40 dating questions to take things to the next level

Relationships

Feb 11

Written By Calm Editorial Team

Clinically reviewed by Dr. Chris Mosunic, PhD, RD, MBA

Dating someone new and hoping to deepen your connection? These 40 dating questions can help you build closeness, trust, and explore a possible future with a special someone.

If you’ve been in the dating game, then you know the way it can go sometimes. You’ve been seeing someone for a few weeks or months, and you’ve covered all the basics: favorite ice cream flavor, childhood memories, extracurriculars from high school, foods you like or hate… So now what? Maybe the conversation starts to stall, or you just want to go a little deeper, but how?

As you progress from newly dating to the early stages of intimacy, asking the right questions can help move things forward and take you from two acquaintances getting to know each other to people building a real emotional connection. As an added bonus, it can help you gauge if they’re someone you could see a life with. How reflective or open they are, how accountable or trustworthy they seem. Going deeper allows you to truly know someone and be known by them.

Not sure what kind of questions you should be asking? Don't worry, we’ve got you. This list of thoughtful questions can help you explore the connection and determine if this blossoming relationship could turn into something more. They’re also meant to facilitate conversation and be fun. Afterall, dating should be a delight, not a chore. Let’s dive in.

Can asking certain dating questions lead to love?

While asking the right questions doesn’t guarantee you’ll fall in love with someone, they can support connection, a key ingredient of love.

When you and your date share personal thoughts and feelings, it may make you feel more understood and more bonded. But more than that, honesty when discussing deeper topics helps you both determine whether the connection could be meaningful for you.

Do you share the same morals and values? Does this person seem like they could fit into your life? What would they bring to the table for you, and what would you bring into their life? These are all things that a great question can help you discover.

40 dating questions to ask to help build your connection

Here’s a list of 40 questions you can ask the person you're dating to help you take things to the next level. There’s no need to force these questions into a conversation or put the person on the spot as if they’re being interviewed.

Instead, find ways to work them into the flow of chit-chat, or be forthright and ask if you could trade off asking a few questions as a fun date activity. Just be sure not to overwhelm them with all 40 at once.

The questions start on the lighter side and move steadily toward deeper, more serious topics. Feel free to choose ones that feel appropriate to the level of intimacy you’re sharing with your date.

Questions that help you feel more comfortable

Feeling at ease with someone often comes from small, everyday pleasures and how you recharge emotionally. These questions are designed to surface what brings you comfort, joy, and a sense of freedom, as well as how you balance closeness with alone time.

What’s something that always makes you laugh?
What’s your perfect Sunday look like?
What’s your favorite comfort show/movie?
What’s an activity that makes you feel most free?
How do you like to feel comforted when you’re down?
How much alone time do you need each week?
Who inspires you?
What are some of your hobbies?
How do you feel about being outside in nature?
What album or book would you take with you to a deserted island?

Questions that reveal what matters to you

Values can show up in the everyday details of dating — how time is spent, how appreciation is shown, and what starts to wear on you over time. These questions are meant to clarify what makes connection feel meaningful to you, what you enjoy (or don’t) about dating, and which behaviors help you feel valued rather than overlooked.

What are your love languages?
What makes time spent with someone feel like quality time?
What part of dating do you love/hate the most?
What’s a quality you admire in your friends or family?
What actions make you feel appreciated?
Are there any actions or behaviors that leave you feeling taken for granted?
How do you feel about asking for help?
Are you comfortable with vulnerability?
What is something people misunderstand about you?
What’s something in your life you’re working on or working towards?

Questions that help you understand each other

These questions focus on how you give and receive care, handle conflict or misunderstanding, and balance closeness with the rest of your life. This way, a potential connection is built with clarity rather than assumptions.

What is your relationship with your family like?
How important is your career to you?
How do you relax and unwind?
How do you split your time between dating, friends, work, and solo time?
How do you tend to handle conflict?
How do you stand up for yourself if you’re not being treated fairly?
What’s something that’s challenged you lately?
Do you have any big dreams (personal or professional)?
What is something valuable you’ve learned from dating or past relationships?
Are you comfortable talking about ex-partners?

Questions that explore where things could go

These questions are the ones you work your way up to. They’re designed to help you dive deeper into the potential of the future of the relationship and discuss some topics that are important, even if they can feel a little nerve-wracking to bring up.

Where do you see yourself in five years?
How do you see us fitting into each other’s lives?
Is it important that we align on political or spiritual beliefs?
How important is a commitment like marriage and family to you?
What are your feelings on monogamy?
How do you feel about discussing money and financial goals?
How do you feel about cohabitation before marriage?
What does a healthy long-term relationship look like to you?
What would signal to you that we’re ready to meet each other's friends/family?
Are you comfortable being physically affectionate in public?

Dating questions FAQs

What if these dating questions feel awkward or forced?

Awkward moments can happen when conversations move beyond familiar topics, especially early in dating. Sometimes this simply means the timing is off or the question is a stretch for the moment.

Other times, discomfort can be more informative. It may point to a topic one of you isn’t ready to explore, a difference in expectations, or an emotional reaction on either side that needs a little space. Paying attention to how you feel in the moment, along with the other person’s tone and body language, can offer helpful clues.

If awkwardness passes quickly, it’s usually just a cue to shift topics. If it keeps returning, slowing down or naming the pause may be more helpful than pushing through.

What are some romantic questions to ask your partner?

Romantic questions often work best when they focus on how a partner experiences love and care. They can explore what helps someone feel chosen in everyday life, or what kind of affection feels good to them.

Some examples might include:

“How do you like to be shown care?”
“What are your love languages?”
“How much communication do you like in between dates?”
“How much alone time do you need each week?”
“How much connection do you like each week?”

How do you build emotional intimacy in a relationship?

Emotional intimacy grows through repeated experiences of being heard, respected, and responded to with care. This includes honest communication, follow-through, and the ability to repair after misunderstandings.

Questions can help open these conversations, but intimacy depends on what happens next, including how people listen, respond, and act over time.

What are some fun dating questions?

Fun questions can help get conversations flowing in new relationships without adding pressure. The answers can also offer a glimpse into someone’s personality and what makes them happy.

Here are some fun dating questions you can ask:

What’s your ideal day off?
What’s a movie or show you can rewatch anytime?
What’s your most controversial food opinion?
What’s a small thing that always improves your day?
What’s your go-to comfort meal?
What’s something you’re oddly good at?
What’s a hobby you’ve always wanted to try?
What’s a trip you still think about?
What’s a song that instantly puts you in a better mood?
What’s a harmless hill you’ll die on?
What’s your favorite way to spend a Friday night?
What’s the best thing you’ve bought for under $20?

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Calm Editorial Team