Relationships are the sources of our greatest joys and our greatest hurts—sometimes simultaneously. And having robust, positive relationships in our lives is as essential to our health and well-being as nourishing food, clean water, and a safe place to live. In fact, the research is clear: Good, healthy relationships will add more than a decade to our life.

Here’s another truth: Even good relationships are messy and imperfect. They demand daily work and require productive conflict. 

Given these co-existing realities, how do you know when to leave a relationship with a friend, partner, spouse, or family member? When to end it with a business partner? When, regardless of relationship type, to say enough is enough, I’m done here? Then, once you’ve decided to do so, how do you exit without causing unnecessary harm? 

For me, a relationship social scientist, the how is the easier dimension. You leave with grace and respect. And pretty much the only pathway to executing a graceful, respectful ending is by doing the hard, internal work of honest reflection—a labor of important self-love done well before even approaching the exit ramp. 

To end a relationship with grace and respect is to do the emotional, internal work of embracing your humility (none of us is perfect) and of forgiveness (self and other). Both are essential ingredients if you are to find the courage to both articulate and own your needs and leave without emotional injury to the other. 

Will the latter always happen? No, not even for us who are theoretically well-practiced and highly educated in relational dynamics. I know because I’ve done it all wrong.

In my early thirties, my very best friend and I had the ugliest break-up, one even the most generous observer would describe as a dumpster fire of a fight and completely ungraceful ending: a conversation (screaming match) that picked up speed like seven-year-olds on an old school merry-go-round. The fight flung us both into an emotionally flooded realm from which neither of us could recover: the centrifugal force of our yelling, accusing, and defensiveness so powerful, accelerating out of control so swiftly, it ended with us abruptly (not respectfully, not gracefully) ending the call and the friendship. She yanked her landline cord out of the wall; I slammed the receiver of my office phone down so violently a colleague tip-toed over and asked if I was okay. It wasn’t my best moment, nor hers. The good news? More than a decade later we came back together in conversation to repair, apologize, and process that fateful day—and regrew our loving friendship, something I would never have predicted possible. Yet, as with most things in life, pain is our best teacher. We are wise to embrace her so that she can shape-shift us into better humans. 

Pretty much the only pathway to executing a graceful, respectful ending is by doing the hard, internal work of honest reflection—a labor of important self-love done well before even approaching the exit ramp. 

The when to leave is often the more complex, muddled dimension. It’s usually woven tightly around doubts and wondering. Have we (I) tried long enough, hard enough, well enough to make this work? Am I just too picky, prickly, petty? Perhaps things will change if I’m more patient? Less preoccupied? What if I work harder at being less forceful in my complaints and criticisms? 

Deciding when (if) to leave—when approached intentionally and mindfully—is typically wrapped in some fear, scarcity thinking, deficit model narratives, ambiguity, and what-ifs. What if she changes? What if he’s just going through a phase and it’ll get better once the kids are out of daycare, his mother is not ill, his business is more stable? What if I never find another partner or friend like him again? 

Let me be clear before we go further: Your safety is first priority. And no one else gets to make the assessment of how safe you are or aren’t in a relationship. You hold the truth of what your relationship looks like and feels like, and part of figuring out when and how to leave is figuring out how, for yourself, to honor your knowledge. If you’re in an abusive relationship, you likely already know that untangling yourself is not as simple as walking out the door. Those who have experienced domestic violence know something most of us don’t: Leaving the violent relationship significantly increases the odds they will be killed by their abuser. In her book Crazy Love (watch her captivating TED Talk here), domestic violence survivor and advocate Leslie Morgan Steiner explains why it’s very dangerous for someone to leave an abuser: “Because the final step in the domestic violence pattern is ‘kill her.’ Over 70% of domestic violence murders happen after the victim has ended the relationship—after she’s gotten out—because then the abuser has nothing left to lose.”

If you know someone who is in an abusive relationship, learn the above truths so you can be supportive, not harmful, as they navigate a safe exit. The how and when might literally be the difference between life or death. If you are currently in an abusive relationship yourself, contact the National Domestic Violence Hotline online or by calling 800-799-SAFE.

Where physical safety is not a concern, choosing when and how to leave a relationship is about confidently—sometimes boldly—choosing yourself (yes you can, yes you should!). Leaving a bad relationship is an important step toward reclaiming, and thus amplifying, your best self. 

How to leave

If leaving with grace and respect is the goal, how do you get there? How do you exit without regret, shame, blame? With forgiveness, generosity, and a courageous spirit of bravely creating your future?

In a phrase: You choose it. And then you mindfully plan it. 

To leave with grace and respect is almost always about not letting it just “happen” in the heat or wake of your next big argument. Rarely does a breakup you’re proud of happen without careful self-reflection, heart preparation, and even a bit of practicing what you’ll say, not say, do, and avoid doing. 

What does such preparation and practice look and sound like? Of course, it depends on the type and length of the relationship. Is this a friendship of a decade or a marriage of twenty-three years? A business colleague or your aunt, brother, or mother? Regardless, as is true with any high-stakes conversation, rehearsing what you’ll say with someone who knows you well and is willing to also challenge you is never a bad idea. Practicing increases the odds of going into an emotional conversation not only ready but able to own your own mistakes and foibles (we all have them) while simultaneously being clear, explicit, kind, respectful, and compassionate. 

Rarely does a breakup you’re proud of happen without careful self-reflection, heart preparation, and even a bit of practicing what you’ll say, not say, do, and avoid doing. 

Breaking up does not require, nor should it involve, breaking the other person’s ego or spirit. 

In fact, done well, leaving a relationship can be an opening for both of you. It should be an opportunity for you to build a multitude of things: confidence in yourself, future relationships that are better and more fulfilling, new tools for engaging in difficult conversations, and life’s next chapter—one you can begin after successfully wrapping this current relationship. 

Write it out

Writing out what you want to say, even if you’re not one to journal, is a helpful strategy when stress and emotions are involved. One simple approach you can try: Write 5-10 sentences, each finishing the phrase “I’ve realized that to be happy I need ______.” 

Review what you’ve written. Strike any hint or whiff of how the other person is to blame for your needs not being fulfilled. As tempting or true as they might be, it’s unhelpful to say them when leaving a relationship; they’ll just evoke defensiveness and cross-blaming. If you’re staying in a relationship, talking through core needs and how they can be fulfilled is a very worthwhile, necessary thing to do. But if your goal is to end it, blame and shame are counterproductive. 

Practice your talking points

Now look at your list again. Choose two or three of the sentences that best get at the very core of your needs and wants—those things that will move you toward your fullest potential and happiness. Practice saying those sentences out loud. You might even record yourself doing so, listening to them to get a sense of how they sound, how they might land on the other. Recruit a best friend or trusted colleague to role-play: You saying these things and them responding as the other might. 

Although it can seem robotic to literally write a script for ending your relationship, here’s what the research shows: “Overlearning”—practicing something so often it becomes second nature—reduces the chance we’ll default into fight or flight mode. When our adrenal systems take over, the odds of a respectful, graceful conversation are lower. 

Words matter. Choosing words that center your agency will inspire better and positive conversational energy and reduce the chance the other takes a belligerent or defensive stance. Being intentional about each word you use is the difference between your goal (respectful, graceful exit) and the antithesis (a dumpster fire, screaming match). 

As you practice your exit approach, focus on framing your needs and wants as yours and yours alone. Explain you’ve discovered and figured out these things while carefully reflecting on and coming to this decision. Others can’t really argue about our needs, preferences, and feelings when they are presented as ours and ours alone—as incomplete as they might be. 

The fact is, your needs are yours. You get to own them. And you should.

Avoid any statements that point to deficits in the other person or the relationship, such as: “You don’t listen anymore; we’ve never been able to communicate in this relationship.” Better is something like: “I’ve realized I have a hard time communicating what I need to you, and I want to try new ways of being in my life.” 

Avoid things like: “You’re never present. You’re distant and cold, always too focused on your own needs. We never talk about what we really need.” Instead, try: “I’ve discovered that for me to be happy I need to spend some time really working on myself, outside of a relationship. I’m excited to see how I can learn, grow, and become a better person.”

When we steer clear of pointing to the ways the other person isn’t able to fulfill our needs or has hurt us, disappointed us, or frustrated us, we keep the temperature of the conversation low while increasing odds of the respectful, graceful conclusion to both the conversation and the relationship.

Consider the conversation from an outsider’s perspective

Another helpful technique is picturing what the conversation would look like to a third party. What if someone was observing? If you had an audience, what would they feel about you after it was over: Horrified? Proud? Envious of your savvy skills? Angry about how you treated another human? Name you the villain, or the wise, competent interpersonal communicator?

Taking time to envision how you’d like the ending of your relationship to be felt will absolutely make it more like to actually play out that way. 

And while you can’t control how the other person will act and respond when you enter the exit conversation(s), you can and must prepare for your choices. Reverse engineering your graceful exit can make the process one that is more respectful and less dreadful for both of you.

Prepare for any scenario

What do you do if the other isn’t ready to reciprocate your respectful, graceful, and compassionate approach, wanting instead to escalate to anger and accelerate the merry-go-round of blame? 

Two things. 

First, honor the simple truth: Each of you has a perspective, and both can be valid. But, as with any and all viewpoints, each is incomplete. 

Think about it this way: You and another person go to a theatre performance on the same night sitting in seats right next to one another. Then after the show you’re each asked the same two questions: “How would you describe the main characters?” “What was your least favorite part?” Your descriptions and observations will be different even though you both saw the very same show!? Yes, both are true. And both are incomplete. 

A key to how to leave respectfully is to stay laser-focused on that simple fact: Their viewpoint is valid—and so is yours. They’re just different. And both are incomplete. 

A key to how to leave respectfully is to stay laser-focused on that simple fact: Their viewpoint is valid—and so is yours. They’re just different. And both are incomplete. 

Second, keep coming back to where you started: to owning your needs. Do so while simultaneously thanking the other for the many (good/great/awesome!) things the relationship has given you. Be generous in your gratitude for the warmth, love, friendship, adventures, and new perspectives. Make a list (for yourself) of the specific, best parts of your relationship so you have them top of mind and can say them out loud. 

Commit to generous doses of compassion. By definition, compassion is the “desire to alleviate another’s suffering when you perceive they are in pain.” Conjuring up compassion for another is actually not hard when we intentionally recognize their pain, their viewpoints—each of which is valid even as it is incomplete. Also remember that you’ve had more time to process this conversation and its outcome. For them, the adrenaline valve is likely wide-open, driving their (fight/flight) response. Yours is more moderated thanks to the preplanning and internal work. 

If desired, consider a final relationship ritual

If you’re ending a marriage or long-term partnership, you might want to co-create a final relationship ritual, one that mindfully pays homage to both what was (the relationship), what is (the transition, its ending), and what will be (new growth, next chapters). A divorce ceremony can be a positive, powerful opportunity to bless and release your relationship—one that can move you both more swiftly toward healing. It can be especially beautiful when children are involved, although equally as wonderful for two adults making the choice to create better lives, apart. 

Rituals by their very nature are designed to mark time, acknowledging the meaning and significance of that which is important to us. Intentionally marking the departure of our relationships through ritual recognizes the many contributions the relationship has made while, simultaneously, releasing us into its next form. 

What might rituals of goodbye or relationship-ending look like? 

• You could write each other a letter and agree to read aloud to each other before saying your final goodbye. 
• You might agree to meet at a place that was meaningful to you both and agree to each state three things the relationship has given you. 
• You each might bring an object symbolizing your favorite characteristic or trait of the other, placing the artifact in a symbolic place in nature (rock, waterfall, base of a tall tree, middle of a prairie), offering a blessing for all that you shared, and acknowledging that you each have many gifts to share with others. 

Rituals help the closure process. Keep in mind that closure for you (and them) might take a while—often longer than anticipated. Be patient, especially with yourself. Don’t expect even the most intentional rituals and goodbye conversations to be magical balms to your sadness, perhaps even anxiety, despite carefully choosing this path. 

Develop a mantra

I’ve found that in times of transition or uncertainty, developing a mantra is also helpful. In your journey toward releasing the relationship, a simple mantra said throughout the days ahead can be healing. For me, the simpler the better: “I consent to my happiness.” Or, “I choose myself.” 

Words are energy. They can serve as helpful reminders about why we’ve made the decision and why we’re sticking with it. 

Be clear about your future intentions

Finally, as you end your relationship, avoid leaving a crack in the door for future reconnection unless your intention is separating, not severing. A mindful separation can be a wise strategy for marriage, or when choosing estrangement from family members. If separation is your goal, it’s ideal that you and that person (or people) secure a licensed couples or family therapist, an expert who can walk with you as you work on your relationship or, perhaps, gracefully and respectfully split for good. In most other situations, offering even a glimmer toward a future relationship is disrespectful—giving a false hope on which to hang their heart. In these cases, avoid statements like “I’m just in a hard place in life right now, but maybe sometime in the future we will work.” 

Also avoid serving as their therapist, offering to provide ongoing support as they navigate and process the ending. You’re the last person they actually need as they find their new footing. 

One last thing, which should go without saying: Never end a relationship in text or email, unless you’re in physical danger. 

When to leave

In my mind and experience, when to leave is more complex because it comes with layers of questioning. Should I invest even more in trying to make this work? How much is too much adapting, bending, stretching? Am I trying to fix something that’s unfixable, and is it for the right reasons? Have I given this enough time? Enough energy? The proper type of investment? 

I asked a few twentysomethings about their perspectives on leaving relationships. My brilliant and witty twenty-one-year-old daughter happily weighed in, saying, “Leave when it sucks.” 

She’s not completely wrong. But some nuance is important. 

All relationships will suck at times. It’s part of the deal, especially relationships that are worth it. Harder to figure out is how much messy, angst, and conflict is too much? And which is of the healthy vs. unhealthy variety? What kinds of conflict and messiness are cancerous to the relationship? And which are actually okay and necessary?

All relationships will suck at times. It’s part of the deal, especially relationships that are worth it. Harder to figure out is how much messy, angst, and conflict is too much?

The best of best friendships and flourishing partnerships are going to suck at least some of the time. Essential is discerning the benign from malignant behaviors. In doing so, you’ll be able to determine the when (if) to leave—or perhaps realize you really might just need to work on healing and improving the relationship. 

To assess the level, intensity, and veracity of dis-ease in your relationship, I’d suggest a slightly different set of questions than those above. Honestly, humbly, and vulnerably working through the series of questions below will help you more clearly diagnose if the relationship you’re thinking about leaving should be in your past or part of your future. 

Grab a journal, a pen, a cup of tea. I suggest not working through all of these questions in one sitting. 

• What five words would you use to describe the quality of your relationship over time with this individual? Write them down. Study them. Let them soak in. (It can be hard to find the right words, so I’ve included a short list below that might help.) 
  • Generative, joyful, bountiful, neglectful, isolating, meandering, uncomfortable, flourishing, unsettling, nourishing, painful, heavy, light, passionate, playful, exciting, caring, gentle, loving, negative, tentative, rich, alive, dynamic, limiting, lovely, compliant, suspicious, hostile, dubious, hesitant, gratifying, generous, thrilling, captivating, pleasing, engaging, pleasurable, tiring, unpleasant, disagreeable, disappointing, satisfactory, decent, average, respectable, fine, amicable, gracious, warm, cheerful, priceless, enjoyable, ideal, superb, broken, incomplete, imperfect, positive, cheerful, joyous, jubilant, lively, bitter, miserable, adverse, colorless, cynical, peaceful, sparkling, light, heavy, abundant, plentiful, unusual, creative, stimulating, pessimistic, inspired, invalidating, antagonistic, oppositional, uninteresting, confident, ornery, unfortunate, disagreeable, enjoyable, gratifying, pleasing, cheerful, draining

• What five words do you wish were those you’d first use if someone asked you to describe the quality of your relationship? Compare your two lists. What are the differences? Why do you think those lists are not identical? Sit with these lists, letting them speak truth into your heart.

• When you’re with the person, do you often feel drained and unfulfilled? Or do you feel content, perhaps even energized? 

• Is this person generally open to your influence—willing to adapt, to follow your lead, to say “I love that idea!”? 

• After being with this person, do you feel generally better or worse about yourself?

• Does the “we” (your we-ness) prevail in your relationship, most of the time? Or is there a dominant sense of “me-ness” (my needs, my wants, my values, my opinions, my story, my goals)—one or the other of you having a “me” that takes precedent time and time again?

• Does the person blame you for their problems, suggesting that if only you would be different/act differently/think differently negative things wouldn’t happen as often to them?

• In this relationship, would you say there is a fairly equal give and take? Or do you feel like they do most of the taking and you do most of the giving?

• Do you tip-toe around expressing yourself, your needs, what makes you upset, or what you need to be happy?  

• Overall, would you describe this relationship as one characterized by feelings of contentment and security? Or would you describe it as a relationship characterized by often feeling unsettled?

• When you offer feedback or make requests that the other person stop or start doing something that is important to you, are they defensive? Or do they welcome your thoughts and insights with a sense of curiosity?

• To what degree do you feel like you need to change yourself to make the other person happy and less critical of you? 

• Does the relationship feel like it’s consistently an effort? Or does it usually give you a sense of ease? Of peace? Of feeling rather content?

• Overall, would you describe the relationship as generative—one that is helping both of you positively grow, adapt, and become? Or does the relationship often feel like you’re carrying a heavy backpack? If you could set that backpack down, how would you feel? Lighter? 

• What is one thing you’ve told no one about your relationship? Why do you think you might be hiding that thing from others? 

There’s no score nor right/wrong ways to answer the above questions just as there is no one answer about when and if you should leave a relationship. That said, once you get honest about the qualities and characteristics of your relationship over time, you can get honest about if it’s time to let it go or give it more work. 

And here’s the thing: If you haven’t had ______ (fill in the five words you chose that describe your ideal relationship, such as positive/exciting/generative/enriching/joyful), you might not know that those types of relationships are possible. Trust me, they are. Don’t settle. 

Yes, you might care deeply about the person. But, as one of my wise former students, Gen, recently reminded me, “Caring about someone is not the same as having a healthy relationship with them. Realizing the difference is where the processing of when to leave begins. And only you can do the work to understand when that is.” 

Still unsure? Ask a trusted friend what they think. Ask the hard questions, even the ones you maybe haven’t wanted to: “Is my spouse emotionally abusive? Am I seeing the relationship clearly? What might I be missing?” Then, be fully willing to listen to the answers, without defensiveness. It can be hard to hear that they think you’re in an emotionally abusive marriage or that your family or boss or sister is incredibly toxic. But do you want to keep on kidding yourself, believing all is well while most of the people you trust know it’s not? Most of the time, we’re not going to tell you until you ask. 

There’s just one last question to address: Why should you leave unfulfilling relationships?

Why to leave

This seems like a rhetorical question, right? We leave because we’re not happy, not thriving, lacking _______ (you know the drill; fill in the blank). 

Yet there is another reason. 

One of the most fascinating aspects of the research and teaching I get to do as a relationship social scientist falls at the intersection of our physical health and relational well-being. Thanks to decades of excellent research across many areas of study—from psychology to communication, from neuroscience to epidemiology, from psychiatry to cardiology and oncology and more—we now have data to clearly support what most of us humans intuitively know and believe: Good relationships are good for us and stressful, unhealthy relationships are shaving years off our lives. 

All relationships that need to end are—to some degree—toxic. They consume too much of your energy. They feel like a marathon of effort, most of it geared toward making sure the other person is happy. Is it time you focus on your joy and fulfillment? Perhaps it is.

Why leave a relationship that isn’t bringing you joy or helping you flourish? Because, as Dr. Robert Waldinger of Harvard reminds us: “Loneliness kills. It’s as powerful as smoking or alcoholism.” And, yes, we can be lonely even while in relationships, a truth many of us don’t want to admit. But we must. And then commit to the work of exiting (with grace and respect), which will eventually provide you with the freedom to find, create, and sustain the kind of relationships that are life-giving. 

All relationships that need to end are—to some degree—toxic. They consume too much of your energy. They feel like a marathon of effort, most of it geared toward making sure the other person is happy. Is it time you focus on your joy and fulfillment? Perhaps it is. And as you do, be graceful and respectful with the way you speak to yourself as you find that exit ramp. On the other side is, I guarantee you, freedom. 

And if you need any more nudging, consider this: Even the greatest relationship scientist, researcher, and therapist in the world, Dr. John Gottman, when asked what advice he’d give to his younger self, simply said: “Get out of bad relationships sooner.” 

I couldn’t agree more.