Life Advice



Erika Ettin: Less-awkward first dates start with the right questions

Erika Ettin, Tribune News Service on

Published in Dating Advice

First dates can be, well, uncomfortable sometimes. There’s no denying that. From the sweat coming out of pores you didn’t know existed, to the awkward silences when you actually contemplate talking about how unseasonably cold it is outside, to the question of who pays the bill (a never-ending conversation), first dates are often fairly anxiety-inducing. (They can also be wonderful, of course!)

One thing that can make it even harder is not knowing the right questions to ask. Now, we all hope that the conversation flows naturally on a first date, but inevitably, most of us — even those who think we could have a conversation with a brick wall — will be stumped at some point or another.

Rather than running off to the restroom to plot your next topic of conversation, it’s a good idea to have a few questions in your back pocket.

There are no right or wrong questions to ask on a date (though, don’t try me on this…), 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 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 medicine?” or “How do you enjoy your job as a pediatrician? I imagine it must be very rewarding.” The first question allows your date to simply say, “I’m a doctor,” but the other two require a bit more thought and introspection, leading to a more thoughtful conversation.

Other questions that might come in handy:

— What do you generally like to do after work?

— If you weren’t here with me right now, what do you think you’d be doing?


— What made you decide to move to the area? Any favorite things about it?

— How was your day? (Often overlooked, but a great conversation-starter, as long as the other person doesn’t just say, “fine.”)

— Do you have a happy place? (And you can always add your own first so as not to completely put someone on the spot. Mine? Trader Joe’s on a weekday afternoon when it’s not crowded.)

Remember that this is a date, not an interview, so try to avoid acting like it’s a test someone is going to pass or fail. It’s best to stay away from the stereotypical interview questions like, “Where do you see your life in the next five years?” or “Tell me about a weakness of yours and how you overcame it?” These questions are scary, whether at an interview or a date. Don’t put the person on the spot. Rather, ask something they already know or can at least have a fun time thinking about.

On that note, I would also recommend avoiding questions like, “What are your deal-breakers in dating?” and “How soon do you want kids?” Don’t put the cart before the horse — it’s a date. Nothing more, nothing less.

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!

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