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Don't make things awkward!

Got a Valentine’s Day first date? Here are the questions to ask to make a second date more likely

  • The Covid-19 pandemic might mean you’re dating over Zoom, but in person or virtually, a first hang-out can be awkward
  • Remember this is a date, not an interview; be interested, not aggressive, and get to know each other

Valentine’s Day may be a little different this year, but you if you’re single, you still might have plucked up the courage to ask somebody out.

In person or virtual, first dates are hard. There’s no denying that. From the endless supply of sweat that you didn’t know your body could actually make, to the awkward silences when you actually contemplate talking about how unseasonably cold it is outside, 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.

The 9 worst things to talk about on a first date

Now, we all hope that the conversation flows naturally on a first date, but inevitably, most of us will be stumped at some point or another. Rather than running off to the bathroom to plot your next conversation topic (been there – it’s stressful), it’s a good idea to have a few questions in your back pocket just in case the humming of the heater 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 are you studying?” or “What do you do?” (perhaps the most boring question in the book), you could ask, “What made you decide to study medicine?” or “How do you enjoy your job as a reporter? I imagine it must be very rewarding.”

The first question allows your date to simply say, “medicine,” but the other two require a bit more thought and introspection, leading to a more thoughtful conversation … and perhaps a second date.

Five questions to ask yourself if you want to date a friend

Other questions that might come in handy:

What do you generally like to do after class/work?

What made you decide to apply to your university/move to the area, and do you enjoy it?

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

I’m just getting into podcasts and could use some recommendations. Do you have any?

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!)

10 quick tips for a guaranteed swipe right, every time

It’s best to stay away from the stereotypical interview questions like, “What is the hardest thing you’ve ever accomplished?” or “Tell me about a time where 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!