10 Questions That Will Make Your Date More Interesting and Fun

Congratulations on taking the leap! You’ve signed up for a dating app that Forbes recommended, and now you’ve received your first few contacts. But after reading their messages, you realize they’re either not a match or just questionable. But here’s the good news: you haven’t deleted the app, and it’s only been 10 minutes! If you're mature and open-minded, maybe you're looking for a dinner date, a companion to talk to, or a potential romantic partner. No matter what you're seeking, one thing is certain—a good conversation will make all the difference.

To help you get started, here are 10 great questions that can spark a deeper conversation:

1. What are three things you can’t live without?

This question helps you understand what someone truly values and what’s important to them in life.

2. Who has been the most influential person in your life and why?

This reveals the people who have shaped their perspective, character, and decisions.

3. What is your most prized possession?

It could be something sentimental, valuable, or meaningful—this question gives insight into what they care about the most.

4. What kind of music do you listen to?

Music often says a lot about a person’s personality, interests, and emotions. This question can lead to a fun discussion about favorite bands, concerts, or shared tastes.

5. Do you play an instrument?

If they do, it might reveal a creative side or an interest in the arts. If not, it could spark a conversation about hobbies or musical interests.

6. Who are your favorite people in your family and why?

This helps you get to know their family dynamics and which relationships they hold dear.

7. What do you do during your free time?

Learning how they spend their free time will show you what kind of activities they enjoy and what keeps them busy when they’re not working or studying.

8. What hobbies or interests would you like to pick up?

This question gives insight into what they’re curious about or things they wish they could explore, helping you learn more about their future aspirations.

9. What do you value in people?

It’s always interesting to hear what someone considers important in their friendships and relationships. This question will help you understand their values and personality.

10. What’s been the most satisfying thing in your life?

This gives you a glimpse into what they consider their biggest achievement or source of happiness, and it may reveal their passions or long-term goals.

The Conversation Goes Well... Now What?

If your conversation goes well and you want to see each other again, but your schedules don’t quite line up, don’t worry! Life gets busy, and it's okay to take things slow. You don’t have to rush the relationship. Keep living your life, stay in touch when you can, and let the relationship grow naturally.

This is just the beginning of getting to know someone, and it’s a great chance to practice your social skills. Don’t stress over the details. Keep your plans simple, and remember, building a connection takes time.

If you're not meeting up as often as you’d like, try becoming friends with several people. Keep things relaxed—take turns paying for coffee or tea, or go Dutch when attending events. You can even travel separately if that feels more comfortable. Don't feel pressured to respond to texts or calls the same day—people used to take weeks to reply to letters, so there's no need to rush!

Ultimately, if you're not enjoying this process, remember: life’s too short. Do what makes you happy and spend time with people who lift you up.

For additional support in relationships call your Christian counselor in Denver at 720-577-5571 or schedule a free 15 minute consultation.