How to Ask Great Questions and Get Conversation Flowing on a Date

Goodbye, awkward silences!
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Goodbye, awkward silences!

First dates are awkward. It could crash, or it could bloom, or it could leave you feeling apathetic. In my case, it was usually crashing. Most of my first dates would have described me as an anxiety-riddled chatterbox. Lulls in conversation would have me blabbering about . . . well, anything. (Face, meet palm.) Some people urge nervous daters to just relax and let it flow, but for me, relaxing into conversation is a whole lot easier when I have some good questions prepared.

“A first date can set the tone for a relationship or it can quickly reveal that no relationship (or second date) should happen,” says Dave Willis, author of The Seven Laws of Love: Essential Principles for Building Stronger Relationships. But you don’t have to let chemistry do all the talking. Willis tells Verily that you don’t have to save revealing questions for date number two. The first date is a great opportunity to take the conversation in a direction that leads to more meaningful and fun topics. “You never want to make your date feel like he's being interrogated, but it's vitally important to ask the right questions right from the start,” says Willis. “His answers can help you both quickly know whether a potential relationship is something you should pursue with one another.”

So how does one go about conversing on the first date to set both parties at ease? Take a few cues from some expert communicators.

01. Do you get nervous on first dates, too?

For me, the problem is my nerves. But clinical psychologist and marriage counselor, Randi Gunther, Ph.D,  suggests letting your date know you are a bit nervous and ask him if he get’s nervous on first dates too.

Dr. Gunther urges me to just “be honest.” She explains that just saying, 'I'm a little anxious when I meet someone for the first time,' could open the door for a shared experience on a first date, or some great ‘first date’ stories to break the ice. Chances are, he will immediately agree and let you know he gets a bit nervous too. If not, ask him what the hardest part about first dates are for him.

This may sound like a bad way to put your best foot forward, but in my case, sharing a little vulnerability actually goes a long way in setting both your date and you at ease.

02. What drew you to your job?

For me, one of the most frustrating parts of first dates is getting trapped in surface level conversation and never getting to anything deeper. Playing 20 Questions can get tedious and only leaves you with a bunch of fun facts about the other person. Shawn Smith, author of Is He Worth It? How to Spot the Hidden Traits of Good Men tells Verily that digging a little deeper helps save the conversation from dying off quickly.

“When you’re first getting to know a guy, don’t dwell on question that generate statistics, like what kind of food he likes, where he grew up, or how many siblings he has. Those questions are fine places to start, but they eventually kill a conversation,” explains Smith.

Smith suggests that we ask open ended questions about what our date thinks, what he feels, or what motivates him. For example, instead of asking your date what he does for a living, try asking him a question like, "What drew you to your work, hobby, or education?" This will help you get to know more about his values, one of the most important factors for long-term relationship success.

“You’ll get a sense of what matters to him when his eyes light up as he talks about his purpose in life,” says Smith. But you’ll also know where you don’t see eye-to-eye.

In my case, digging a little deeper with open ended questions gives my date more time to talk and me more time to listen and be thoughtful about how I move the conversation forward.

03. What’s your theme song?

Let’s face it, we all go into a first date burning to know what kind of man we are sitting across from. But one dinner isn't going to give us all the answers. Still Willis says that talking about art, music, and movies can tell you a lot about your date’s interior life and his personality.

“Talking about movies and music is a very non-threatening conversation starter, but can also reveal great insights into someone's personality,” says Willis. “A person's taste in music and favorite songs reveals more than just his or her playlist; it can actually reveal some things about his or her personality. Are they upbeat? Melancholy? Thoughtful? Playful? Music can help you find out.” 

Instead of asking “what’s your favorite music?” Try asking him something more creative, like “If someone was making a movie about your life, what songs would you want on the soundtrack?” It’s a little cheesy maybe, but you are sure to get some laughs and some insights into his personality.

04. If you had a billion dollars, what would you do?

I can talk too much, but it’s not easy talking to someone who is a little shy or introverted. Maybe he’s nervous too. Asking a light hearted hypothetical can help him to open up about his dreams and aspirations and also help the conversation take a more meaningful and less one-sided course.

Who says you can't talk about money on a first date!? “How a person chooses to spend or invest his or her money says so much about their priorities, goals and dreams,” says Willis. “This could give you a glimpse into his hopes for his future and can let you know if it's the kind of future you'd like to be part of.”  Willis suggests we try asking, "What would you do with the money if you won the lottery?" It could also reveal a ton about his life’s philosophy and purpose.

05. What kind of family vacations did you take growing up?

First dates can feel way too formal—borderline job interview. Asking him question after question can be overwhelming, but giving each other the chance to talk about personal experience, especially your childhood (or where you and your family come from), can bring powerful memories and fun stories to the conversation. "Most people hate being interrogated, especially guys, but all people like to talk about themselves," says Gunther. She suggests asking him about growing up and what his favorite childhood memories were. "When you were small, what did you day dream about, and has that dream come true?" Although my personal dream of becoming a weather girl didn't come true, it would be hilarious to tell him about it, and the path my life has taken instead, and where I hope it will go in the future.

Finally, don’t freak out about asking the perfect questions. When it comes to preparing for a first date, so much energy goes into it: scheduling, picking the perfect place to meet or what to do, the outfit—the list goes on and on. Give yourself permission to relax and be yourself. As Randi Gunther told me, “You don’t know him; you have nothing to lose.” And it’s true. There is so much to discover in conversation with somebody new, so have fun with it.

Photo Credit: Manchik Photography