21 Questions for a New Relationship

Relationship Rules
04 May 2023
16 min read
New Relationship? Start Asking Questions!

A long time ago, kids played a game called 21 Questions. One person thought of a famous person, a common object or an animal. The players had a total of 21 questions to ask to figure out the answer. Since then, there appeared lots of variations of “21 Questions,” including those with “adult” topics like starting a new relationship.

Related reading: Dating vs Relationship – What Are the Main Differences Between Them?

In all the glow and affection, a new relationship may seems like this could really be “it” right away. If that’s your case, step back and take a breath. Do some critical thinking. You have a new partner, and you want things to turn into a healthy relationship. But healthy relationships are based on far more than what you are experiencing right now. You have to get to know your partner at a deeper level.

What you need to determine as you move forward in your new relationship is how compatible are you in all aspects of your lives. If your new relationship is going to move into a serious one, it’s going to require more than just the current relationship energy of being totally infatuated with each other. After all, for a new relationship to move forward, the two of you need to be on the same page regarding important things. Ask these 21 questions for a new relationship to check if you’re ready!

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21 Questions for a New Relationship: 8 Ways to Ask Something Personal

1. Were You the Golden Child, the Black Sheep, or Something in Between?

This should get your new partner talking about their family dynamics growing up – relationships with parents and siblings especially – and give you some insight on whether this person will “fit” your idea of a healthy relationship. Do you like someone who is a bit of a rebel, craves excitement and new experiences, and doesn’t follow a traditional path, or are you looking for a calmer, more standard lifestyle (or something in-between)?

2. How Do You Spend Your Alone Time?

The answer to this question will tell if you are on the same page in some important areas. If they spend their time on social media and playing video games, but you prefer spending it reading, painting, or on other projects you can do by yourself, then you may not be as compatible as you’d like. Not a deal-breaker, but it does have some importance.

3. How Do You Deal with Conflicts with Friends and Co-Workers?

This answer will give you insight into their ultimate approach to conflicts with you. Are they rigid? Do they lack the ability to see the other person’s side and work toward a compromise? A person who needs to be right and who is unwilling to admit mistakes is probably not someone you will want to spend the rest of your life with.

4. Where Will You Be 5 Years from Now?

This is a typical job interview question, but it works for new relationships too. You want to understand what goals this person has. It not only speaks to their ambitions but to what they value in their professional and personal lives. If money is the only goal, it’s good that you know that now. If that’s a big goal for you too, then maybe you are a match.

Personal new relationship questions

5. What Person or Cause is an Inspiration for You?

Your new relationship partner should have a “hero” or at least some cause that inspires them to do more with their life than just go to school or work, play, and earn money. If they have a person or cause that inspires them, you will get a better understanding of what’s important to them and what may motivate them to go beyond the mundane activities of life. This will provide an interesting conversation if you also answer the question. And if you are impressed, you may be on your way to a growth-oriented relationship.

6. What Do You Do During Your Free Time with Your Friends?

Among these 21 questions for a new relationship, this one helps to get a handle on non-work interests, hobbies, and activities. It’s not that you want to see if these would be things you are also interested in. Couples need to have independent time with their friends. But is their free time spent at bars and clubs? Is that okay with you? Or would you prefer they are involved in other “healthier” activities? Not a deal breaker but it could loom larger in a long-term relationship.

7. What Are You Grateful For?

Here’s a biggie in the 21 questions for a new relationship “game.” Most of us can come up with who and what we are grateful for pretty quickly. Your new partner should be able to as well. If it takes them long to answer, be careful. There should be people and situations/circumstances in their life that have been important in guiding and helping them, and they should have these foremost in their minds. If they have to pause a long time, they are trying to come up with a response that you will be happy with. Not a good thing. Egocentric people don’t have a grateful attitude.

8. What’s Your Idea of the Best Romantic Evening?

The best dates should be special occasions. A more traditional great date for your new relationship may be something like dinner, a movie or dancing. For someone a bit more adventurous, it might be karaoke at a favorite club; for someone into creativity, it might be a paint-and-sip night or an escape room event. Compare their response with your thoughts on the matter.

Fun questions to start a serious relationship

3 Fun Conversation Starters for a New Relationship

9. If You Had to Evacuate and Only Take 10 Things, What Would They Be?

A pretty superficial person will probably choose personal items like their jewelry, their most expensive wardrobe items, and such. Someone whose values go deeper may choose items such as photographs of loved ones. A practical person will grab their laptop, coursework books and notes, etc. What would you choose? Do the priorities coincide? Will be interesting to know.

10. If You Won a Million Dollars, What Would You Do with the Money?

Your partner’s answer to this fun question will give you clues about their core values. Of course, any normal person would spend money on things they want and would enjoy. But if all of the money would be spent on these things, beware. How would you manage such a windfall? If you’re altruistic, it’s important that a potential long-term partner has such view too. It’s called having a balance of values – some self-serving, some in the service of others.

11. If This Were Your Last Day to Live, What Would You Do?

This of the 21 questions for a new relationship is probably more important than you realize. Would this person spend time with family members or others closest to them? Or just take the top item on their bucket list and fulfill it? Would they hold a gathering of some sort to say goodbye – or spend it getting drunk and having sex? Just hear their response to this fun question as they will speak their key values.

5 Serious Questions to See How Deep You Can Connect

12. Are You Still in Touch with Your Exes?

Listen carefully to your partner’s answer on their last relationship experiences. Someone who spends a lot of time trashing their exes is probably a person who is not willing to take any responsibility for failed relationships. This might be a clue that they have narcissistic tendencies. It’s all about them and how they were wronged. But, if your new partner still communicates with exes and speaks well of them, you have someone who sees failed relationships as the result of shared issues.

Related reading: How to Reconnect After a Relationship Break: 16 Tips to Function as a Couple Again

13. How Do You Define Cheating?

This is an important one of the 21 questions for a new relationship to ask your partner. Why? Because you may have very different views. If your partner’s perspective is that it is okay to flirt online or in person with others, as long as it goes no further, you may not be okay with that. If this new relationship continues, you will find yourself jealous and angry, and the relationship will go south on you.

Related reading: Characteristics of a Cheating Woman: Pay Attention
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14. Do You Believe in a Higher Power?

It’s important to get a handle on a possible partner’s spiritual beliefs, especially if your beliefs are important to you. And this is an important way to get to know this person on a deeper level. While you do not necessarily need to share the details of your religious beliefs, the general concept of a higher power can be a dealmaker or a deal-breaker for you.

15. What Are Your Biggest Fears?

Everyone is afraid of something. If you are dating someone who states they have no fears, you may want to reconsider this new relationship. Why? Because this is someone who sees themself as or at least wants you to believe that they are invincible. This can also be a sign of a narcissist – someone who believes that they are the center of their universe and “untouchable.”

16. What Expectations Do You Have of a Partner?

This one among 21 questions for a new relationship can really become a deal breaker, so make sure ask it. This way, you’ll make sure you’ve found the right person among many personalities and personality quirks out there.

There are people who are hugely independent and want lots of space, even in a relationship. They want things to be separate but maybe equal. At the other end are the needy partners who want someone to take care of them and their needs. And then there are the narcissists who insist that they always come first. Unless you are into co-dependency, what you want is a balance that makes up a balanced relationship.

Final questions for a new relationship

The Final Five

The 16 questions above will “test” your new relationship’s personality, behavior, basic values, personal activities, and general personality characteristics. None of them, as you see, relate to romantic relationships or sex. We all have a sensual side, and love and sex are important in a relationship.

So, these last 5 questions will relate to love and sex. Now, you may be hesitant to ask these early on in a relationship but ask them you must as time together goes forward. I you’ve already had a romp or two in the hay, you have a right to know where this relationship is going and what your new partner believes about romance and sex. So, as these intimate questions without fear.

17. What are Your Thoughts on Long-Term Commitments?

This is an important question. If you are moving toward a monogamous relationship, you have every right to know if your new relationship feels the same, at least about making commitments. And a good follow-up to these 21 questions for a new relationship might then be if they are interested in a long-term commitment to you. If not, it’s good to know now.

18. What Are Your Thoughts on Marriage and Family?

It’s perfectly fine for a partner to want to wait before committing to marriage and creating family with kids. And you may actually be in the same place right now. But what about the long-term future? Do you both agree that this is something you eventually want? If you do and they are just not sure, you are risking eventual heartache. Thus, it’s worth discussing what’s significant for both of you in terms of starting a new family.

19. Describe a Sexual Fantasy You Have for Your Sex Life

If they are honest, you will get a glimpse of what you might be doing with them in the future. Maybe it’s a threesome; maybe it’s some kink. Maybe they’ll share something important about their sexual health. Whatever it may be, are you down with it? Maybe you have a fantasy or two of your own. Don’t be shy to talk about it. Share them with your partner and watch for their reaction. You may be surprised how strong your secrets and preferences are in creating a strong love bond between you two.

Related reading: The Making of a Sexual Goddess
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20. What’s Your Favorite Type of Foreplay?

You may have partnered up with an incurable romantic who is into love language and lots of kissing and caressing in the buildup to sex. Or they may be more matter-of-fact. When it’s time to have sex, let’s get it done. What’s important to you? Don’t think that you will be able to change your partner’s behavior in the future to meet your needs. Just make sure you can love what you hear and see.

21. What’s More Important – Sex or Romance?

This is a really tough question to answer, even for yourself. Probably the best answer here is that romance and sex go hand-in-hand. Sex is the natural result of people in a healthy romantic relationship. Sex without romance is just a hookup and a physical act of biological need. Make sure you are on the same page on this one.

When to ask new relationship questions

There You Have It…

These are 21 questions for a new relationship will help you dig into the inner workings of a new partner. But you may have more than this. These questions are good conversation starters but don’t give you the whole picture you want. But if you going to make a deep future commitment, you have the right to ask the deep questions that are most important to you.

When you want more, do not hesitate to ask them. After all, there are things that will be important to you in a committed relationship that are not covered here. So, playing 21 questions for a new relationship can be a fun start for a conversation before you ask those relationship questions that really matter to you.

Some Tips as You “Interrogate” Your Partner

Any relationship question can go horribly wrong if it’s asked in the wrong setting or at the wrong time. So set some ground rules for yourself as you probe your partner’s beliefs, priorities, future goals, deep relationship questions, favorite music, greatest talent, or even a favorite guilty pleasure. And then go and ask.

Ask When You Are Spending Quality Time Together

Questions for a new partner should not be asked in a social environment that includes others and a “party” atmosphere. Is this the time for a key question such as what is your ideal partner? Hardly. When you ask a personal question, you need to be in a climate that is personal. These are not for date nights that include large groups of friends.

Never Be Judgmental

It’s important that you keep an open mind as you listen to what they reply. If you become judgmental or critical, they will shut down – and you will never really get to know them more as you are moving forward.

Be Forthright with Your Answers

You must be willing to share the same information about yourself that you are asking of this new person in your life. New relationship questions cannot be just one-sided. Your life should be just as much an open book as you are asking their life to be.

Don’t Overload in One Sitting

Of course, you want to know everything as soon as possible, and you are impatient for the answers. But you need to find a healthy balance between just enjoying their company and getting the info you want. If you pepper the conversation with what you think are the most important questions to ask, they will feel like they are in an interrogation room.

This is never a good beginning if you expect to develop a new romance. The most important thing is that you are gradual in your investigation, and your attempts to know your partner are in understanding what makes them “tick.” One date night or two, even though intimate, cannot accomplish this.

Prioritize the Right Questions to Ask

Do you really want to know the one secret they have never told anyone? Chances are you won’t get an answer anyway. You need to prioritize your questions based on what is most important for you to get a sense of their ideas. The little things can wait until things start to gel.

The important things to ask your partner in the early stages are the significant ones that give you insight into their family dynamics, core values, essential beliefs, and passions. Make a list if you must, so that each question helps you get a clear sense of who you are hooking up with. Does a difference of beliefs matter? Then you have to determine if it is a deal-breaker.

Don’t Discuss Commitment in the Beginning

If you ask questions that “force” this someone to discuss commitment very early on, you are likely to scare them off. The most beneficial approach is to gradually move up to this serious talk of relationship types as you move forward to a more serious level in a new relationship. You need to get to know this person before you get to the deep communication. Have a good time, stretch out the 21 relationship questions, and give it time.

Give Your New Relationship a Try

Playing 21 questions for a new relationship will definitely increase your understanding of a new partner’s lifestyle and all of the things they value. Just be certain that you strategize how you will be asking your questions and be prepared to answer them yourself so the conversation is not a one-way discussion. There is no one thing that will make or break your relationship; there is no one right question to ask. Over time, you will get to the truth to see if you are a match.

Love&Sex Expert
Cherie Hamilton
I’ve always been inspired by women who are outgoing, very sure of themselves, and not afraid to be who they were, including their sex lives. Under their tutelage, I gradually shed my old self, hung out and socialized with them, and, over time, became the empowered, self-confident, and sexual woman I am today. Happy to share my insights with other women today!
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