170 Questions to Ask Yourself About Your Relationship

Asking yourself the right questions about your relationship can be like flipping a switch in a dark room. Suddenly, you see everything clearer. Whether you’re about to start dating someone new, contemplating the strength of your current relationship, bracing yourself for a breakup, or considering tying the knot, I’m here to help you navigate through the stormy seas of modern romance.

This guide isn’t about giving you all the answers—it’s about helping you ask the right questions to yourself, so you can make the choices that are right for you.


  1. Before starting to date someone
  2. Before getting into a relationship
  3. Figure out your relationship’s health
  4. Before breaking up
  5. After a breakup
  6. Before going back to the dating scene
  7. Questions to ask before marriage

Questions to ask yourself before starting to date someone specific

Before you go head-over-heels about someone who has come under the radar, let’s slow down and think this through. Assessing your feelings and expectations about this specific person can save you a heap of confusion (and heartache) down the line. Remember that it’s okay to take your time before committing. If your potential partner can’t deal with that, you might want to mark this as a red flag.

1. What attracts me to this specific person?

2. How well do I really know them?

3. What values and life goals do we share?

4. Have I seen them handle stress or conflict? How did they react?

5. Do they respect my boundaries and personal space?

6. How do I feel when I’m around them?

7. How do they treat the other people in their life?

8. Do they bring out the best in me?

9. Are there any red flags or deal-breakers that I’m overlooking?

10. Am I attracted to who they really are, or the idea of them I’ve built in my mind?

11. Can I see myself growing with this person?

12. How do they communicate their feelings and thoughts?

13. Am I willing to take on their past, complete with exes and baggage?

14. How do they handle their finances?

15. Are we compatible on a fundamental level, including our attitudes about important topics like religion, politics, or family?

16. Are they truly single and emotionally available for a relationship?

17. How do they handle disagreements or differing opinions?

18. Do they support my passions and respect my ambitions?

19. How do they act when things don’t go their way?

20. Do I feel I can trust them?

21. Do they show genuine interest in getting to know me better?

22. Can I be my true self around them?

23. Are they kind and compassionate not only to me but to others as well?

Before deciding, you might find it helpful to ask a few questions to get to know your new crush.

Questions to ask before getting into a relationship

Leveling up from dating to being in an official relationship is a big step. Before you slide headfirst into this, let’s take a timeout. This is the perfect opportunity for an internal reality check. Here are some questions to consider before you change that relationship status. Stay true to yourself and keep those eyes open wide.

1. Do I feel ready to commit to this person exclusively?

2. How well do our life goals and future plans align?

3. Do I trust this person completely?

4. Am I ready to deal with the conflicts and compromises that may come?

5. Do I feel comfortable expressing my thoughts, feelings, and fears to this person?

6. Does this person genuinely respect me and my boundaries?

7. Am I able to maintain my own identity and independence in this relationship?

8. How do I feel about introducing them to my family and friends?

9. Is this relationship enhancing my life and happiness, or is it causing stress and anxiety?

10. Are we on the same page about important things like finances, family, career, and values?

11. How does this person handle anger, disappointment, or other negative emotions?

12. Do they encourage my personal growth and self-improvement?

13. Is this person reliable, consistent, and dependable?

14. Are our levels of interest and affection for each other mutual?

15. Am I trying to change this person or hoping they will change in the future?

16. Do they appreciate and value the real me, without trying to mold me into someone else?

17. Does this relationship make me a better person?

18. Are we able to resolve disagreements in a healthy and respectful way?

19. Do they show genuine care for my well-being and happiness?

20. How do they treat the important people in their life?

21. Do they have any habits or traits that I can’t stand?

22. How do I feel about their past and their history?

23. Can I see myself with this person in the long term?

24. Is there equal effort from both sides in maintaining and nurturing the relationship?

When in doubt, don’t shy away from asking some deep questions to get into more details about your candidate.

Questions to figure out your relationship’s health

It’s all too easy to get so caught up in the lovey-dovey stuff that you overlook the fundamentals. A healthy relationship is like a well-oiled machine – everything should be running smoothly, with all parts working together in harmony. Here’s a list of questions to help you assess if your relationship is a healthy one.

1. Do I feel respected and valued in this relationship?

2. Can we communicate openly and honestly about anything and everything?

3. Are we able to resolve conflicts in a healthy, productive way?

4. Do I feel safe and comfortable expressing my thoughts, feelings, and opinions?

5. Is there a balance of power, or does one person tend to dominate?

6. Can I be my authentic self around my partner without fear of judgment or criticism?

7. Do we respect each other’s individuality and personal space?

8. Are our future goals and aspirations compatible?

9. Does my partner encourage and support my personal growth and ambitions?

10. Are we able to have fun and enjoy each other’s company?

11. Do we trust each other implicitly?

12. Do I feel happier and more fulfilled since being in this relationship?

13. Does my partner listen to me and take my feelings into consideration?

14. Are we mutually supportive during tough times?

15. Do we share common values and beliefs?

16. Is there mutual understanding, appreciation, and acceptance in our relationship?

17. Are we both fully committed and invested in our relationship?

18. Is there more joy and positivity than negativity in our relationship?

19. Can I express my needs and desires without feeling guilty or selfish?

20. Do I feel free to pursue my interests outside of our relationship?

21. Do we respect each other’s friends and family?

22. Does my partner behave responsibly and reliably?

23. Do I feel secure and loved in this relationship?

24. Are our disagreements and fights fair and constructive?

25. Can I picture a future with my partner?

Of course, no relationship is perfect, and there will always be bumps in the road. But it’s always a good idea to weigh the pros and cons to make sure you’re not trapped in a toxic relationship.

Questions to ask before breaking up

While breaking up an established relationship it’s a tough choice to make, sometimes it’s the necessary one. However, these decisions shouldn’t be taken lightly – like removing a band-aid, it’s sometimes best done after some careful consideration. So, sit tight and ask yourself these tough questions to ensure you’re making the right call.

1. Have I communicated my concerns or issues to my partner clearly?

2. Did we try to address and resolve our problems?

3. Am I considering breaking up out of anger or in response to a single event?

4. Do I feel happier, less stressed, or relieved when I imagine my life without them?

5. Have we lost respect for each other?

6. Are my emotional needs being met in this relationship?

7. Have I given the relationship enough time and effort to improve the situation?

8. Are our life goals and aspirations no longer aligned?

9. Do I still love my partner, or am I staying out of fear, guilt, or pity?

10. Am I consistently feeling unhappy, unfulfilled, or neglected?

11. Are we no longer able to communicate effectively or constructively?

12. Is this relationship negatively affecting other areas of my life, such as work or friendships?

13. Have I outgrown this relationship?

14. Am I staying in this relationship because of shared investments or financial reasons?

15. Are there recurring issues that we can’t seem to resolve?

16. Is there more stress, sadness, or frustration than happiness in the relationship?

17. Do I dread spending time with my partner?

18. Am I in this relationship out of habit, rather than genuine love or affection?

19. Have we lost our mutual trust?

20. Do I feel trapped or stuck in the relationship?

21. Have I considered seeking professional help, like a counselor or therapist?

22. Are there more negatives than positives when I think about our relationship?

23. Can I honestly see a future with my partner?

24. Is the thought of breaking up less scary than the thought of staying?

25. Do I deserve better?

You might like to read this article if you find yourself overloaded with self-doubt during your self-reflections process.

Questions to ask after a breakup

Breakups can knock the wind out of you, but they also open the door to fresh starts and new beginnings, sometimes in several areas of your life. If you’ve taken a blow, take some time to reflect on what might have sent things off course.

1. What can I learn from this relationship and breakup?

2. Did I lose myself in the relationship?

3. What were the deal-breakers or irreparable issues?

4. Am I holding onto any bitterness or resentment?

5. What positive qualities did my partner have that I want in my next relationship?

6. How can I use this experience to grow as an individual?

7. Was there a pattern in our issues that I’ve seen in my past relationships too?

8. What will I not tolerate in my next relationship?

9. How can I make my next relationship better?

10. Am I taking care of my mental and physical well-being post-breakup?

11. What part did I play in the downfall of our relationship?

12. Have I taken enough time to heal and process this breakup?

13. What were my expectations in the relationship, and were they realistic?

14. How have my feelings changed towards my ex over time?

15. What boundaries do I need to set in my next relationship?

16. Am I giving myself permission to grieve the end of the relationship?

17. What strengths did I bring to the relationship?

18. What were some red flags I ignored?

19. How do I feel about being single?

20. Am I ready to let go and move on?

21. What were the positive aspects of our relationship?

22. Did I communicate effectively in the relationship?

23. Am I clinging to hope of reconciliation, and why?

24. What do I want in my next relationship that was missing in the last one?

If you’re having a hard time recovering from the breakup or it’s taking too long to overcome it, you might want to consider therapy.

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Questions to ask yourself before going back to the dating scene

Do you really understand your own intentions, feelings, and readiness for diving into the waters of romance? Maybe you need some personal soul-searching first. This isn’t an exam – there are no right or wrong answers – just honest ones.

1. What am I truly seeking in a romantic relationship right now?

2. Am I genuinely ready to commit to another person emotionally?

3. How do I feel about my single status? Is it a choice, or am I feeling pressured to date?

4. What have I learned from my previous relationships?

5. What are my personal boundaries when it comes to dating and relationships?

6. Am I carrying any baggage or unresolved feelings from my past relationships that could affect my future ones?

7. What are my deal-breakers in a relationship?

8. What qualities am I looking for in a potential partner?

9. How will dating impact my personal goals and plans?

10. Am I ready to make compromises that dating might require?

11. Do I fully understand the difference between a healthy and unhealthy relationship?

12. Am I prepared to handle rejection if things don’t work out?

13. How much of my time am I willing to dedicate to dating and a potential relationship?

14. Am I ready to communicate openly about my feelings and expectations in a relationship?

15. Do I feel secure and confident in myself without needing validation from a romantic partner?

16. How would I handle conflicts or disagreements in a relationship?

17. Am I comfortable with the idea of being vulnerable with another person?

18. Am I willing to take the risk that comes with opening up my heart to someone else?

19. What are my views on intimacy and physical affection in dating?

20. How would I deal with jealousy or insecurity in a relationship?

21. How important is a romantic relationship in the context of my overall happiness and well-being?

22. Am I looking for a long-term relationship, or am I more interested in casual dating?

23. What is my stance on important relationship aspects like trust, loyalty, and mutual respect?

24. How will I ensure that I maintain my individuality and personal growth while dating?

You might find it beneficial to get some tips to fight loneliness after a breakup.

Questions to ask before marriage

Marriage isn’t just about the fluffy white dress, the five-tier cake, or the dreamy honeymoon. It’s about spending your life with someone, through thick and thin, in sickness and health. So, before you take the leap, let’s ask yourself some crucial questions.

1. Do I truly know and understand my partner?

2. Can I communicate openly and honestly with them about everything?

3. Are our future goals and aspirations aligned?

4. Do I trust them completely?

5. Are they not just my lover, but also my best friend?

6. Can we handle conflict in a healthy and constructive way?

7. Am I willing to compromise for our relationship?

8. Do we respect each other’s individuality and personal space?

9. Are our values, morals, and beliefs compatible?

10. Can we work together as a team through life’s challenges?

11. Are we emotionally, mentally, and physically compatible?

12. How do we handle finances and financial decisions?

13. Do I like the way they treat others?

14. Are they supportive of my ambitions and personal growth?

15. How well do we fit into each other’s families and social circles?

16. Can I imagine growing old with them?

17. Are they reliable, responsible, and dependable?

18. Do I feel loved, valued, and respected in the relationship?

19. Are we able to maintain a balance between our work, personal life, and relationships?

20. How do we manage disagreements and differences?

21. Can I see us raising children together, if that’s in our plans?

22. Are we able to discuss and negotiate our expectations and needs?

23. Can I be my authentic self around them without fear of judgment or criticism?

24. How has our relationship evolved over time, and am I happy with the trajectory?

25. Do I feel genuinely happy and content with the idea of spending the rest of my life with this person?

You don’t need to stop at asking questions only to yourself. You might also want explore some questions for couples to get to know each other with your partner.

Viktor is a Counselor specialized in interpersonal communication and relationships. He manages SocialSelf’s scientific review board. Follow on Twitter or read more.

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