Dating Advice

How to Handle Awkward First Date Questions

What would you do in the following situation? You are on a date with a new
person. You feel like you are in the hot seat because this person is attentive
and asking you lots of questions. You’re trying to make a good impression, you
want to put your best foot forward and you may be required to answer, or at
least be asked, some questions you’d rather not discuss.

How do you handle this? Let’s go through a multiple choice!

Choice A: (This really isn’t a choice it’s a reaction to being put on the spot
and it happens to lots of people) You become flustered, and defensive. You
stammer something about feeling uncomfortable or overheated and you turn red in
the face and become completely tongue-tied. This is not your best option.

Choice B: (Another body reaction to uncomfortable situations) your brain
freezes and you glance around for the easiest and fastest escape route and you
bolt for it. In this case you will not be asked out for a second date. If you
are asked out after the bolting episode your date is either very forgiving of
rude behavior or desperate for company.

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Choice C: (Used when you are aware and prepared) you pause for a moment and
smile. Not letting the other person see your discomfort. You keep your voice
even as you say, “That’s an interesting question, could you clarify that some
more?” This will give you time to think and also allow your date to re-evaluate
what he or she just asked. You could also turn the tables on the person asking
by asking a question of your own, “Do you always ask such probing or intimate
questions so soon after meeting someone for the first time?” This will usually
disarm the other person and also alert them that they stepped a tiny bit over
the line with you though you’re not really offended, just not interested in
answering that particular question.

Being put on the spot is not comfortable and usually sends us into a tizzy of
embarrassment. It doesn’t have to be that way if you can develop a few of the
following skills.

  • Stop! Don’t react or speak for a moment.

This will give you time to think and also to gain your composure back.
Sometimes when confronted with silence during this pause the person asking the
question will feel uncomfortable for asking and quickly rephrase the question
without you having to answer it. The biggest mistakes we make in social and
business situations are when we jump in with dialog before thinking because of
nervousness. Use a pause to think, breath and allow the other person to do the

  • Clarify the question.

This gives you a chance to make sure you are certain of what they are asking
and also gives you an extra minute to formulate an answer. Let’s say the
question was “What didn’t you like about your last job?” or, “Why have you
never married?” Both of these questions are ones that can be upsetting and
difficult to answer graciously. It the case of the job, you don’t want to make
yourself or your former employer appear to be hard to get along with. In the
case of why you haven’t or aren’t married, this question is really too personal
of a question for casual conversation and really nobody else’s business. So
repeat the question and add a little to it.


For the question “What didn’t you like about your last job?”
You could pause, smile and ask, “Do you mean as far as the tasks I was required
to do or my feelings about the environment?” This will do several things in
your favor:
1. It shows you are really listening.

2. It shows you don’t jump right into an answer without clarification.

3. You remain posed and don’t get flustered easily.


For the nosey date or social question, “Why have you never married?”
Once again, ask for clarification, “Are you asking about my dating history or
my future goals?” This will once again make the person asking stop and think
about whether or not the original question was appropriate and then saves them
from offending you; also it saves you from saying something you wouldn’t in
normal circumstances.


  • Use an evasive answer.

No matter what the question is, my favorite reply when feeling like I don’t
want to answer or that the question is not appropriate is, “That’s an
interesting question. Do you ask all your dates that?” Or, “Fascinating
question, I’ve never been asked that before. What do most people say?” These
comments can save you from making the wrong comment right off the bat and may
provoke the asker to elaborate on what they really want to know. Also by asking
if the person asked all their dates these questions you can find out how many
people your date has in the Rolodex!

Many people don’t really think about what they are saying before they speak and
ask questions that can make the other person feel uncomfortable, put upon or
down right embarrassed. I don’t think they do this to offend or hurt generally,
I think they don’t really know how they come across or that the question was
inappropriate or offensive. If you can learn to subtlety instruct by using the
above skills you will not only come across as confident and poised, you will
have a much better time and enjoy your budding relationship without acquiring
horror stories to tell.

Try these techniques and I guarantee you’ll feel more comfortable, you’ll sweat
less and also impress!

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Shawna Schuh

Conquer Apathy and Erase Rudeness as you follow proven, fun and beneficial information by Shawna Schuh, CSP. Specializing in communication, professionalism, service & business finesse. Shawna helps you bring your best self to the work you do for maximum results. To book Shawna to speak visit

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