Questions to ask on the first date

Choosing the right person to love you and be your teammate in life is one of the most important decisions you’ll ever make. Dating can be fun and exciting, but it's also the gateway to something deeper. So how do you make those first dates count? By diving into questions that will help you uncover if this person aligns with your values, goals, and dreams.

Often, we can get so caught up in the surface details: evaluating things like if they have the “right” job, look, height, or taste in music, or spinning out over whether they like us, if they’ll call, or when they’ll set up another date. Or perhaps we find ourselves dreading showing up solo at the next wedding or life event, wondering if this is the year we find that special someone.

All too often, we forget to focus on the most important part — how we feel about them and if this person truly aligns with our long-term vision. To make dating a little less confusing and ensure you're on the right path, here are some insightful first date questions to help you evaluate whether this person could be a real match for you. Let’s get into it!

1. What Do You Love or Admire About Yourself?

Self-awareness is so attractive, and it’s something to prioritize when you’re looking for the right partner. This question offers a window into how they view themselves and the qualities they value. Someone with a healthy sense of self-worth will be able to recognize and appreciate their own strengths.

Why It Matters: In a fulfilling relationship, both people need to have a foundation of self-love. If your date struggles to answer this, it may be a red flag, or it might just indicate they aren’t used to thinking this way. Pay attention to their response, but also see if they ask you the same question — curiosity is key!

2. What Does Your Dream Day Look Like?

This question helps you get a feel for what brings them joy and what makes them feel alive. Are they the type to wake up early, hit the gym, and have a productive day, or do they prefer slow mornings and flexibility? Knowing what someone considers an ideal day gives you insight into whether your lifestyles are compatible.

Why It Matters: Compatibility goes beyond attraction; it involves lifestyle and habits. If you’re a go-getter who loves planning and they’re more spontaneous, that’s not necessarily a dealbreaker. But understanding these tendencies early on can make navigating future dynamics easier.

3. What Are Your Top 3-5 Values?

Understanding someone’s values early in the dating process is essential because it’s the foundation upon which strong relationships are built. Values shape how we view the world, make decisions, and interact with others.

Why It Matters: Shared values provide the glue for a lasting relationship. Ask yourself if you can align with what they stand for — even if some values differ, are they complementary? This is also a great question to reflect on before dating: what are your top values?

4. What Was Your Childhood Like? What Is Your Relationship with Your Family?

Our family dynamics often shape our relationship behaviors. Understanding their background can give you insights into how they might handle relationships, challenges, and communication. You’ll also learn a bit about the potential role family might play in your life if things become serious.

Why It Matters: Healthy family relationships, or at least positive reflections on family history, can suggest emotional maturity. Be mindful that everyone’s story is unique, and a challenging past doesn’t mean they aren’t ready for a healthy relationship. Still, it helps to know what has shaped them.

5. What Are You Looking for in a Relationship?

Being clear about intentions on a first date is crucial for avoiding misunderstandings. If they’re seeking a committed partnership, great! If they’re just looking for something casual and that’s not what you want, then it’s better to find out early.

Why It Matters: When you’re dating with the intention of choosing the right partner, clarity is everything. Mutual expectations make it easier to build something meaningful. This question also opens the door for a candid conversation about relationship goals.

6. What Are Your Goals and Dreams for the Future?

Learning about someone’s ambitions and life goals can help you assess whether their path aligns with yours. Their answers can show you if they’re goal-oriented, content with where they are, or just starting to explore their potential.

Why It Matters: To build a meaningful relationship, you’ll want to be sure your dreams can coexist. If you’re dreaming of a life abroad and they’re committed to settling down in one place, those differences could become a challenge down the road.

7. What Do You Enjoy Doing in Your Free Time?

Shared interests are a bonus, but what matters most is that they have things that make them feel alive and fulfilled outside of a relationship. Knowing their hobbies and passions can help you understand how they might spend their time and give insight into their personality.

Why It Matters: We tend to thrive in relationships where both people feel empowered to pursue their interests. Does their idea of fun align with yours? And if not, are you comfortable with the differences? This question helps you understand that balance.

Now the next questions might not be something you ask on the very first date, but they are nonetheless very important to cover early on.

8. What’s the Most Important Thing You’ve Learned from Past Relationships?

This is a deeper question that can reveal a lot about a person’s emotional intelligence, self-reflection, and growth. By asking this, you’re inviting them to share lessons they’ve learned and how they’ve applied these to better themselves in dating and beyond.

Why It Matters: Everyone has a past, and how they view and learn from it is crucial. Someone who can reflect and take accountability is likely to be emotionally mature and ready for a meaningful relationship. It also opens up space for you to share your own insights.

9. How Do You Handle Conflict?

Conflict resolution is an inevitable part of any close relationship, so understanding how they handle conflict can be telling. Are they communicative, calm, or avoidant? Their approach to conflict can give you insight into whether they’d be a supportive partner during tough times.

Why It Matters: No matter how much you connect, disagreements are bound to happen. Knowing how they handle conflict will help you gauge if your approaches align and if they’re equipped to manage challenges healthily.

10. What’s Something You’re Grateful for Right Now?

This question might seem simple, but it’s actually quite revealing. Gratitude often signals emotional well-being and maturity. Plus, their response can tell you a lot about what matters most to them in life.

Why It Matters: Gratitude and a positive outlook often go hand-in-hand with emotional resilience. You’re seeking a partner who can find joy even in simple things and who values what they have. It’s a lovely way to end your first date conversation on a positive note, too.

Make Dating More Meaningful

Dating can be an opportunity to connect deeply with another person if you approach it intentionally. These questions encourage meaningful conversations on first dates and can help you identify whether someone is genuinely compatible. Remember, choosing the right partner takes time and patience, but with the right approach, you can confidently navigate dating and move closer to finding someone who’s a great fit for you.

If you’re ready for dating to feel easy and aligned with your goals of a lasting relationship, join the waitlist for my 3-month mentorship program, Radiant Relationship Academy.