i.e., Date Night is the most popular category). Party Qs is free and available on iOS and Android.
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.
Breaking It Down: What a Bad Question Looks Like
There are five signs of a bad question:
1. Bad questions are 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?
2. Bad questions are 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?”
3. Bad questions are filler.
If you ask a predictable, non-creative question about something you don’t really care about, people might make a mental note in their minds about you. 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, an impregnable silence besets. Then you say, “So, uh... nice weather, right?” Dude.
4. Bad questions are closed-ended.
Questions that have one word answers aren’t great for really getting to know each other. A yes or no question isn’t a good conversation starter. Usually, an awkward silence follows, especially if the person responds with just one word. “So do you like politics?” … no. …*silence* The same can be true for binary questions where there are only two options (Are you a fan of this restaurant or no?). They don’t prompt more thoughtful answers or stories that really deepen your connection.
Example: Do you like cheese? Yes, I do like cheese. Done. Shortest conversation ever.
5. Bad questions have a “right” answer.
Questions with right answers don’t reveal any new information about each other. They can come across as test questions that can make your date feel uncomfortable. Did the Browns win last night? What’s the weather tomorrow? Who was the 23rd president of the United States? These types of questions all have correct answers; there’s no opportunity to express your personality or thoughts in the answers. Leave these types of questions for Google.
Example: What is the molecular composition of carbon dioxide? “One minute,” turns head: “Hey Google…”
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. This is key. 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.
7 Steps to Develop Genuine Curiosity
Follow these steps to learn how to ask really good questions and electrify your conversations on a date.
1. 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, they’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 scroll Instagram while they’re talking.
2. 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. Repeat words they say to show you heard them.
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 you nod your head and they effervesce.
3. 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 the interviewers?” “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?”
4. 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. I’m curious about it too. Could you share it with me sometime?”
5. 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 b*tch 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. Keep it down to earth. Showing your teeth is neutral and more reciprocal than a stoneface.
6. 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 they went to a hibachi grill with their friends and the chef launched a shrimp into their friend’s shirt. You ask, “Ha! What did April do?” Your date smiles to themselves, enjoying the fact that you remembered their friend’s name.
7. You read the room.
Before speaking, 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 go deeper and when to back away.
Example: You’re in a restaurant, sitting across from your date. You’ve asked eight questions, but they keep giving you one-word answers or the dreaded I’m-not-fine “It’s fine” response. Give it a beat and share something light and humorous, the more self-deprecating the better, i.e., “I need to run to the little boy/girl’s room or I’m going to need a change of pants.”
In the end, if you follow these steps to possess genuine curiosity and avoid asking bad questions as outlined above, your dates will have interesting, naturally flowing conversations, like a rivulet dribbling through boulders.
Go forth in confidence.
You’ve got this.
Dave
P.S. Play Party Qs under the table if you get stuck.