"Okay, we've established we can laugh together, but is this a real partnership or just a great happy hour?"

I've wondered the same thing about how to move forward once the ice is broken and some level of comfort is there. How do you move the conversation to understanding if this person is actually compatible with your future?

The secret to intentional dating is knowing when and how to transition. The basics definitely still stay: you always need to ask at least a few icebreakers and build comfort first. You can’t jump straight to the heavy topics!

But once you've done that, the goal is to ask questions that are still fun to answer but contain hidden insights into a person's values and outlook. This time, the mission is: "What does this person value and how do they look at life or the future?"

It's all about moving from the shallow end to the deep end gently.

Here is your guide to asking the deep questions early in the dating journey to ensure you invest your time wisely.

Value Questions to understand People

1. What's an opinion you’ve changed in the last year or two?

Reveals their capacity for growth and change. Gives you an insight into how they form new beliefs.

2. What’s a skill you picked up just because you thought it sounded cool?

Reveals their curiosity and openness to pick new things. You can ask if that's something they continued or a phase.

3. What's your comfort ritual when you have a really bad day?

Reveals their coping mechanisms, self-care, and primary way of recharging. If it moves forward, you will know how to comfort them when they are having a bad time.

4. What’s the best compliment you ever received, and why did that specific one stick with you?

Reveals what personal traits they value most in themselves. Is it intellectual, physical, emotional or something else?

5. What’s the best gift you ever received?

Reveals whether they value material objects, thoughtful gestures, practical usefulness, or an experience. Gives you a better understanding of love languages and what brings them joy.

6. If you won a small lottery, what’s the first thing you would buy, whether it’s small or big?

Reveals their immediate financial impulse: do they prioritize fun, a small luxury, paying off a debt, or investing?

7. What is a specific thing you will always spend more money on because you think quality matters?

Reveals financial priorities and what they genuinely value (quality coffee, food, travel, home, or specific experiences.

8. If you could take a sabbatical for a whole year, what would you do?

Reveals their passions and definition of fulfillment outside of their job title.

9. What's something you were really good at, surprisingly, because you honestly thought you wouldn't be?

Reveals their self-perception, overcoming self-doubt, hidden talents, and confidence in their capacity to learn new things.

10. What's a common, small, everyday thing that just instantly ticks you off? (Like people chewing loudly or being chronically late)

Reveals their patience level, what boundaries they find easily violated, and their communication style when mildly irritated.

11. What was the last debate or heated discussion you had with a friend or colleague? (No need for details, just the topic!)

Reveals their intellectual interests, what issues they are passionate enough to argue about, and their style of engaging in disagreement (are they measured, or passionate?).

12. If you were ruling the world, what’s one strange or funny law you would immediately set up?

Reveals their unique priorities, their sense of humor, and what minor societal annoyance they would prioritize fixing (a great insight into their worldview).

13. What's a ritual you started just for yourself? (Like a birthday trip, Sunday brunch, or a specific monthly habit)

Reveals how they prioritize their time, their friends, and their self-care. Ask: "Is that a solo ritual, or is it mandatory shared time with a specific group of people?"

14. If you could give one piece of warning or advice to your 20-year-old self about dating, what would it be?

This reveals lessons learnt or something they used to worry about too much or acquired wisdom.

15. What’s the fastest way to get you to apologize?

Reveals their philosophy on accountability and conflict resolution, focusing on the speed and mechanism of repair (do they need a minute, or are they quick to admit fault?)

The Art of Knowing Them

This list is your superpower! Unless their answers trigger one of your absolute Non-Negotiables, don't jump to conclusions too early. These questions are tools for understanding, not judgment.

The mission is simple: Both of you need to know each other to move forward. So, don't keep it one-way; share your stories about yourself as well. Go out there, be curious, and enjoy the adventure of truly getting to know who they are as a person.

Ready to dive into Intentional Dating?

Are you ready to skip the endless swiping and find people who are just as ready for real conversations about their values and future?

Meant2Bae is built for the intentional dater. We help you move past surface-level talk faster by matching you based on shared non-negotiables and values. We believe your time is valuable, and finding a meaningful connection shouldn't feel like a guessing game.