how to gently break up with someone

How To End A Relationship
With Love And Compassion

Today’s article on navigating breakups comes from my close friend Jason Connell. Jason is a psychotherapist and meditation teacher in training. He is also a world-class consultant in leadership and professional speaking. He’s always thoughtful and he’s the perfect person to tackle this sensitive subject.

Earlier this year: I’ve failed. In my hand is a note that reads, “My intention is to be my best self. To be loving and gentle until the last moment.”

Like an asshole, I did the opposite. I came in guns blazing and left cold, angry, and closed. We both knew the relationship was over; there was no need for hostility.

I muster whatever energy I can and text her, “Hey. I kinda messed that up. I assume you’ll say no to this, but is there any chance I can come back over? There were so many things about you and us that really made an amazing difference in my life and I wanted to share those too before we fully said goodbye. Certainly do what’s best for you, but if it’s at all possible, I’d love to end on a better note, one that’s more reflective of what you were to me.”

To my delight, A* texted back saying she felt the same way. We spent an hour on her balcony, holding hands, drinking wine, watching the sun set over the Rockies, and reminiscing about the good parts.

We kissed, referenced a joke from the beginning, and said goodbye.


Breaking up with someone you love is one of the hardest things you’ll ever do. A part of you dies as two souls untangle themselves. Because of that, making the decision to break up with someone is also exceptionally difficult.

In this article we’ll discuss the messy process of breaking up with someone you love. More importantly, we’ll talk about how to do it with care and grace, both for yourself and your ex. We’ll also discuss different approaches to healing after a breakup, allowing you to be better off in the long run.

Is it really over? How to figure out if you should end your relationship.

Is it really over

Almost everyone struggles to figure out whether they should stay in a rocky relationship or end it. This is especially difficult if you’ve been with your partner for a while. Here are some questions to help you figure out what’s right for you.

  • In your heart of hearts, do you know that you and your partner are wrong for each other? If so, it’s likely time to end the relationship.
  • Do you feel safe physically and emotionally? If not, please end the relationship as soon as you can.
  • Have you talked to your partner about what’s not working for you in the relationship? If not, now is a good time to do so. Sometimes we harbor grudges and concerns that feel so insurmountable, we don’t bother bringing them up. While I understand the reluctance, giving into this is a bad idea. It’s much better to talk to your partner about the stuff on your mind. Perhaps the two of you will be able to solve the problem and improve your life. If you remain stuck you will have gained important clarity about incompatibility, which will make ending things easier for both of you.
  • Have you talked it over with a close friend? If not, now’s the time to do it. Text or call your friend and say, “Hey, I’m really struggling with a decision. Any chance I can talk it through with you?” Encourage your friend to speak candidly. He or she may be able to offer insight. A few years back I had three close guy friends say, “Dude, you need to break up with that woman” and then explained why. Though it was hard to hear, their advice made my life better.
  • Are you just staying in the relationship because you’re afraid of being alone, afraid of starting over, or afraid of hurting the other person? While I certainly understand the fear, that’s a shitty reason to stay with someone. Not only are you making your life worse, you’re making the other person’s life worse, too. It’s time to break up.
  • Are you afraid that if you break up either you or your partner will never bounce back? Again, I’ve been there. The good news is that this is almost always a false fear. Both of you will be fine. Humans are resilient. I promise. In many cases, people heal more quickly than they expect. Earlier this month, a recently divorced friend said that her divorce made her realize something: her ex-husband spent years making her feel small. She’s been delighted to find out that without him, she’s more capable and powerful than ever before.

Don’t answer these questions quickly. Instead, take your time to mull them over, journal, and reflect. The decision to end a relationship is significant. While it’s not always possible to be 100% sure that you’re making the right decision, you do want to be sure enough before you pull the trigger.

How to break up with as much grace as possible

Break up with grace

If you’re the one doing the breaking up, it’s important to realize that things may go poorly. Your partner may be hurt, they may say cruel things, or they may beg for another chance. If this happens, realize that it’s a natural response to the vulnerability of rejection. To the best of your ability, remind yourself that she doesn’t mean what she’s saying.

Of course, it doesn’t have to be bad. There are things you can do to set the stage for a loving and gentle breakup.

  • Call on your best self during the breakup. Endings matter. Almost all of us become ghosts of our best selves when dealing with heartache. When thinking about how you want to break up with your partner, ask, “If I were the best version of myself, how would I handle this? What would I say? What would I do?” That’s why I had a note in my pocket. I wasn’t naturally going to be my best self, but I still wanted to give A* the best I could offer. While you may not get it exactly right – I didn’t – the mere act of intending to do your best should help.
  • Give your partner a heads up. A few hours before you get together, shoot her a text saying, “Hey, wanted to give you a heads up, there’s some tough stuff we need to talk about tonight. Does 7pm at your place work for you?” Doing so will give her a chance to brace herself and preemptively reach out to her support system.
  • Break up in person (with a few exceptions). If you’ve only gone on a few dates it’s probably okay to break up with that person by text or phone, especially if you haven’t slept together. But if you’ve been together for a while, end it in person. She deserves that. You deserve that. One important exception: if you fear for your physical or emotional safety, don’t break up in person. Instead, use whatever medium feels safest and make sure friends are around.
  • Pick the venue with thought. No matter how disorienting it is to dump someone, it’s going to be even worse for the person who just got dumped. Though it’s a matter of controversy, I think the best move is to break up at the other person’s home. This way she doesn’t have to go out in public right after being broken up with, she can send you away if she’d like to, and she’s already in a space where she feels safe and comfortable.If you live together, consider making plans to stay at a friend’s place for a few nights. In almost all cases, I’d err against breaking up with someone in public. The exception to this, is if you believe that you’ll be physically or emotionally unsafe. Your safety matters more than anything.
  • Say what you need to say, but not more. Focus the conversation on one or two definitive reasons about why you should breakup. This is often easier and kinder than listing the million reasons you’re wrong for each other.Make sure that it’s clear that you’re breaking up with the other person without being needlessly cruel or verbose. Something along the lines of, “Look, I don’t think this is working and we need to break up. I adore you, but I don’t adore us. This isn’t right for me and I don’t think it will be in the future. Specifically _________________ isn’t working.” It’s worth practicing what you’re going to say a few times. If you have friends who communicate well, ask them to spot check your approach.
  • After you’ve broken up, listen. Let her react. Answer any questions she may have. If you can, avoid falling into the trap of berating one another. If your ex starts berating you, set a boundary and try to change the tone by saying, “Look, I get it. I’m upset too. You meant the world to me and I’m crushed that we couldn’t make it work. If you’re just going to abuse me though, I’m going to leave. This is hard for me, too.” If she keeps harassing you, just leave. If she asks you to leave, leave.However, if you notice that the breakup seems to be mutual and you and your ex still seem to care about one another, you might share a few of your favorite parts of the relationship. Let your ex know just how much they meant to you. This requires skill and luck, but if the two of you can pull it off, it’s really beautiful and healing.
  • Finally, set boundaries. If you and your ex have been together for a while, the logistics of breaking up will require thought. You’ll need to return your things, get separate apartments, and untangle any shared projects. You may also want to ask questions or share thoughts in an attempt to move closer to closure.This will all be made easierr with clear boundaries. I’d suggest agreeing on some finite amount of time (two weeks or so) before going no contact for a while. (By the way, it’s not 100% clear to me that closure is even fully possible.) More on closure and letting go from Nick here.

Looking for a few more ideas on how to break up with someone and how to tell if it’s really time? Check out, “How To Breakup Without the Heartache.”

Taking care of your ex after your breakup

It’s normal to want to check in with your ex. To say hi, to make sure she’s doing alright, to reminisce, and to cut through the loneliness you’re feeling. You may also feel a strong urge to make sure that she’s okay and see if there’s anything you can do for her.

Unfortunately, you’ll have to let go of those urges. She’s a capable woman. She has friends and family to lean on. She’ll be alright without you.

If you want to help her heal: respectfully breakup with her, honor any boundaries she’s set, and work to heal and improve your life….

Taking care of yourself after a breakup


So much energy goes into the breakup itself that we often forget to take care of ourselves. Instead of working to heal the pain and improve our lives, we get hung up on the loss itself.

While I think it’s important to mourn, grieve, cry, and scream, it’s also important to make this process as easy as possible. I’ve made a list of strategies to help care for and return to yourself post-breakup. Experiment with a few of the ideas below. If one or two excite you, invest in them. If one or two freak you out, become curious about why they’re unappealing. Answering that question has the potential to shed light on blind spots in your life.

  • Make a list of everything you disliked about your ex and your relationship. Keep that list on your phone. Seriously. Everything. How dry her hair was, how small she made you feel, her ambivalent attitude about sex and intimacy, her immaturity, her taste in music, her horrible communication skills, her coffee breath, whatever.Often during a breakup your mind will play a cruel trick on you: it will exaggerate the good parts of your partner while ignoring her bad parts. Don’t fall for the illusion. Instead, train your attention on the reasons she wasn’t right for you. When you notice yourself pining for her, reread that list on your phone. When you think of other stuff that you’re excited to no longer deal with, add it to the list!Hat tip to Guy Winch’s excellent book and Ted talk on breakups.
  • Temporarily lower the bar in life. You’ll be wobbly for a little while after the breakup. For now, set the bar for life lower than normal. Do the minimum at work, skip the social functions you’re dreading, eat a bunch of chocolate bars, sleep in, and spend some money on yourself. Doing this will allow you to rest and recover. It will protect you from the world when you’re feeling particularly vulnerable. You can pick up the slack next week. For now, it’s okay to be hurt.
  • Schedule some cool stuff for yourself. Get a cigar, a mango donut, or a decent bottle of scotch. Take a trip, fight for a cause, start hitting the gym, learn the ukulele, or buy Lumineers tickets. In almost all cases, breakups temporarily create a deficit of joy and social contact. Start filling the void with treats for yourself and projects that will make you a better person.
  • Dedicate meaningful time to reflection. Personally, I bought a journal dedicated to the breakup. Each morning I spent 15 minutes or so writing about whatever was on my mind without judging it. Another approach is to ask yourself bold questions in your journal (g., “what’s the most important thing I can do today to help myself heal?”) and then start writing without thinking about it too much. You might be surprised by the wisdom resting within. You don’t have to journal daily, even once a week will help.Bonus points: if you really want to dig deep and heal, consider enlisting the help of a good mental health professional. Breakups suck. A good therapist can help alleviate the pain while helping you become a better version of yourself. In some ways, you’d be nuts not to work with one (though I’m extremely biased). Here’s how to find a good one.
  • This is probably the most important advice I can give you: lean on your friends and family. Write them emails and texts talking about how you’re doing. Invite yourself over for dinner. See if they’re available to grab a drink. Call to tell them what’s on your mind. One of the hardest parts of a breakup is that you’re losing the main person you were sharing your life with. Feeling lonelier than normal is inevitable. Fill some of that space with your friends and let them take care of you for a bit while you get back on your feet. Bonus points: if you know you’re going to break up with your partner, let your friends know ahead of time. Ask them to meet up with you or take your call after the breakup. Knowing that you have someone standing by who cares about you will make all of this easier.
  • Avoid the tendency to rush into the next relationship. I know that it’s tempting to run into the arms (or legs) of the next person who will have you, but that’s a bad idea and you know it. Doing so will only prolong the pain. You changed a lot during your relationship and it’s important to get to know yourself Once you’re (mostly) loving life again, then you’ll be ready to start dating, but not before.
  • Don’t contact your ex. Or hang out where she hangs out. Or go on her social media. Or come up with some BS excuse to go over to her place. I know it’s hard, but this is the time you need for yourself. Did you make that list of all the things you disliked about your ex? Each time you’re thinking of reaching out to her, read that list instead.

Looking for even more tips on how to get over an ex? Check out Nick’s excellent article, “15 Best Ways to Get Over a Breakup.”

If you’re reading this, then there’s a good chance that you’re considering breaking up with your significant other, or already have.

A very real part of me is sorry for you. That pain, confusion, and loss that comes along with a breakup can be totally dominating. Especially in the beginning. I hate that you have to deal with that. As you know, I’ve been there.

But if I’m being completely honest, a part of me is excited for you. Your relationship wasn’t meant to last forever; if it were, it would have. Take some time to read the lessons, work to get back on your feet, and once you are, work to become an even better version of yourself. Doing so will make a dramatic difference in your life. It will also make you even more attractive than you already are.

Hey, Nick here again. Hope you enjoyed Jason’s article and that it’s helped you during a time of need. If you haven’t already checked it out, Jason has an amazing body of work on emotional intelligence, people skills, and inner work. You can read his work here