Center for Shared Insight, PC

Dating Differently: Asking New Dating Questions

May 10, 2021
Posted By: Kristen Hick, Psy.D.

It’s easy to be on auto-pilot when you are meeting someone new. There is likely a list of questions you ask without even thinking ranging from “what do you do for a living?” to “where did you grow up?”. While these questions might give you surface-level or basic information about a person, maybe even based on a mental checklist you have about what you are looking for in a partner, they don’t really provide information that can truly help you make a decision about this potential partner’s compatibility and shared values.

In working with clients at Center for Shared Insight in Denver, Colorado, we are encouraging them to ask different dating questions in an effort to help them date in a new way. These questions get more at the heart of your curiosity about another person and go below the surface, including whether you have aligned values, a similar vision for the future, and even compatible coping strategies. 

Consider asking new dating questions on your next first date or early in a new romantic partnership to help you think differently and gather new information about your potential partner. Here is a sample of the types of questions we recommend in three key areas that you can sprinkle into the initial conversation.



What are three things that make you feel fulfilled in life?

What helps you know you are in a good place for a serious relationship?

What is a favorite childhood memory and why?

What is your dream job and why?

What app do you use most on your phone?

If you won $100,000, what would you do next?

How do you spend your free time - with family and friends, engaging in hobbies, volunteering or traveling?


What is your love language? How do you prefer to give love and how do you feel loved?

What are the top three traits you are looking for in a partner?

If you are upset or stressed what do you need or do?

What does your perfect day look like?

What would a good friend of yours say about you? What qualities make you a good friend?

Do you consider yourself an introvert or an extrovert? Do you know your Myers Briggs results or any other personality assessment results?



What three things happened in your life that make you who you are? 

What do you enjoy but are too embarrassed to admit?

What unexpected event or plot twist has been significant in your life?

What is your ideal vacation agenda? Weekend agenda?

What are three things on your bucket list?

What’s your favorite indoor and outdoor activity?

If you meet someone online, it’s easy to include these questions in a fun way during your initial dialogue. Ask them a “fun question” and then give them the chance to do the same. Or, you can make light of this approach on a first date and say “I bet you are tired of answering the first typical 20 date questions and I promise to make you think outside the box” before initiating a new and more meaningful first-date dialogue.

At Center for Shared Insight in Denver, Colorado, we work with clients who are exploring ways to meet romantic partners in new ways or interested in different approaches to get to know them. Dating outside the box and thinking differently about dating by asking new questions and taking in new information is often a turning point for couples who feel like online dating or dating in general just isn’t working

If you can relate to these feelings, contact our team to learn more about how we can support your dating journey through therapy.

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