10 Meaningful First Date Questions that Spark a Deeper Connection

Nice couple enjoy a cocktail on a date


I think it is safe to say that almost everyone thinks they are great conversationalists. That they know what questions they want to ask their dates. In reality, I find that far too many singles out there really know how to properly engage their dates in a way that is most likely to lead to an authentic connection.

Today, I want to spend some time writing about the seemingly simple, but often underutilized dating tool… “the question.” Spending less time talking about yourself and instead of asking your dates thoughtful and intentional questions not only gives you an inside look at who the person sitting across from you is, but at the same time quickly gauge if the two of you are a good fit.

Sure, there are questions like, “Do you have any brothers and sisters? What’s your favorite TV show? Do you like sushi?” These are all perfectly acceptable questions to ask a date, but there are questions you want to also ask that have a little more emotional bite. Ones that peel back the onion, if you will, of what’s beneath the surface of your date.

The most significant component of these deeper getting-to-know-you questions is that they tend to be open-ended. This means that they require the person receiving the question to expound on their answer beyond a simple one-word answer or just yes or no. Open-ended questions are like heat-seeking missiles that allow you to dive deep into someone’s mind and soul and look around for a while. Because they are so powerful, they tend to either draw you closer to your date or push you farther apart.

Another purpose for asking deeper questions is that they tend to pull out answers that will help you understand if the person you’re dating meets one or more of your Non-negotiables. Non-negotiables are the core values that you must have in a relationship or the relationship will fail.

asian couple drinking wine together

They are not small things like what their favorite song is or what kind of car they drive. Non-negotiables are the deep, substantive building blocks that will make or break any relationship you enter into. Most people have 10-15 of them and they are often center on things like your view family, long-term goals, or how you treat people in your life.

I’d also like to point out that once you ask one of these questions your next task as a smart single is to actively listen. Active listening means that you are engaged with the speaker, paraphrasing and reflecting back on what is said, and withholding judgment and advice. Great conversationalists tend to be great listeners so make sure that as you develop an arsenal of questions to ask your dates, that you make sure to always maintain the ability to actively listen.

Finally, although I am offering up 10 great get-to-know-you questions here, by no means should you ask all 10 in one sitting. Yes, it’s nice to try to get to know someone as quickly as possible so you don’t waste their time or yours, but connecting with your date will be impossible if they feel they are on some kind of job interview or worse being interrogated by the police.

That means you want to plan to pepper in a few pointed questions here, a few there, and prioritize making the conversations flow naturally. So here are my top 10 questions to ask on a date that sparks a meaningful connection.

1. What’s the most embarrassing thing you can remember that’s happened to you? – This may seem like a strange question to ask someone since it could seem you are trying to embarrass them. In reality, what you are doing here is checking to see the person’s vulnerability level. Vulnerability is one’s ability to expose themselves to the emotional risk and step out of their comfort zone.

It’s an extremely important quality to bring to a committed relationship and this question will help you gauge if this is someone who is an open book or someone who tends to conceal unflattering parts of themselves. You want to not only listen to what they say but how they say it. Do they own the story, relish in how it made them feel, or, worse, a story they refuse to tell at all?

2. What would you change about yourself if you could? This question is just another way to gauge ‘vulnerability’ as well as their self-confidence level. But be careful here because both narcissistic personalities and self-assured people may answer that they don’t want to change anything.

It’s your job then to make sure you work to find out which one they are. Conversely, if your dates want to change many parts of themselves it could mean they lack self-confidence and are not comfortable in their own skin.

3. What’s the best advice anyone ever gave you? People who ask for help and listen to others for advice tend to be more self-assured and open, while people who prefer to always give advice often have inflated egos and crave power.

The type of advice you hear from them and who it came from could help you decipher which side of the fence they fall on. Also, if the advice they received tends to contradict what you understand or know to align with your own moral or ethical compass then that too is very good to know.

4. What were you like as a kid? – Although you may not garner too much from this question as people do tend to change for better or for worse over the course of their life, it still will give you some insight into how they view their former selves. If they have poor memories of their childhood there could be some unresolved trauma that has not been dealt with. If so, better to know this sooner than later.

5. Where do you see yourself in 5 years? 10 years? This is a super important question to ask not only because you will quickly know if you and your date are heading in the same direction. For example, if you are someone whose answer would be, “have a family, and kids,” and your date answers, “make a million bucks and travel as much as possible,” then, of course, you are on a collision course to misery.

If the answer is in close alignment with your vision, make sure to ask follow-up questions into any and other areas of their life that may interest you (work, family, where they want to live, etc.) to get the full picture.

6. What is a big challenge you faced and how did you move through it? Life is full of challenges and you want a partner who is not able to face them but does so with confidence and perseverance.

Someone who cowers at the sight of life’s big obstacles may not be able to offer you the security you require in a relationship. This means you want to pay special attention to the challenge itself (the bigger the better, I say), as well as how they were eventually able to overcome it.

7.  What brings you joy? What makes you disappointed? Long-term committed relationships are full of both times of immense joy and unwanted disappointment. This two-folded question will give you some insight into what brings your date up to and what brings them down.

Pay attention to the size of the events that bring affect them. For example, if they find joy or disappointment from things that you might deem as trivial or selfish (i.e. making/losing money or sex) that is a red flag of the highest order.

8.  What qualities do you look for in a long-term partner? What are three red flags you try to avoid? Again, quality life partners are going to have depth, so you want to make sure your date is looking for the core values that truly will help your relationship flourish.

If, for example, he or she only answers with superficial qualities like what the person looks like, the amount of money they make, or the type of music they like then you know what you have.

9.  What’s something you want to learn or wish you were better at? Not everyone has to be on a constant path of personal or professional growth, but it is important that they aren’t stuck in their ways and refuse to learn new things.

You always want a partner who is flexible and willing to learn new things if it will help make their lives better. The best of all answers will not only tell you what they want to learn but that they are someone who loves to learn and are on a constant path of self-discovery and improvement.

10. What’s the one thing that people always misunderstand about you? A great partner will not only understand you but also understand themselves and how the world may view them. We all have flaws and sometimes these flaws (or even our good qualities) can be misunderstood by others. With this one question, you might get some true insight into the inner workings of your date and how they see themselves in the world.

If you have more questions on ways to make a deeper connection, schedule a Free Relationship Readiness Review with me here.