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  • Jill Hinckley

7 Thought-Provoking Questions For Your Next Date.

Updated: Jan 29, 2019



Picture this: You’re sitting down with your date in a beautiful setting. You’re both comfortable, you’ve ordered drinks and you’re ready to let a beautiful evening unfold. So how can you start to get to know your date on a bit of a deeper level?

Sharing a little information about each other’s lives is an important way to build understanding and trust. According to Psychology Today, the number one predictor of a relationship’s success is trust, so building that foundation is essential. While it may feel daunting, we’re here to help. In my years of working with clients, I’ve found these thought-provoking questions to be useful in really getting to know your date, and equally importantly - making them feel heard and understood.

Sounds ideal right? Here are some fun questions. Let’s get started:


What did you want to be when you grew up?

All of us have a connection with our inner child, whether we recognize it or not. Asking what your date wanted to be when they were a child will prompt them to reminisce on their younger years. Not only can this be a catalyst for sharing stories from the past - it’s a great way to understand your date in a new way.


What’s the best advice you’ve ever received?

Sometimes words just stick. This question will help you tap into your date’s life philosophies and underlying values.


What is your favorite quality about yourself?

What you love about yourself, you’re also likely to love in others. Asking your date this question is a great way to get to know the qualities they value. Knowing this about yourself, too, can help guide your dating life.

Where do you see yourself in 10 years?

Is it mastery of a new career or hobby? Is it moving somewhere new? Learning about your date’s 10-year plan is helpful in gauging what their life might look like going forward - and whether that vision is in line with yours.


What is your superpower?

This is a fun one...your date’s answer may surprise you. You might just be sitting across from someone with an uncanny ability to juggle or whip up the perfect bowl of ramen.

What was your most memorable travel experience?

For many, travel is a great way to venture out of the comfort zone. Take a mental vacation as you both reminisce on adventures past. Not only are travel memories fun to share, but you might also just light the spark for a future journey together!


Who are the special people in your life?

Use this question to fast track happy feelings in your date. Whether its children, a group of close friends or a tight-knit mixed family, the people we love make life worth living. Getting to know more about your date’s inner circle is a thoughtful and considerate move.


We want to know - have you tried these out yourself? What did you learn? We welcome your feedback!