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5 Questions to Ask Your Date to See if You Have a Deeper Connection

Whether you’ve been on a million dates or you’re getting ready for your first one, it’s essential to ask the best questions to get to know your date better. If you’re dating for a long-term relationship that leads to marriage, you need to see if you have a deep connection. But what should you talk about? Here are five questions to ask your date to learn more about them and their vision for their future.

1. What Makes You Unique?

It’s easy to assume things about someone from their dating profile. You can think they have a lot of friends because every profile picture is a group photo. You can assume fishing is their favorite hobby because they used the 🎣 emoji in their bio. But the best way to get to know someone on a deeper level is to ask questions. Get them talking about themselves. This one question creates space for more about their interests, hobbies, and passions.

2. What Is a Childhood Experience that Shaped Who You are Today?

Asking someone, “What was your childhood like?” is such a loaded question. So loaded that it’s easier to give a general answer like, “It was good” or “Pretty average.” But by asking about one specific memory, you’re likely to hear more details about the life experiences that shaped them. This question also opens up more conversation about family, children, and other deep topics.

3. How Has Your Faith Impacted Your Dating Life?

If you use a Christian dating app like Upward, you can assume your date has some type of spirituality. Learning how their faith has impacted their dating life will give you insight into how they prioritize their beliefs in relationships. You can expand this conversation by asking a similar question: “How do you want your faith to impact your dating life?”

4. What Do You Picture When You Think of Married Life?

We all have different views of marriage. Hearing someone’s ideal picture will help you learn more about their hopes for their future. Maybe they picture an adventurous lifestyle with just one another. Maybe they imagine a loud but happy home filled with five kids, two dogs, and a cat. By hearing someone’s picture-perfect marriage, you’ll learn whether or not you envision similar experiences for your future.

5. What is One Thing You’re Proud Of and One You’re Working to Accomplish?

Learning about someone’s successes and aspirations will help you understand their priorities. Continue this conversation by sharing your accomplishments and plans for the future. An important part of a long-term relationship is supporting one another. This conversation will give you a glimpse into what that would look like.

Sure, you can just straight-up ask someone, “What are your hobbies?” or “Do you want kids?” or “Where do you see yourself in ten years?” But the above five questions to ask your date create space for more exciting conversations about these things without it feeling like an interview. Remember, there are no right or wrong answers. There is just an opportunity to learn if you have that deeper connection with your date. Try Upward today and maybe just find that first date.



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