10 Questions to Ask Before Ending Your Relationship

By Danielle Andrews

None of us knew how terribly these two fine people suffered in secret. I do not think that they ever stopped loving each other, but deep down in their nature, they did not belong to one another.

Hermann Hesse

Who we decide to be in a relationship with can be the most important decision of our lives. The person we spend most of our time with, the one we share a bed with, the one who mirrors back to us and forms how we see ourselves. Our intimate partners give shape to our lives and even affect how we interact with the rest of the world. So, if you find yourself in an unfulfilling relationship that seems to be draining you of your spirit, it’s time to take stock and decide if things can be salvaged or if it’s time to move on. Whether you’re just feeling out of sync with your partner or grappling with deeper conflicts, the decision to stay or leave can be overwhelming. Ending your relationship is a big deal, and it’s okay to feel uncertain.

Many people find themselves at this crossroad, asking themselves the same difficult questions. The good news is, there are ways to gain clarity. By asking yourself the right questions and reflecting on your feelings and situation, you can approach this decision with confidence and care.

Be Honest About How You Really Feel

1. Are you happy more often than not?

At its simplest, relationships should bring joy to your life. While every partnership has its rough patches, sustained unhappiness over weeks, months, or even years could indicate deeper issues. Ask yourself:

  • When was the last time you felt fulfilled in this relationship?
  • Do you feel that you laugh, connect, and support each other enough?

If the unhappy moments far outweigh the happy ones, it might be time to evaluate the root cause.

2. Do you feel emotionally supported?

Relationships are like home. They should feel safe, supportive, and welcoming. 

A strong relationship involves being there for one another in tough times. If you feel like your partner dismisses your emotions or fails to show empathy, ask yourself:

  • Do I feel seen and heard by my partner?
  • When I share my feelings, do they respond with care or defensiveness? 

Feeling emotionally unsupported can erode trust and connection over time.

3. Are your values and life goals aligned? 

We grow and change over time, and sometimes our paths may diverge from our partner’s. Consider the bigger picture:

  • Are your values compatible? (e.g., family, finances, career, or lifestyle)
  • Do you share a vision for your future together?

Differences in core values don’t always spell doom, but if they’ve become a source of unresolvable conflict, they can undermine the foundation of your relationship.

Questions to Evaluate the Dynamics of Your Relationship

4. Is the communication healthy? 

Communication is the heart of any relationship. If interactions with your partner consistently leave you feeling hurt or unheard, it’s worth taking a look:

  • Do we talk openly about our concerns and needs? 
  • Are disagreements handled respectfully, or do they escalate into blame, shouting, or stonewalling? 

Healthy communication is about teamwork, not winning arguments.

5. Do you feel respected as an individual? 

Mutual respect is an essential ingredient for any relationship. A lack of respect can manifest in subtle ways, like dismissive comments, or larger issues, like controlling behaviors. Ask:

  • Do I feel free to express myself without fear of being judged or belittled?
  • Does my partner appreciate my independence, opinions, and boundaries?

If respect is missing, consider whether the relationship can be corrected or if it’s time to walk away.

6. Are there recurring patterns you’ve tried to resolve? 

Some challenges are part of the growing pains within any relationship. Others, like recurring fights, dishonesty, or sweeping issues under the rug, can signal long-term incompatibility. Reflect on these:

  • Are the same problems resurfacing no matter how we try to fix them?
  • Have we truly given our best effort to address these issues?

If resolutions always feel temporary, you may be stuck in unproductive cycles.

Practical Considerations Before Making a Decision

7. Have you communicated your feelings to your partner? 

Before deciding to leave, ensure your partner truly understands how you feel. They can’t work on issues they don’t know about. Reflect on:

  • Have I been honest about my unhappiness and concerns? 
  • Have they been open to listening and willing to take steps to improve things? 

A meaningful heart-to-heart conversation often holds the key to clarity.

8. Have you sought help, like therapy or counseling? 

Sometimes, expert guidance is needed to untangle emotional knots. Professional counselors provide a neutral space to improve communication, manage misunderstandings, and find new ways to reconnect. Consider asking yourself:

  • Have we explored all options like couple’s therapy?
  • Am I willing to continue working on the relationship with outside help? 

If you’ve already gone down this road and nothing has improved, it may signal that the relationship’s challenges are deeper than what therapy can fix.

9. Are external pressures influencing your decision? 

Society, family, and fear of being alone can cloud your judgment. Some questions to reflect on:

  • Am I staying because of pressure from my family or cultural expectations? 
  • Am I afraid of what life would look like outside this relationship? 

It’s important to make choices that prioritize your well-being, not just those around you.

10. Who are you when you’re with your partner? 

Our relationships profoundly affect how we see ourselves. Think about:

  • Do I feel empowered, confident, and appreciated with my partner?
  • Or do I feel diminished, lost, or less like myself? 

The best relationships bring out the best versions of who we are. If this one doesn’t, consider if it’s still the right fit.

When the Answer Isn’t Clear

If these questions don’t lead you to an immediate answer, that’s okay. Leaving a relationship is not a decision to make in haste. Give yourself time to reflect. Journaling, talking with trusted friends, or consulting a therapist can all help bring clarity.

Take this “Relationship Satisfaction Test,” from Psychology Today.

Ultimately, the right path will become clearer as you tune into your inner needs and values.

A Final (Coffee-Date-Worthy) Thought

Walking away never means failure when it means you are choosing yourself. Whether you decide to stay and work on your relationship or move on and find new beginnings, know that you are worthy of love, respect, and happiness. Take the time you need and trust yourself to make the decision that feels right for YOU.

If you’re still looking for that special someone to share your life with don’t hesitate one more second! Our talented matchmakers here at Kelleher International are ready to help you navigate the process with one -on-one coaching while you get ready to meet your first customized match!