21 Questions for a New Relationship

young couple talking while sitting on floor of their new apartment — Getty Images

We've all been there. You know, the experience around a new relationship, marked by late-night conversations that linger until sleep intervenes, both reluctant to just hang up. You find yourself reading endless reviews on Yelp for new restaurant recommendations and trying on multiple outfits until you land on the perfect look for your next date. This stage, typically referred to as the “getting to know you” phase, is generally accompanied by mixed emotions and the excitement of the unknown.

But, let’s also talk about what’s left once you know how your partner likes their coffee or their favorite movie of all time. How do you figure out the meat and potatoes (values, core beliefs, and outlook on life, to name a few) of a person that truly contributes to the longevity of a relationship? Or, better yet, what are the steps required to produce a deeper, emotional connection in the early stages of dating? The answer is simple: Being intentional and asking open-ended questions is a great place to start.

More specifically, playing the 21 questions game—a playful activity designed to help couples explore new territories—is one way to help cultivate a strong foundation for the curve balls the future may throw. After all, the more individuals understand their partner's thoughts, feelings, and daily pressures (all of which can be discovered via the game), the smoother it becomes to build a long-lasting connection.

Meet the Expert

Dr. Shaakira Haywood Stewart, Ph.D. is a licensed psychologist and published researcher based in New York.

Ahead, we put together a simple guide to playing the 21 questions game, in order to help you understand the deepest parts of your significant other. Read on for more.

The Importance of Asking Questions Early in a Relationship

According to licensed psychologist and published researcher Dr. Shaakira Haywood Stewart, "When we are able to be emotionally available and emotionally exposed, we are able to feel a connection with someone. We are able to experience their world a little bit more and that draws us closer to them.”

Keeping Dr. Stewart's words in mind, thoughtfully crafted questions are able to help partners open up and be "emotionally exposed," which, in turn, encourages curiosity, deepens emotional bonds, wards off insecurities, and promotes healthy communication skills. Simply put, asking questions early on is the best way to learn about the person you're interested in, and will help you assess whether or not you'd like to spend the rest of your life with them.

How to Play the 21 Questions Game

At the start of the game, you and your partner must establish that you're both entering a judgment-free zone. (This will ensure a safe space where you both can speak openly.) Next, block out all external distractions so you and your significant other can actively listen to one another once the game begins. This includes putting your phone on silent, turning off the TV, and entering a room where you can hear minimal outside noise. Lastly, figure out how you'd like to select the questions. Do you want to take turns choosing questions from a list? Or would you rather blindly draw each question from a hat?

Another rule? While you can certainly ask as many questions as you'd like, try and ask a minimum of 21, no matter how difficult the conversation gets. Also, keep an open mind and be completely honest. This game is meant to help you and your partner form a deeper connection, so don't be afraid to be vulnerable and speak from the heart.

Below, here are 35 questions to choose from (select 21) that range from family morals to love languages and expectations.

01 of 35

What are your top five childhood memories?

Getting to know your partner's childhood experiences not only strengthens your bond, but it allows you to appreciate the journey that has led them to where they are now.

02 of 35

How are your core beliefs an essential part of how you live your life?

This question provides you with some immediate insight into your partner’s religious beliefs, if any, and worldviews. This also enables you to identify potential differences and understand what impact they may have on your relationship. For example, while political views are a hot topic, it is better to rip the band-aid off instead of tip-toeing around or making assumptions.

03 of 35

In your family, what holidays are most cherished and why?

Battling your future in-laws for your annual Christmas Eve party? I think not. Finding out what traditions are held dearly in your partner's family will give you an idea of what scheduling will look like in the future. This will also help avoid any potential disagreements and allow you to be proactive with your time.

04 of 35

Do you see yourself in a parental role?

Deciding whether or not to have kids is a significant decision that should be discussed early on. If you or your partner envision a life without dependents, relishing numerous nights at your favorite restaurant, it's important to address this preference sooner rather than later.

05 of 35

It’s a warm Saturday afternoon and your schedule is completely open, what are three potential activities on your wishlist?

Downtime in adulthood is a true luxury we don’t talk about enough, and how someone spends it can tell you more than you ever expected.

06 of 35

Do you set personal and work goals? If so, how do you manage this?

Goal setting is a positive quality in a partner and can highlight whether or not they have clear plans for their future.

07 of 35

What are some signs that let you know your emotional cup is running low?

Self-awareness in a relationship contributes to better communication, time management, and overall less stress.

08 of 35

How do you manage a healthy work-life balance?

Here's to prioritizing working to live rather than living to work. In every strong relationship, both partners need to know when to leave work at the office.

09 of 35

Are there any gender roles you believe in?

Laundry, taking out the garbage, and paying bills have long been associated with traditional gender roles. Understanding your partner's perspective on this matter can shed light on potential future scenarios you may encounter.

10 of 35

If you had complete financial freedom, how would you spend your time?

Besides obviously spending time making you a priority, this question lets your partner explore what truly brings them joy and motivation. Use this as a bonding tool, and maybe even gather some gift hints for their next birthday.

11 of 35

What are three accomplishments you are most proud of?

Who doesn’t love to share their achievements? This is a great time for your partner to brag about themselves while you step back and give them their flowers.

12 of 35

What was the hardest life lesson you learned as an adult?

Sometimes we’re fortunate enough to learn life lessons early on, helping us avoid some crazy roadblocks. Other times, we just ignore that sound advice from our parents and it’s not until we are knee-deep in adult life that we find ourselves learning the hard way. Explore these lessons with your partner.

13 of 35

Have you ever been in therapy or have explored the idea of it?

Therapy is now more accepted, moving away from its previous taboo perception. People are seeking support from licensed professionals not just to address personal obstacles, but also as a proactive step. Aligning with your partner on this subject could prove beneficial in the future.

14 of 35

How do you deal with stress?

Regrettably, life isn't always as comical as an episode of The Office, and stress is a common aspect we all have to deal with. Nevertheless, knowing how your partner handles it can work out to your advantage when facing challenges in your relationship.

15 of 35

When was the last time you were wrong in a situation? How did you handle it?

Listen, we get it. Who wants to be wrong? However, we all have to accept defeat sometimes, and how you handle it speaks volumes about your character. So go ahead and find out how your disagreements will end.

16 of 35

What are some pet peeves you just can’t ignore?

From the cracking of knuckles to uncontrollable snoring, some pet peeves are just too much for someone to accept. Go ahead and dig deep to find out if you’ll be investing in some Breathe Right strips or putting separate rooms on the table.

17 of 35

How do you deal with insecurities in a relationship?

Building trust in a relationship doesn't happen instantly, but it's a crucial element that cannot be overlooked. By putting in the work early on and showing an honest commitment to your partner, you can address potential insecurities related to outside connections or when it comes to intimacy.

18 of 35

Who's your favorite musical artist?

Understanding your partner's music preferences can say a lot about their personality.

19 of 35

When was your last relationship and what did you learn?

In every relationship, whether romantic or not, there are interactions between adults where both individuals should gain new insights. If your partner hesitates to open up or doesn't take full responsibility for issues, make a mental note to delve deeper at a later time.

20 of 35

How can I be the best partner in this relationship?

Instead of assuming what your partner needs from you, go ahead and just ask. This eliminates any confusion and shows that you are fully invested in doing your part in the relationship.

21 of 35

What brings you joy in moments of sadness?

Discovering what brings joy to your partner is like uncovering their kryptonite. During difficult times, remember this exchange as a way to bring much-needed light and positivity.

22 of 35

What do you believe are the keys to a successful and healthy relationship?

Encourage your partner to move past generic answers, such as "trust, honesty, and open communication," by requesting them to describe different situations that represent a strong and healthy relationship.

23 of 35

How significant is physical intimacy and do you have any specific expectations in that area?

Physical intimacy builds trust, releases stress, and ultimately allows couples to connect on a deeper level. Laying out realistic expectations will avoid frustrations and the potential to wander, finding connections elsewhere.

24 of 35

How would you handle a situation at work where you were asked to execute a task that went against your morals?

Every day, individuals rely on their values to guide their choices in life. Understanding whether your partner is ready to risk their job to uphold their principles shines a light on their priorities and beliefs.

25 of 35

When and where do you most feel like yourself? Why?

Everyone has their special place. It can be a cute corner cafe, undiscovered by TikTok, or the sounds of the ocean on the warmest spring day. Once your partner has answered this question, safely tuck this information into your pocket for a later thoughtful surprise.

26 of 35

Imagine you were trapped in a TV show for a week. What character would you be?

Does your partner spend the week expressing blunt opinions like Larry in Curb Your Enthusiasm or handling crises like Olivia Pope in Scandal? If anything, this question gives you a glimpse of how your Netflix and chill days might unfold.

27 of 35

If you were having a dinner and could invite five celebrities, who would you invite and why?

The ‘why’ is important here. As an outsider getting snapshots of a celebrity’s life, what qualities does your partner admire? This will help you understand the values they appreciate in others and is an overall fun way to talk through a fictional scenario…unless your partner happens to be Beyoncé.

28 of 35

When it comes to crossing off daunting tasks, do you tend to procrastinate or tackle them right away?

Would all my Type A personalities kindly step forward? If your partner tends to leave tasks to the last minute while you prefer immediate and organized completion, alleviate your stress by obtaining all the details beforehand. This way, you can stay occupied by rearranging your linen closet for the hundredth time.

29 of 35

If you bumped into yourself five years ago, what advice would you offer that would be beneficial today?

Apart from the desired Mega Millions numbers and stock investment tips, which we all wish for, this question prompts your partner to self-reflect on past choices and errors. Engaging in thoughtful and deliberate reflection helps in understanding what worked and what didn’t, which can be beneficial when applied in your relationship.

30 of 35

You’ve been asked to plan the ultimate vacation and then document your experience. Where are you going?

Whether you guys have already experienced your first getaway together, or it’s a future idea, this question can help you uncover your partner's travel preferences. While you may be envisioning bellinis and sandy shores, your partner could be more interested in hitting the slopes in Zermatt. Either way, it’s a fun question to get the conversation rolling.

31 of 35

What is your love language?

Knowing the small gestures that bring your partner happiness not only strengthens your bond but also gives you a little cheat sheet on how to go the extra mile. So go ahead and plan a special date night at home or surprise them with a lunch delivery at the office.

32 of 35

Do you participate in any community service? If not, would you be open to joining a project?

Being a well-rounded person involves recognizing the value of dedicating time to support others. If neither you nor your partner is engaged in a community service initiative, this could be a wonderful chance to connect while making a positive impact on someone in need.

33 of 35

How would you define your personal style and what do you think it says about you?

Having a partner whose personal style complements yours is always a bonus. Whether it's a simple, clean vintage t-shirt paired with Levi's or any other combination, confidence is the ultimate accessory when entering a room.

34 of 35

You are in charge of planning an ideal date. Where are we going and what would we do?

This is your time to discover your partner's thoughts. Feel free to express your perspective by joining in and giving some constructive feedback. After all, if a beach sunrise is on the fictional agenda and getting up before 6 a.m. is absurd in your world, let it be known.

35 of 35

Your mom calls while we are in the middle of dinner to say that she’s cleaning out your childhood room and needs you to come over immediately. Are you cutting the date short or asking her to wait until the morning?

Prioritizing relationships with people you love is only uncomfortable if you do not set clear boundaries. Use this scenario as a gateway to discuss more about managing relationships with people you both value.

How to Have Better Conversations With Your Partner—Especially If You've Been Together Forever

How to Play the 21 Questions Game to Strengthen Your New Relationship