The Art of Heartbreak

A couple talking outside (Only view shoulders down)

Despite the good times, the memories, the wonderful things about this person that you’ve come to love, you’ve decided that it’s time to end it. You weren’t sure before but you’ve prayed and thought and discerned and consulted and now you know what you have to do. You just have to actually do it. Hopefully you didn’t come to this post hoping for an instruction manual (because there is none) but I hope that these reflections will provide you with some insight into one of the most difficult processes you will ever go through. Not all of these will apply to every relationship. You may also find some parts more or less relevant to you depending on who initiated the break up and how mutual it was. That’s why heartbreak is an art and not a science. While science approaches every question with a standard method, art has guidelines that are rarely if ever universal. In a similar vein, I advise you take what is helpful from this post and disregard what is not. If you are centered in prayer and consistently asking the Lord to purify your intentions from fear and selfishness, I think you will know which ones apply to you.

Without further ado . . .

 Before you do it

I’m assuming that you’ve long ago placed this decision in the Lord’s hands and discerned this break up long and hard in prayer. If you haven’t, stop here, go read part 1, and come back when you have a clarity of heart and mind in prayer. Once you have that clarity, I recommend praying what I call the “just in case I’m wrong prayer.” It goes something like this:

                “Lord, I think this is what you want me to do, so, in faith, I’m going to do it. If this is not what you want me to do, I need you to intervene in a big way. Derail this train.”

                After you’ve prayed that, proceed with the break up, barring any conspicuous STOP signs from God.

Next, prepare yourself for pain. There’s just no way around it. Breaking up sucks. It will not be happy. It will not be peaceful (although it can be amicable). However it happens, this is going to be unpleasant. Before you are done, you will break at least two hearts: your partner’s and your own. You, as the initiator of the break up, get an earlier start on processing and mourning the relationship but your heart will be broken nonetheless. You may not face the same feelings of rejection as your partner, but you will face feelings of guilt that they will not. Do not discredit your own pain because you were the “dumper.”

Your partner will be hurt. The person you love, the one you want to protect, the one for whom you would sacrifice to make happy: you are going to break their heart. You can try to minimize the damage. You can be as considerate and compassionate as possible, but it will still hurt. They will still be angry and upset. You will wound one of the most important people in your life in a way they will never forget. This is part of the cost of loving. We must be willing to be wounded and to know that as hard as we may try not to, we will wound. As St. John Paul II said, for love to be authentic, it must hurt. This is what the two of you signed up for when you fell in love (whether you knew it or not). This break up may be the place where you learn this lesson most palpably.

There may also be other people heartbroken because of your break up. Family members and friends may have come to love this person you have brought into their lives. Many may have derived great joy from your relationship. Some who have looked up to you and admired your relationship may be disappointed and disillusioned. Weddings, parties, and other social gatherings will be awkward when you show up alone and even more awkward when you are both there (and even more awkward when you both show up not knowing the other would.)

Also, a lot of you won’t want to hear this, but you and your ex will not still be friends when this is over. I’m sure somebody somewhere will tell that they are still friends with their ex after the break up but that is the rarest of rare exceptions. Maybe, if you were good friends for a while before you dated, or you were much younger when you dated and now some time has passed, or you didn’t date for very long and did not get very emotionally involved, being friends may be more possible . . . but probably not. You will probably never be close ever again until you meet in heaven.

None of this is to discourage you from going through with the break up, and it is certainly not license to cause more pain than is necessary, but you should prepare yourself for what to expect. Know that you can and should try to minimize their pain, but it still will likely be awful despite your best efforts.

Doing it

 What will I say?

                Plan out and pray about what is important to say and what is unnecessary. You may even want to list out talking points on your phone or a scrap of paper so that you don’t get lost in the emotions of the moment. Be as honest as you need to be. Don’t be dishonest, but you don’t need to include every injury and character flaw. Don’t be, as Taylor Swift says, “Casually cruel in the name of being honest.” Now is not the time to nitpick everything you don’t like about them. Yes, you should explain why you are breaking up with them. They deserve to know why and it will help them with their grieving process. It may even help them in future relationships to have received some honest, if difficult, feedback from you. In short, you probably will share some hurtful observations with them, but no need to add insult to injury.

Also, don’t say that you are “taking a break” or “just taking some time apart” or anything that implies that the relationship is anything less than over. Either you are with the person or you are not. Calling it a break may seem easier because there is less finality to it, but for that same reason will make the process more painful in the long run. Let them go. You have no right to keep them from moving on if you have decided that you are not going to be with them.

When and where?

                Think about your partner. At this point, you know them well and you know what upsets them and what brings them comfort. Will they want to be able to leave soon after the conversation? If so, don’t do it at their home where they will have nowhere to leave to. Will they want to hash things out for a while? Pick a place you can do that. Are they nostalgic about places and events? Then don’t break up with them at a place or event that might be tarnished by this painful memory. Don’t overthink this part too much because you can drive yourself crazy, but it does deserve some thought.

                Once you have said your piece and allowed them to respond, leave. You don’t need to hash it out all night. It’s normal and healthy to have a conversation but it doesn’t need to last hours. Also, beyond perhaps a goodbye kiss. I repeat: perhaps. a. kiss. That means, maybe (count it) one kiss and a hug, I definitely advise against any “one last time” gestures of affection. Emotions will be running high for both of you and it’s easy to do something you’ll both regret. I know a couple who had refrained from sex their entire relationship until the night they were breaking up when they decided to have sex because they had always thought their first time would be together and not with anyone else. Needless to say, it was a bad choice which they now regret and it complicated their breakup and later relationships.

                Except in extraordinary circumstances like a long distance relationship, the break up should happen in person, face to face, out loud. Not over the phone or video chat. Not in a letter or email or text. Yes, it’s more difficult, but it’s the right thing to do. One possible exception to this is if you have tried to have the conversation several times and your partner keeps shutting you down or becomes belligerent. In that case, a letter, in which you explain that you have tried to do this face to face, may be appropriate.

What if I didn’t know this was coming?

                First of all, I’m so sorry this has happened to you. The person you love has decided (and perhaps discerned) something that you have not. I’m sorry that you don’t get a choice. I’m sorry that you didn’t get time to prepare. All I can say (from the experience of having been in your shoes, abandoned by someone I thought I would grow old with) is that you will be ok. You are not unlovable, you just aren’t meant to be with this person. Someday this will all make sense. I know that all sounds cliché (because it is) but it’s also true. You will get through this. Take courage and trust in the God who loves you. This is only one chapter in your story.

When it’s Done

 It doesn’t matter who dumped who

For some reason, this is the first thing we want to know when we hear that two friends have split but really it’s meaningless. The relationship ended. Forget about who dumped who. Take no special pride for having ended it, take no special pity for not. Nobody won or lost. It’s just over. You are both broken hearted. It doesn’t matter who pulled the plug on a failing machine.


                Be sad. Be angry. Let yourself grieve. Don’t be destructive (to yourself or anyone else), but let yourself feel those emotions. Don’t sweep them under the rug. Listen to Usher, Maroon 5, Paramore, Linkin Park, and Taylor Swift. Cry. It’s all part of the process. That said, try not to dwell on the pain too much either. If you are finding yourself spending hours at a time detached from the world, you may need to find a healthy outlet to take your mind off of it: friends, exercise, travel, etc.

You may also find it helpful to talk to a counselor or therapist. No, it does not mean that you are crazy, just that you are human. Stuff like this is what they are for. Especially if you’ve never tried counseling before, you may find that a few sessions do wonders for you. Don’t knock it ‘til you’ve tried it.


                Anytime our human relationships fail us, it is a good time to turn to the unfailing love of God. Take some time each day to connect with the Lord. Read the scriptures (especially the psalms,) go to mass, confession, and adoration. When you feel hopeless and overwhelmed, lay your heart at the foot of the cross. One of my favorite prayers is to write down a list of everything on my heart and then one by one, offer each item to Jesus. Even in your anger and despair, cast yourself on him. He can take it. Go to him. Rely on him. Love him.

But you don’t need to pray for your ex all the time

This may seem counterintuitive but not praying for my ex was some of the best advice I’ve ever received. After a nasty break up, I was consumed with praying for my ex to the point where my spiritual director advised me to stop praying for her. He said something to this effect:

Yes, it is good to pray for people, especially people you love who’ve hurt you. But you know who loves her more than you? God does. He is watching over her. He does not need your prayers to love her, especially if praying for her comes at the price of your emotional well-being. Entrust her to God’s hands and let go. Praying for her is not really your job anymore.

People in relationships care for many of each other’s needs. After a break up, it’s natural and right to step back from that role. You no longer call just to check in, make dinner together, or run errands for each other. Neither should you pray for them at the same level as you did when you were together.

Be active, but not too active

                 You will have more time on your hands. Invest your time wisely. Reconnect with activities, and friends that you may have let slide. Do things you enjoy. However, be careful that you are not just keeping yourself busy so that you don’t have to feel the pain. There’s a delicate balance to maintain here.

Don’t get back together

                Especially, do not meet up just to talk. Do not meet up just to make out or hook up. This is like trying to cure a hangover with more liquor. You will temporarily relieve your immediate pain but greatly increase your overall, long range pain. Trust me, it will only make things worse. This is almost always a bad idea unless something significant has changed (like long distance became short distance). By the way, “I didn’t realize how much I really loved you” is a bad reason to get back together. You will naturally feel a surge of longing for the person you love after you break up. It doesn’t mean you should get back together. This will be especially tempting for you if you were the dumped and the dumper decides they want you back. Don’t fall for it.

Give each other space

Give yourself and your ex some distance. You both need time and space to heal. It doesn’t mean you have to avoid each other at all costs, especially if you are part of the same group of friends, but you may want to avoid running into each other for a few weeks at least. Especially if you initiated the break up, I advise you to give them some space for a little while. It may mean missing the next party or attending a different mass for a few weeks. Once you’ve given some time for the sting to dull, you can stop worrying about it. If you run into each other, so be it. The two of you will figure out the new normal in time.

Don’t throw Hexes on Your Exes

                Don’t talk bad about your ex. You probably need to vent and process with a few close friends but you do not need to tell the gory details of the relationship and break up to everyone. If you find yourself confiding in more than just a few people regarding the pain the other person has caused you, then you are probably casting the circle wider than it needs to be.

Even in your own mind, try not to villainize the person or your relationship. Try to prayerfully make an honest reckoning of the situation. The fact that the relationship ended doesn’t mean that you weren’t meant to be together, just that you weren’t meant to be together forever. The good of your relationship was still good. Your ex still has many good and beautiful things about them and you were/are right to recognize and be attracted to those good and beautiful things. The time you spent together was not wasted. You learned much good from each other. That doesn’t go away just because the relationship ended.


                Spiritually, forgiveness is an act of the will that you choose. Psychologically, it is a state achieved in one’s heart. You cannot make yourself feel forgiveness. However, if you choose with your mind and will, to forgive, it will start you on the road to forgiveness in your heart. I was once told that forgiveness in your heart happens 2% at a time. That means you may have to willfully choose to forgive someone at least 50 times before you start to feel it in your heart. After a painful break up, I struggled to forgive this girl who had hurt me deeply. In prayer, I told God many times that I forgave her and asked Him for the grace to feel it. One day, an image came to my mind that my heart was a chunk of ice that I would bring out into the sun each time I prayed. Every time, it would melt a little bit. Eventually, when I told God that I forgave her, I felt it.   

                You will too. In time, healing will come. Trust in the Lord who makes all things new (Rev 21:5) and gives us new hearts (Ez 36:26). You will hurt for a while. And then you will hurt less. And then you won’t hurt. If you are going through a break up I am so sorry, I feel you burning, and I am praying for you.



What are your thoughts? What have I missed? Share your wisdom and your stories? What have you learned from break ups? What do you know now that you wish you had known then?


Written by the Holy Rukus