21 Questions for a New Relationship – Ready, Set, Ask

New relationships are exciting and scary, like that new roller coaster ride everyone lines up for. You have the butterflies, the giddiness, staring at your phone every night, talking until you fall asleep and convincing yourself you are not sleep deprived in the morning. It is exciting, but it can also be terrifying at times. How do you know if he or she is the right one? How do you not get your heart broken?

Here are a few questions to ask in new relationships to make sure you are both on the same page right from the get-go!


Who Wants to Go on a Hike? 

It may seem so generic to ask your partner about what they like to do in their spare time. It is very important to be in a relationship with someone who enjoys the same things that you do! You don’t want a partner who compromises to do what you love every day or vice versa. If you workout just to impress her, or if you go on a hike just to make him like you, it will not last. When you both do what you love, but together, it will be all the more fun. Not to mention, you will naturally be doing it for as long as you enjoy it; it won’t be short-lived just to please. Take the time to find out what it is that your partner enjoys and see if it lines up with what you like to do. 


The Awkward Past

While it might be awkward or uncomfortable to ask about past relationships, it is important to know why they did not work out. The past is in the past. But, the past can also offer insightful information. Did it end because either of you want something that the other cannot give? Is your partner afraid of commitment? Are you the right fit? 


K is for…

Let’s blurt it out. Kids! I mean, don’t use as a conversation starter. But, couples often find themselves facing crossroads a couple of years down the life when they have to choose between kids/no kids and someone they love. This can be a big one for some people, especially if you are a very pro or anti having kids. Before you get super attached, make sure you are on the same page. 

Next: 150 Questions for Couples; Get to Know Your Partner


Top 3

Not all questions have to be scary and serious. Sometimes, fun questions can bring you closer and can make your relationship more intimate. For example, asking your partner what are his or her favourite qualities about you can make you open up to one another more. It can connect you and it can be a fun game. “what are 3 things you like most about me?” 


Love Languages

Most people are Savvy when it comes to love languages these days. If you’ve never taken the quiz and you don’t know your own love language, even better! It can be a fun exercise to do together. But, more importantly, understanding your partner’s love language will help you understand how you both show and like to receive love. Acts of Service, Words of Affirmation, Physical Touch, Gifts and Quality Time. Go find out what yours is.


Let the Festivities Begin!

You may be crazy about Halloween and all things scary and your partner might think Valentine’s day is a very important day. In a new relationship? Ask your partner about their favourite holiday so you can make it special and avoid miscommunication in the future. 

Next: 20 Topics To Talk About With A Girl


Do you Like Space?

We all deal with conflict and negative emotions differently. We often treat others how we like to be treated and not how they like to be treated. But how are we to know if we do not ask? Some people like to be hugged and coddled when they are down, others like some space for a few hours or a day. Ask your partner about his or her needs, and be attentive. 


Your Goals or Mine

Single or not, we all have a fluid vision of where we want our life to be. Whether be it a vision board, a 5 year plan or a rough picture in our heads. When we meet someone, we often forget that they have their own, individual plans and visions too. Do we fit in theirs? Do we want compatible things? Will they fit into mine? Ask your partner about his or her vision for the future. No need to draw up a future of the two of you. Before we met, how did you see your life two years from now? What is your ideal life? What do you really want to accomplish in the future?



What is your biggest fear? Often times our biggest fears are the cause behind most of our insecurities. Understanding what your partner fears the most will allow you to approach arguments from a place of compassion rather than fight. Understanding your partner’s deep-rooted fear will allow you to comfort him or her and understand not to take certain argument personally and keep the lines of communication open. 


Mirror, Mirror on the wall

Ask your partner about his or her weakness. What does your partner think is his or her biggest weakness, from his/her perspective. It is important to be introspective and to grow and learn from our mistakes. Is your partner too proud to admit his or her flaws? Or is there room for growth? Maybe he is being hard on himself? Maybe she doesn’t want to change her arrogance? See them how they see themselves, and not for a picture you are painting in our head. 

Next: 21 Questions Game


Trick or Cheat

In some deep, dark corner, we all have a fear of being cheated on. Ask your partner if he or she has ever cheated before and why. Are they remorseful? Has it happened more than once? What is their view on this offence? Is It big? Is it forgivable or not? Whatever the answer is, it will make sure you are both on the same page.



Another awkward but necessary conversation to have is one about the future in general. Do not jump into conclusion or ask your partner if they want to marry you. But, do they believe in marriage in general? Is it something you want? It is a very important question to ask, to make sure the relationship is headed towards a common future and an end goal. If one partner has very strong views on the matter, it is important to know you are both on the same page.


Once Upon a time…

Ask your partner about their childhood and their best childhood memories. It is hard to open up and ask about family dynamics in the beginning. But, asking about childhood memories is a nice gateway into family dynamics and familial expectations. 


I Can be Your Fantasy

Nothing is more romantic than bringing your partner’s fantasy to life. Whether a sexual fantasy or a romantic fantasy, ask your new boo about his or her fantasy, one that never came to life. When it’s a birthday or an occasion, you can make it extra special by bringing their fantasy to life. Plus, it will bring you closed!

Next: 100+ How Well Do You Know Me Questions (Couples & Friends)


Magic Eraser

If you can go back in time and change one thing, what would that be? We all have regrets and we all make mistakes. But, things we wish we could change are a sign of growth and a sign of change. Asking your partner about what they wish they could do differently will let you see how he or she is changing and the areas of growth in his or her life. The more you know about your partners fears and goals and aspirations, the better you can understand them in times of conflict and reduce friction and fights. 


Why me? Why now?

It might be hard to answer this one truthfully. But, it is good to ask your partner why is it that they decided to get into a relationship with you? You want to rule out any autopilot behaviour and you want to make sure your partner is not just filling a void or falling in love with an image they have created for you in their heads. Make sure you are choosing a relationship for the right reason and make sure you are actively choosing one another each day. This will allow you to hold space for one another and to never take the relationship for granted. 


What do you Spend too Much Money on?

Finances are one of those things couples do not like to discuss in the beginning. You want to go on dates, you want to have fun and you want to keep things light. But, we all question our partners’ spending sometimes. Take the time to ask them about what they spend a lot of money on. Do they have a secret hobby? Will it be an issue? Are you both big spenders? It might help you know what to expect from the start to avoid getting upset in the future. It can also help you understand what means a lot to them, even if they don’t talk about it. 


Money Makers

Another important question to ask is about his/her job. Do you love your job? Is it just a way to make money? Most unhappy people are unhappy about their jobs. If you spend most of your day doing something that you hate, you will never be happy in your life. Be realistic, we all hate certain aspects of our job. But, is your partner truly happy? Do they need a little extra support? Are they due for a change? Deepen your bond by digging deeper into your partner’s dreams and desires. 


Dive Under the Sheets

It doesn’t matter what you ask. Just make sure you are both comfortable talking about Sex! It is important to communicate your needs to one another. Make a fun game out of it, but ask your partner about what he or she likes underneath the sheets. Sexual Frustration can be a cause for many arguments. Make sure you are comfortable and open with one another in talking about your sexual needs. 

Next: 50 Intimate Questions to Ask Your Boyfriend So You Fall Deeper in Love


If you Were Stuck on an Island…

If you get stuck on an island, what three things would you want to bring with you? Okay, not exactly an island. But in this island of life, what are the three most important things in your life right now? Not people, not goals, but three things. Learn about your partner’s current priorities. Is working out their holy grail and special time that you need to take seriously? Do they love painting so much and you can expect that to take a big chunk of their time and money? Are they addicted to social media? Believe what they tell you!


Keep it Green

If you were a tree, what tree would you be? Random? Yes! But, that is the point! Keep it light, ask fun questions, be lighthearted. Laugh together, at silly questions and silly answers. Don’t take yourselves too seriously all the time. Have fun, always. 


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How To Tell If A Guy Likes You Over Text
50 Questions to Ask Your Boyfriend
75 Questions To Ask Before You Get Married
20 Things to Talk About with Your Partner
20 Questions Girls Are Afraid To Ask Guys

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