Never the Right Word

Never the Right Word

Scripts & Templates for Life’s Uncomfortable Conversations.

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Dating 101: Fill Awkward Silences With These 5 Questions

The wonderful world of dating is packed with all kinds of interesting people and memorable experiences, but why is it that most people are TERRIBLE at first dates? It’s as though we allow ourselves to get overwhelmed by the pressure and we become these mediocre overly-censored versions of ourselves. That said, with just a tiny amount of preparation you may never have to run out of things to talk about on a date ever again.

When you are out on a date with someone, especially for the first time, it is a good idea to avoid one-dimensional questions that are too factual. Questions like “What do you do for work?”, “Where are you from?”, “Where do you live?”, etc will not tell you much about someone’s true character.

Factual questions will make the other party feel like they are being interrogated by you and honestly, none of these questions are good enough to keep the conversation going. It is better to ask multidimensional questions with which you can take the conversation to so many other places and end up learning more valuable information about someone’s true personality.

Question 1 | Find Out About Their Travel Experiences


What is your most favorite place in the world?

This is a good conversation starter. As a multidimensional question, it will help you and your date to talk about traveling, hobbies, and you will learn some of the things in which they are interested. For example, do they like sightseeing? Or maybe they like going to museums. Maybe they are into physical activities and they like a hike in the mountains, canoeing or maybe diving.

You will be able to learn a lot more about them and their interests by asking this question. Also, it is a safe question that won’t make you or them feel uncomfortable. It is perfectly OK for the first date and it shows them that you are interested in knowing more about them.

Question 2 | Find Out About Their Interests


What is one thing you’ve always wanted to try?

This could be a follow up to the first question to keep the conversation going. People always like to talk about their dreams and desires. But most of us don’t even talk about our dreams or things that we would like to do before we die, like a bucket list. Life always gets in the way or we feel like people we interact with are not interested enough in our thoughts and dreams.

When you ask a question like this to your date, you can be certain that they will be happy that you did. This can take the conversation in places that might surprise you. You might find out that you have much more in common than you thought. Or maybe this person can encourage you to realize your dreams somehow.

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Question 3 | Find Out About Their Loyalty


How would your friends describe you? How long have you known them?

A clever question to find out more about someone’s loyalty and the way they interact with others around them. Think about how long you have known your best friend. 20 years? 10 years? Just a few months? This can bring up more follow up questions like where did they meet? Were they always best friends? Did they always get along? What makes them their best friend?

Talking about these things will tell you a lot about what your date values the most in a friend. What are some of the things that are important to them in a friendship? What are some things they can’t tolerate about others?

Question 4 | Find Out About Their Passions and Their Motivation Level


What are you most passionate about?

There are a few different types of answers you might get for this question. It is a smart way to find out if someone is a workaholic if they truly have a passion, or if they are still trying to figure things out. If your date’s passion is related to their work, it might be a sign that they might not always have time for personal relationships.

It depends on what you are looking for in a date, of course. It might bother some people; it might be ok for others. If they already have a passion and they are following it, it might show that they have a good work-life balance and they are not afraid of following their dreams. They set aside quality time for themselves.

People who set aside quality time for themselves will be better at giving you the quality time you deserve. These people usually have a healthy level of self-esteem. But if they are still trying to figure out what their passion in life is, there might be several reasons for that.

Perhaps they are still young, or maybe they didn’t have enough opportunity to think about it. Maybe there are too many things on their mind and they don’t know where to begin.

Question 5 | Find Out if They Like Learning and Discovering New Things


What is one thing you wish you knew or understood more about?

A good question to ask someone to find out more about what interests them. Maybe the answer will be something you are very passionate about as well and you can share your knowledge with them. Or maybe it will be something you also wish you knew more about and this can allow you to organize more activities together.

When people have common interests, they feed each other and learning from one another brings them closer. Sharing common interests allows us to push our limits and explore new horizons.

Try to avoid asking negative questions like the ones that related to death, loss, negative emotions, and feelings like jealousy, what makes them angry, their regrets, the unhappiest moments of their lives. The list goes on and on. You don’t want to ask questions about their last relationship either, like why it ended, if they still talk to their ex. And it should be a red flag for you if your date is talking negatively about their ex. Avoid personal questions about their income, how many people did they date, if they consider marriage, and having kids. They are intimidating and no-one wants to get into a serious conversation on a first date.

At Never the Right Word, our aim is to give you practical examples of how to handle life’s difficult conversations. If you have an awkward situation that you’d like example templates for, request a topic here.   

If you’re interested in further reading, we’ve also included links to our trusted resources and related posts below. To find out more about NTRW and our recommended tools, you can do that here.  

Lastly, if you found this content helpful or want to share your own examples, let us know in the comments. We’d also be delighted if you shared this article and joined us on social media too!

Never the Right Word

Never the Right Word

Hi there! I’m Amy, and I’m the person behind Never the Right Word. I’m a designer-by-day who’s fascinated by human psychology; you’ll find me learning about what makes others tick through all types of media and good old-fashioned conversation.

In 2019 Never the Right Word was born to fill the gap of ‘how-to’ websites with copy and paste examples showing you EXACTLY what you need to say to steer difficult conversations into positive outcomes.

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