70 Questions to Ask Before Entering a Serious Relationship

These are important questions to ask before entering a serious relationship because they help you find the right person for you and to ensure that you too are prepared for the relationship.

Questions to ask before entering a serious relationship
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Just before you enter a new relationship, here are some serious questions you must ask your partner first. And if you are already in a relationship and things have gotten pretty serious between you both, it’s not too late to ask these questions.

Yeah! 70 questions is a lot. But you don’t have to do these in one single day. Take your time, explore the relationship with your partner, and hopefully, you get to understand your partner and their intention towards you in the relationship.

These 70 questions will help you get a better understanding of where the relationship is heading, and also help you understand how to be more compatible with your partner. So, sit down, take your pen and paper (or notepad) and note down these questions for your relationship partner.

Questions to ask your boyfriend (to-be)

In this section, I assume you are the woman in the relationship (the next section will feature questions to ask your girlfriend or girlfriend-to-be). These apply if you are just beginning to consider him as your boyfriend or if you are already in a relationship with him.

1. Are you ready to enter a relationship?

This will help you understand if he is interested in a serious relationship or if he is not ready for one.

2. Where do you see yourself in the next five years?

This will also give you an idea about what he plans for his life if he plans to settle down soon. You want someone who has plans to settle down if you are eager to get married soon enough too.

3. What do you want out of this relationship?

I expect that you have already started things with him before you ask him these questions. If you have not gotten anywhere with him yet, a better question would be to first ask him if he is in a relationship. If he says no, but he would like to start one soon, then you can go on with him.

By asking him what you want out of the budding relationship you share with him, you gain insights into what his plans for you and the relationship are.

4. Do you wish to get married to your partner soon?

If they are already interested in you, you can be sure they would be thinking about you when you ask this question.

5. How do you see cheating?

He might just tell you the answer you want to hear, of course, anyone would say they hate cheating. But it will signal to him what you feel about cheating in a relationship and make him more cautious if he truly loves you.

6. Why did your last relationship end?

This question makes you know some of the things that put him off totally and avoid doing them.

7. What can I do that can make you leave me totally?

This also makes you know his turnoffs.

8. What can you hide from me?

As you get closer, you may want to understand the things he is capable of hiding from you. Of course, you don’t expect him to tell you straight up what they can hide from you but asking this question gives him the feeling that you are genuinely interested in him.

9. How do you think you’ve improved over the last few years?

This shows you are interested in his growth. It stimulates him to keep working on his abilities, and it also makes you know the kind of man he is, to guide you in your decision to settle with him or not.

10. Do you have any secret about your emotional life you can tell me?

Depending on how close you two have become, he might tell you some intimate things he has experienced in his relationship and dating life. It will make you both get closer to each other.

11. How do you deal with difficult situations?

This gives you an idea of his coping mechanisms when he is stressed out or when he is facing a serious challenge.

12. What emotions easily overwhelm you and how do you control them?

Anger, feeling disappointment, extreme happiness, pride, etc, are emotions that can often overwhelm certain people. You might want to know the emotions he battles with and what he does to control it/them.

13. How have you dealt with your emotions while growing up?

It also gives you an idea of how he has improved in handling his emotions over the years.

14. What do you think about your relationships with other people?

It gives you an idea of how much they value their friendship and relationship with other people.

15. Do I make you happy or how do I make you feel?

You want to know exactly what he feels about you. Again, he is going to tell you that you make him feel happy either way but listen carefully to the tone with which he is going to say it.

16. What are your core values?

If you are interested in a serious relationship with someone, you should at least know the values they hold in high esteem.

17. Do you want kids after marriage, how many?

Nowadays, not all marriages lead to childbearing. You should know if they want kids or not, and if that aligns with your own plans as well. Asking most of these questions also has a way of reassuring your partner that you are interested in a long-term commitment with them.

18. Are you okay with what I want to become?

After making him know your ambitions and dreams for life, it is expected that you hear what he thinks about them, especially if you are interested in a serious relationship with him.

He doesn’t necessarily have to be okay with them all, there is always room for some compromise. And you necessarily don’t have to be with him if he is not okay with what you earnestly want to become in your life.

19. What are your views about women?

Someone who is ready for a serious relationship with a woman should not see women as terrible, wicked, or whatever society has tagged them to be. There is no room for biased generalizations.

20. How is your relationship with your parents?

Gives you an idea of his family dynamics, relationships, and how well he relates with his parents and siblings.

21. What is your financial situation?

Of course, you want to know what he does for a living and also get an idea about his financial situation. This is not to measure him up so you can flee from him if he is not doing so well. You simply care enough to know.

22. What are your top priorities and hobbies?

Before he met you, he had other things that mattered to him, his hobbies and priorities. It’s high time you get to meet those too.

23. How important is sex to you?

It gives you an idea of what his sex drive is, and his ideas about sex before and in marriage.

24. What are your political and religious views?

It is equally important to know the political and religious views of someone you hope to get married to in the near future.

25. Do you love me?

This is self-explanatory, although you may not always get a genuine answer to this question. Again, listen carefully to his tone and behavior when he is replying to you. He might even answer “no” but could mean differently, and vice-versa.

Questions to ask your girlfriend (to-be)

Similarly, if you are the guy, the above questions also apply to you. However, here are some additional questions you can ask your girlfriend before the relationship becomes very serious.

1. Are you ready to enter a relationship?

This will help you understand if she is interested in a serious relationship or if she is currently not ready for one.

2. When do you see yourself getting married?

This question also helps you determine how ready your partner is for marriage. The ultimate goal of a relationship is marriage and you need to clearly define that.

3. What attributes do you want in your dream man?

This question helps you to know if she is interested in you, and to also find out how to make her happier in the relationship.

4. What are the things you find very difficult to tolerate?

Asking her about the things she finds extremely difficult to tolerate gives you an insight into the things she detests the most.

5. Is there anything you don’t want anybody to know about you?

Of course, she can only provide the right answers to these questions if she feels very comfortable around you already. It may take a while to achieve this closeness. If she replies to you, it also makes you see how much she has become interested in you.

6. How do you think you’ve improved over the last few years?

Also, this shows you are interested in her growth. It stimulates her to keep working on her abilities, and it makes you know the kind of woman she is becoming.

7. Are you in a relationship?

This should come first, particularly if you are just deciding to take things seriously with her.

8. What is your genotype?

This question applies to everyone, especially those in the malaria belt of the world with a predominance of sickle-cell disease. Sickle-cell disease is a hematological disease that is genetically acquired in a child whose parents both carry the sickle-cell gene (HbS). If you are HbAS, you must ask this question very critically to avoid marrying someone with HbAS too.

9. How was your previous relationship, if any?

You deserve to know, don’t you?

10. Why and how did your last relationship end?

If she had a previous relationship, it is important you know why it ended.

11. How do you deal with boredom, what are your hobbies?

You want to know what keeps her engaged when she is bored. These are important things in her life you should know about. It also gives you an idea of her personality type.

12. What emotions easily overwhelm you and how do you control them?

Anger, feeling disappointment, extreme happiness, pride, etc, are emotions that can often overwhelm certain people. You might want to know the emotions she battles with and what she does to control it/them.

13. Who am I to you?

This gives you an idea of how she sees you. You want her to see you as a potential boyfriend, not a normal friend or brother. You need to ensure that before you move on.

14. Do you wish you are married by now?

Gives you an idea of how urgent it is for her to get married. She might tell you if she feels pressured to settle down for marriage.

15. How do you feel when you are around me?

Makes you see if she genuinely feels great being around you, or if you are just a pain in the ass.

16. What are your core values?

Also, if you are interested in a serious relationship with someone, you should at least know the values they hold in high esteem.

17. Do you want kids after marriage, how many?

You want to know if she feels excited about having children or not.

18. What are your views about sex now and in marriage?

This helps you understand what they think about sex before and after marriage.

19. What are your views about men?

At least, you want to know if she sees you like the rest of the men who she may have tagged as heartless and wicked with no exceptions.

20. How is your relationship with your parents?

Asking about her relationship with her parents help you know how supportive her parents are, and how likely she can obey them. You need as much family harmony as you can get.

21. Are you currently working, what do you do?

This helps you to know what she has been doing to take care of herself.

22. What are your topmost priorities in life?

Priorities define what we believe, do, or do not. You need to know what things she holds priority in her life as these can help you understand what she strongly believes in.

23. How important is sex to you on a scale of 1 to 10?

With 1 being the least, and 10 being the highest. Questions about sex are important because it forms an integral part of every romantic relationship or marriage.

24. What are your political and religious views?

These are core questions you need answers to.

25. Do you love me?

Just like in the previous section above, this question gives you a clear picture of what she thinks about you. Normally, girls often don’t know how exactly to respond to the question of if they love you or not. But if she is interested in you, she will definitely find a way to communicate that to you.

Questions to ask yourself

You don’t get to enter into a serious relationship until you answer these questions about yourself. It is not enough to know about your partner-to-be. You also need to know about yourself, as this will help you make the right choices.

1. Can I handle a relationship?

If you still have doubts or are unsure if you can handle a romantic relationship or not, you need to wait till you are more ready. This is your time to learn by reading or listening to other people.

2. Do I understand the opposite sex?

Many people don’t understand how members of the opposite sex think and behave. You don’t necessarily have to know everything about the opposite sex before you enter into a serious relationship, but you need to know some important things about them.

3. What exactly do I want in my dream partner?

You need to be clear on your criteria for selecting a partner.

4. What are the things I absolutely hate in a partner?

This question helps you define your turn-offs clearly.

5. How tolerant am I of people’s excesses, including my would-be partner?

Tolerance is key to harmonious living between any two people.

6. Do I have the means to maintain a relationship?

A relationship is neither free nor as easy as many people think it is.

7. Can I manage my partner emotionally?

Emotional maturity is required from both partners. Are you emotionally mature to handle your partner?

8. How prepared am I to manage a home, partner, or children?

Those are expected outcomes of marriage, which in turn is the expected end of most romantic relationships.

9. How much am I willing to sacrifice for my partner?

You might find that you are willing to accommodate another person into your life yet.

10. How long from now do I want to get married?

This makes you understand how prepared you are for marriage.

11. What have I achieved in my life and where do I see myself in 5 years?

It makes you keep track of your achievements and reinforce your dreams in your mind.

12. What is my opinion about sex?

Sex is not the most important ingredient for sustaining a relationship. You should not base your entire relationship on just sex.

13. Do I have well-defined core values and boundaries?

What are your core values? Knowing these help you know who you can be with and who you cannot afford to enter a serious relationship with.

14. What do I want in a relationship?

How do you want to be treated in your relationship? You need to establish these so you can look out for someone who would give you what makes you happy in a relationship.

15. Why do I need a partner?

Loneliness, companionship, business partnership, etc, are legitimate reasons.

16. Will a relationship be a distraction?

If yes, then stay away or read the next question below. It’s not worth it.

17. Am I prepared to overcome distractions?

Distractions are sometimes unavoidable but you need to train yourself to be prepared to overcome all distractions.

18. Are there any lessons from my past relationship(s) I should keep?

Of course, your past relationship experiences teach you important lessons you can’t afford to ignore.

19. Is being in a relationship a need or a want?

Needs are extremely important. Wants are optional. Be sure what a relationship is to you.

20. What are my plans to make money for myself?

Every relationship runs on money. If you don’t know that before now, you need to make concrete plans for making money for yourself.

Now that you have seen these important questions you should ask before you enter a serious relationship or before you make your relationship official, here are a few important things you need to know about asking these questions.

You can decide to ask these questions indirectly

You necessarily don’t have to make it a question-and-answer session with a set of written-down interview questions. You can ask these questions in different ways or imply them indirectly.

Also, knowing about your partner does not have to happen overnight or in one sitting. Patiently learn about your partner by asking these important questions one at a time.

Expect honest answers, not necessarily soothing replies

What if your partner provides answers that can hurt your feelings? This can be a major concern.

As stated earlier in this post, not all responses can be interpreted literally. Your partner can mean differently sometimes. But however, you understand the meaning be, take it that way.

No two individuals are exactly alike. What you want may not be hundred percent desired by someone else. This means you must be open enough to accept their answers even if they make you slightly disappointed.

While asking these questions, remember your core beliefs

Not all beliefs are central to our very existence and productivity in life. Your core beliefs are. While asking your partner these questions, you need to keep your core beliefs in mind. And once, you find that they don’t quite align with your core beliefs, you might need to call it quits before it’s too late to do so.

While no two individuals have the same ideologies, you need to see how closely your ideas and beliefs about life are related.

Final words

While there is a lot more to say about important questions to ask before entering a serious relationship, I will draw the curtain here hopefully to entertain some questions from you in the comments below.

I talked about important questions to ask yourself and/or your partner before entering a serious relationship with them or making the relationship official. All of these questions are geared towards helping you settle down with someone that gives you the most joy and happiness, which are in turn the most important goals of every relationship or marriage.

Prosper Yole is a medical doctor, a seasoned writer and passionate blogger. He is the founder of Knowseeker.com. With many years of trials, failure, and near successes in areas of relationship, health, business & entrepreneurship, personal development, and content writing, he creates quality content that resonates well with his audience across the entire internet.

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