First Date: Answer in the Form of a Question – GTJ Dating Series with Erika E. (No. 60)

quiz-graphicWhat are some questions you can ask on a first date?

First dates are hard.  There’s no denying that.  From the endless supply of sweat that you didn’t know your body could produce, to the awkward silences when you actually contemplate talking about how unseasonably cold it is outside (Snowquester, anyone?), to the question of who pays the bill, first dates are often fairly anxiety-inducing.  One thing that makes it even harder is not knowing the right questions to ask.

Now, we all hope that the conversation flows naturally on a first date, pinging and ponging like Zhang Jike in the London Olympics.  (Yes – I’m a total ping pong nerd!)  But inevitably, most of us, even those who think we could have a conversation with a piece of broccoli if we had to, will be stumped at some point or another.  Rather than running off to the restroom to plot your next conversation topic, it’s a good idea to have a few questions in your back pocket just in case the gulping of your drink doesn’t quite overpower the dreaded silence.

There are certainly no right or wrong questions to ask on a date, but the ones that have the most luck require more than a simple one-word answer.  You want to get the person thinking, showing them that you actually care.  For example, rather than asking, “What do you do?” (perhaps the most boring question in the book), you could ask, “What made you decide to get into exotic bird-watching for a living?” or “How do you enjoy your job as a (fill in the blank) analyst?  I imagine it must be very rewarding.”  The first question allows your date to simply say, “I’m a _____,” but the other two require a bit more thought and introspection, leading to a more thoughtful conversation… and perhaps a second date.

Other questions that might come in handy:

–          What do you generally like to do after work?

–          What made you decide to move to the DC area, and how do you enjoy it?

–          How was your day?  (Often overlooked, but a great conversation-starter.)

–          What kinds of things do you like to read for pleasure?  Have you read anything good lately that you would recommend?

–          What would be your perfect Sunday?

Remember that this is a date, not an interview, so try to avoid acting like you’re judging the other person based on his or her answers.  (Maybe you are, but keep that to yourself!)  It’s best to stay away from the stereotypical interview questions like, “What is the hardest thing you’ve ever accomplished?” or “Was there ever a time that you were challenged to do something you felt was wrong?”  These questions are scary, whether at an interview or a date.  Don’t put the person on the spot.  Rather, ask something that he or she already knows or can at least have a fun time thinking about.

Dating is about both talking and listening.  The date should be a give and take, with you asking some questions and your date asking some questions.  What you say is just as important as your ability to listen.  And what will you be listening to?  The answers to these fabulous questions you’ll ask!

Erika Ettin is, as the Washington Post has noted, a “modern day Cyrano.” She is the Founder of A Little Nudge, where she helps people with all aspects of online dating.  Check out her interview on NPR here. An archive of all of Erika’s columns is also available.  Want to connect with Erika?  Join her newsletter for updates and tips.

5 replies
  1. Erika
    Erika says:

    Dear Annoyed Reader,

    Thanks so much for your feedback, and I’m sorry you feel that the dating advice in my articles isn’t for you. Agreeing to disagree is what makes the world go ’round. The advice I give has proven success for both men and women. What I love about my job is that there are often different ways to do things, and sometimes people may not agree with every piece of information… but the majority of people do. (They, unfortunately, just don’t comment as readily.)

    Best of luck,

  2. Annoyed Reader
    Annoyed Reader says:

    If you’re thanking me for my feedback shouldn’t you also let readers view the points I and others have made? I saw at least one comment by another reader which criticized your article, and it was deleted too.

    Thanking me for my feedback and then denying people the opportunity to read is more than a tad insincere.

    So it’s your call. Do you want to open up the discussion? If so, I look forward to it, and readers can draw their own conclusions. If not, be honest about the amount of dissent you’ll tolerate, and let readers draw their own conclusions regardless.

  3. Rachel
    Rachel says:

    I am a GTJ administrator. The reason the comments were taken down was not because they were negative about the article, but because they were outright disrespectful. We are happy to have people express their opinions, in a constructive and respectful way.

  4. Annoyed Reader
    Annoyed Reader says:

    Dating advice is powerful, so anyone who gives it should accept the huge responsibility that comes with it. Anyone who charges money for it should hold themselves to an even higher standard.

    At the risk of being accused of disrespect, let me provide a response to Erika’s advice. I’ve removed my point by point reasons why I question her judgment, so hopefully this is agreeable enough for the website.

    If the question “what do I say on a date?” is something in your mind, it’s probably because you never figured out how to flirt, tease, or talk to the opposite sex in a different way than you would your boss. If you’re in that spot, work on fixing that. Memorizing more interview style questions will only make the problem worse.

    I don’t think about what questions I should ask on the date, because questions just come up in the natural flow of conversation. That said, if you do need to put some notes into your smart-phone as a backup, here are some more interesting alternative’s to Erika’s.

    If you look up Chuck Klosterman’s questions to ask on dates, they’re out of left field, but at least they’re new and interesting. It provokes a discussion where your date doesn’t have an automatic response cued up. That’s emotionally engaging. Frankly, playing a game of “Never Have I Ever” would at least bring out some colorful stories. Check out the game “Loaded Question” where you have to guess people’s responses to outrageous questions. You might be able to lift a few from there.

    Any of these are infinitely more interesting than trying to be guy number 992 to ask “So what made you move to DC?” Don’t get me wrong, you have to ask that question eventually, but it should be a quick filler between all the other fun you bring to the date.


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