10 Questions to Ask When Dating

When I was in the early stages of my career as a relationship coach, I had the opportunity to witness an intriguing interaction. At a coffee shop one evening, I watched a young couple on what appeared to be their first date. While they both were visibly nervous, the woman took the initiative and asked her date, "If you could invite three people, living or dead, to dinner, who would they be and why?" It struck me how this single question transformed their interaction. It shifted from surface-level small talk to a profound discussion about values, aspirations, and the individuals who inspired them. From that point forward, I realized the power of the right questions in the initial stages of dating.

First dates can often feel like a job interview, with both parties probing for information to evaluate the potential of a relationship. But they don't have to be this way. With the right questions, you can peel back the layers of your date's persona, fostering a deeper connection and leaving a lasting impression. Rather than sticking to the routine and sometimes mundane, "What do you do?" or "Where are you from?" why not explore new conversational territories that engage both you and your date?

In this guide, we'll unveil ten must-ask questions that aim to spark meaningful conversation and connection. These queries are not only intriguing but also reveal important information about your date's character, life goals, and personal values.

And no, these aren't your typical '20 Questions' game queries. These are carefully selected to strike a balance between light-hearted fun and deeper introspection, avoiding the awkwardness of prying too much, too soon. Whether you're an extrovert or an introvert, you'll find these questions easy to ask and surprisingly engaging to discuss.

So, are you ready to break the ice with ease (and depth!)? Let's dive in!

1. If You Could Invite Three People, Living or Dead, to Dinner, Who Would They Be and Why?

This question is much more than an interesting ice breaker—it's a way to gain a snapshot into your date's inspirations and values. The people we admire reveal what we aspire to be or the qualities we deem important. Whether your date chooses historical figures, celebrities, relatives, or even fictional characters, their answers can offer a glimpse into what they respect and value.

Additionally, asking why they chose these individuals encourages your date to dig deeper into their motivations and aspirations. Maybe they admire the relentless innovation of Elon Musk or the literary prowess of Jane Austen. Perhaps they respect their grandparent's resilience in the face of adversity or are inspired by a character's bravery in their favorite novel. Whatever the case may be, this question can open up a world of engaging and enlightening conversation.

Importantly, this question also communicates your interest in their thoughts and perspectives, which can be an attractive quality in itself. But remember, the goal here isn't to judge their choices, but to understand them. Make sure to keep an open mind and actively listen to their response—after all, the essence of a great date lies not only in talking but in listening, too.

2. What's the Most Adventurous Thing You've Ever Done?

Adventure means different things to different people. For some, it could be hiking up a snowy mountain peak, while for others, it could be moving to a new city with no plans in place. This question not only gives your date a chance to share a memorable life experience but also reveals their level of risk-taking and openness to new experiences.

Asking about your date's adventures can highlight their interests, resilience, and how they handle unexpected situations. Moreover, it can lead to stories that spark excitement and give you a better sense of your date's character. They might tell you about the time they backpacked through Europe, started their own business, or even took an improvisation class just for the fun of it. Such experiences often come with fun anecdotes, lessons learned, and, most importantly, tell you about their zest for life.

But remember, it's not just about listening—it's about engaging. If your date's adventure aligns with your experiences, feel free to share. This common ground can further enhance your connection and show them that you're interested in getting to know them on a deeper level.

3. What's the Best Piece of Advice You've Ever Received?

Asking about the best advice your date has ever received can reveal many aspects of their character and perspective. It demonstrates what they regard as wisdom, what principles guide their decisions, and the life lessons they hold dear. Moreover, it can show how they've grown as a person and how they approach challenges and obstacles.

Perhaps they'll share a pearl of wisdom passed down from a family member, a life-changing tip from a mentor, or a profound insight gained from a book or movie. Whatever it may be, it will offer you a window into their thought processes and priorities. This question not only deepens your understanding of your date but also encourages a heartfelt and potentially inspiring conversation.

Also, keep in mind that sharing a personal piece of advice can be a vulnerable experience. Respond with empathy and respect, and if it feels appropriate, share the best advice you've received in return. This exchange can foster mutual respect and intimacy, solidifying the bond you're beginning to form.

4. If You Could Master Any Skill or Learn Something New, What Would It Be and Why?

This question is a fun way to delve into your date's interests, dreams, and the way they see their future. Whether they yearn to play the guitar, speak another language, master the art of cooking, or learn about astrophysics, their answer can reveal a lot about their passions and curiosities. It can give you insight into their drive for self-improvement, their intellectual curiosity, and their aspirations.

In addition, it opens up a whole new range of topics to discuss. If they dream of learning to paint, perhaps you can talk about art styles, famous painters, or your own experiences with creativity. If they wish to learn coding, you can discuss technology, the digital world, or even the philosophical implications of artificial intelligence. The possibilities are endless.

Remember, as they share their dreams with you, it's crucial to be encouraging and supportive. Show enthusiasm about their interests, ask follow-up questions, and share your own aspirations. This exchange of ideas can create an environment of mutual support and understanding, making your date feel more comfortable and connected with you.

5. What Book, Movie, or TV Show has Significantly Influenced Your Life?

Pop culture and media have a powerful influence on our lives and our perspective of the world. This question invites your date to share a piece of media that has significantly impacted them. Whether it's a life-changing book, a movie that altered their perspective, or a TV show they feel deeply connected to, their answer will provide a glimpse into what shapes their thoughts, beliefs, and values.

Their choice can speak volumes about their tastes, but more importantly, it reveals how they internalize and reflect upon the stories and messages they encounter. Maybe a character's journey mirrors their own, a storyline resonates with their experiences, or a particular theme has shaped their worldview. Regardless, their answer can lead to an engaging and meaningful conversation.

Remember, this question can sometimes lead to a passionate discussion, especially if the book, movie, or TV show holds significant emotional value for your date. Be open-minded, appreciative, and receptive—even if their choice is not in line with your preferences. Sharing your influences can be a great way to find common ground or at least understand each other better.

6. What's One Thing About You That Surprises People?

This question encourages your date to share something unique or unexpected about themselves. It can lead to fascinating revelations that wouldn't typically come up in a casual conversation. Maybe your date is a master at juggling, speaks several languages fluently, or has a unique hobby like beekeeping. This query enables them to showcase an interesting facet of their character, creating a lively and engaging discussion.

Moreover, it gives them a chance to share something they're proud of, something that sets them apart from the crowd. It allows you to appreciate their individuality and the traits that make them unique. Not to mention, their answer might challenge your assumptions about them, adding an element of surprise and intrigue to the date.

Respond to their revelations with genuine interest, and feel free to share something about you that surprises people. This reciprocal sharing can make the date more personal, and the shared vulnerability can help establish a deeper connection.

7. How Do You Like to Give and Receive Love?

While this question may seem a bit forward for a first date, it can be an important one. It's a less direct way of talking about love languages, a concept introduced by Gary Chapman in his book "The Five Love Languages." According to Chapman, people tend to express and interpret love in five main ways: words of affirmation, quality time, receiving gifts, acts of service, and physical touch.

Asking about your date's preferences in giving and receiving love can shed light on their emotional needs and the way they express affection. Perhaps they feel most loved when spending quality time together, or they show love through thoughtful gifts. Their answer can provide valuable insight into your compatibility and how your relationship might develop.

However, approach this question with sensitivity. It's not meant to rush intimacy or commitment but to understand their perspective on love and relationships. And if your date seems uncomfortable with this question, respect their feelings and gracefully shift to a lighter topic.

8. What Does Your Ideal Weekend Look Like?

This question might sound mundane, but it's an effective way to understand your date's lifestyle and preferences. How someone spends their leisure time can reveal a lot about their interests, priorities, and the way they balance their life.

Maybe your date enjoys quiet weekends with a book, prefers adventurous outdoor activities, loves exploring new places, or values spending time with friends and family. Their answer can help you gauge your compatibility in terms of lifestyle and interests. Plus, it might give you ideas for future dates if things go well!

Feel free to share your ideal weekend in return. This mutual exchange can help both of you understand each other better and determine if your lifestyles can complement each other. Remember, though, that different preferences aren't necessarily a deal-breaker. They can also bring diversity and excitement into a relationship.

9. If You Could Change One Thing About Your Life, What Would It Be and Why?

This is a slightly deeper question that encourages your date to share their dreams and the areas of their life they may wish to improve. Their answer can reveal their goals, ambitions, and the values they hold. Perhaps they want to achieve a specific career goal, develop a personal attribute, or build stronger relationships.

Moreover, this question provides an opportunity to talk about personal growth and the willingness to change. It allows your date to be honest and vulnerable, which can strengthen your connection. It shows that you are interested in their personal journey and their aspirations.

However, bear in mind that this question can touch on sensitive issues, so it's important to approach it with empathy and understanding. As they share, be supportive and open, and if you feel comfortable, share something you'd like to change about your life. This mutual sharing can lead to a deeper connection and a meaningful conversation.

10. What's Your Favorite Way to Give Back to the Community or Make a Positive Impact?

Last but not least, this question delves into your date's values, compassion, and their perspective on social responsibility. Whether it's volunteering at a local food bank, mentoring young students, or advocating for environmental conservation, their answer can offer a glimpse into their heart and what they care deeply about.

Not only does this question help you understand their philanthropic inclinations, but it also uncovers shared values or interests that can create a stronger bond. Perhaps you both are passionate about animal welfare or value education for underprivileged children. Recognizing these shared values can contribute to a more profound and meaningful connection.

As they share, remember to express appreciation for their efforts and share your ways of giving back. The exchange of ideas can also inspire new ways for both of you to contribute to your communities and make a positive impact.

As we conclude this guide, remember that the best conversations are a two-way street. While these questions can spark engaging and insightful discussions, it's also essential to actively listen to your date and respond thoughtfully. The ultimate goal is to understand each other better, find common ground, and build a meaningful connection.

At the end of the day, dating is about exploration—discovering new people, learning from them, and enjoying the journey. So, the next time you're on a first date, remember these ten questions and let the conversation flow. Happy dating!

Resources:
1. Chapman, G. (1992). The Five Love Languages: How to Express Heartfelt Commitment to Your Mate. Northfield Publishing.
2. Tannen, D. (1990). You Just Don't Understand: Women and Men in Conversation. William Morrow and Company.
3. Gottman, J. & Silver, N. (1999). The Seven Principles for Making Marriage Work. Harmony.