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Writer's pictureA.M. Willoughby

Questions to Ask Yourself Before Taking Your Relationship to the Next Level

This post is the second in my mini-series on questions to ask yourself to reflect on your relationships. Check out last week's post for questions that you should ask when a relationship ends or when you experience a disappointment.


At the Beginning

You do not go through breakups without first entering a relationship. I will be the first to admit that some (a lot) of my relationships have not lasted more than a date or two. In some cases, we did not even make it that far. Some people might say that my lack of “official, long-term relationships” disqualifies me from talking about the subject.


You do not have to take my advice if you do not think I know enough to give it. But, before you make that judgment, let me tell you why. The reason that I have not had a string of intense relationships is that I do a lot of reflecting before I get into a relationship too. I decided a long time ago that it is better to be single than to wish that I was, so I do not get into a serious relationship unless I know it will be worth the time.


I ask myself a lot of questions when a relationship ends to learn from it, and I ask myself many different questions before I get into a relationship to make sure that it has the potential to be the kind of relationship that I really want. Every relationship is a risk, and no amount of self-reflection will protect you from every heartbreak. But, you can save yourself a lot of time if you go into relationships with wisdom and understanding.


So, I am also going to recommend a few other questions that I recommend asking before you get into a serious relationship. I recommend thinking about these questions for yourself and then discussing the topic with your potential partner. Just like the breakup questions that I posted last week, I am sure that these can be modified to fit a variety of new situations, such as a new job.


For the sake of clarity, I do not think you need to ask all of these questions before you agree to go on a first or second or third date with them. If you are still getting to know another person, you will not be able to answer many of these questions.


When I say ask yourself these questions before you get into a relationship, I mean ask yourself these questions before you “define the relationship” or start making commitments to the other person. Some of them may be questions that you need to return to once the relationship has gone further. You could also ask these questions before you get ready to move to the next stage of a relationship, such as before you decide to get engaged.



1. Are you ready for a serious relationship? Do you have any unresolved feelings about an ex or any instability in life circumstances that may prevent you from committing to the relationship?

2. What do you like about this person?

3. Are there any deal-breakers you need to discuss? Have you talked with this potential partner about kids, religion, politics, or finances?

4. What is the goal of the new relationship? Are you both on-board with an eventual goal of getting married? If not, you need to discuss any hesitations you may have.

5. Who do you want to call when something goes horribly wrong? Is your potential partner someone that you can talk to about intense emotions? Can you be vulnerable to them?

6. Who do you want to call when you get good news? If it is not your potential partner, why not?

7. Are there any parts of your personality or past that you are hiding from this person? Why? A relationship will not work if you feel like you have to be on your best behavior all the time.

8. Do you understand each other’s non-verbal cues? How do you know what the other person is feeling in certain circumstances?

9. Do you know this person’s love language? Do they know yours?

10. What bothers you or annoys you about your potential partner? Are you willing to deal with those things for the sake of the relationship? Does the good that you like about them outweigh the bad that annoys you?

11. What would you change about your potential partner if you could?

12. Does your potential partner have qualities that you were looking for in a partner? What are they?

13. What have you learned about yourself while spending time with this person?

14. Whose opinions are influencing your decision to get into a relationship? Do you trust their advice?

15. Have you seen each other in a variety of situations? Do they act differently around coworkers, friends, or family members? Have you seen them get drunk or angry? If they act differently in various situations, do you like all of the different versions of them?

16. Do you know what is essential to each other in relationships? Do you want the same kind of relationship?

17. What makes this relationship better than or different from all the rest? What will convince you to fight for the relationship when things get hard?

18. How will your baggage from past relationships affect this relationship? Can you communicate about those things?

19. Is there anything that you need or want that you are not currently getting from the relationship? Can you communicate those things to your potential partner?

20. How deeply do you trust your potential partner? Do you only trust them when things are going well? What are the circumstances that might cause a lack of trust?

These are a lot of questions, and some of them are things that people who have been in a committed relationship for many years may not have thought about. In my experience, very few people are willing to think this thoroughly before they make relationship decisions.


But, I can also tell you from experience that you can save yourself a lot of heartbreak if you take the time to reflect on these things before taking the next step in your relationship. Asking these kinds of questions has enabled me to have deep conversations at the beginning of a relationship before things get intense and mistakes get made.


The beginning of a relationship is typically a honeymoon phase. When you are in that phase, everything feels perfect and wonderful. You need to know that the relationship will still work when the excitement of new beginnings has faded. These questions will help you to take the blinders off so that you can really understand what the relationship will be like when the honeymoon phase is over.



If you take the time to reflect on these questions for yourself and then talk to your potential partner about some of them, you will start the relationship on the right foot. You will be able to understand each other’s baggage and habits. You will be able to address any potential issues before they begin.


I promise that your relationship will be so much stronger once you have reflected on and talked about these things. Whether you are starting a new relationship or you want to strengthen a relationship that you are already in, these questions can be a game-changer.

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