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Step-by-Step Guide on How to Heal from a Breakup and Date Again

"To open ourselves to the joy of a loving union means accepting the possibility of loss. To love, we need to accept the little losses of every day. We need to open ourselves to the inevitable daily losses of living, so we can open ourselves to love. Every breath connects us to life and then passes before a new breath fills us."

-Charlotte Kasl, If the Buddha Dated 

Let's face it. Breakups can be grueling. We can feel like the pain will never subside. Sometimes we may feel that person was the "one" for us. Other times, we know it wasn't right but feel the pain of the lost possibilities or fantasy of the relationship lodged like a smoldering ember burning a hole in our hearts. People often come to me in individual therapy or coaching and ask me, "how do you get over someone?" and while there is no quick answer to this, there is a deep grieving and letting go process I like to guide clients through in my relationship counseling in San Francisco. Today I will be sharing one of the most potent exercises we use with you. 

Things to Avoid after a Breakup

Before I begin this exercise with my clients, my client and I collaborate to ensure that the person grieving the relationship has created some psychological distance from their ex. We go over some things to avoid during the breakup and grieving process. This list usually entails:

  • Return all belongings; tie up any loose ends.
  • A no-contact period of at least 30 days 
  • No social media contact or internet stalking. Blocking or muting on social media can be helpful here to regain a sense of control over emotions and normalcy.

These things might not be possible in the case of a divorce, but we do our best to create boundaries and clear agreements that create a sense of safety and distance. 

At this point in the process, people usually ask me, "How long does it take to get over a breakup?" The answer to this question varies. Getting over a breakup can take a few months to a few years. I can say with certainty that the pain will decrease over time if you do the kind of deep work we discuss in this post. I can also confidently say that taking breaks from seeing your ex, stalking them on social or the internet, and generally creating distance (mentally, physically, and emotionally) from them will also ease the pain and stop stoking the fires of the wound. 

 When we end a relationship, we must grieve the wonderful and the not-so-wonderful things about it. Grieving is painful, but it also allows us to soften and open our hearts, which allows more love to come in in the future. When we grieve, it's important to honor and acknowledge equally the gifts and the challenges of the relationship so that we can learn and grow and not blindly repeat the same patterns in the next relationship. If we don't grieve and let go consciously and thoroughly, it's easy to find ourselves in a relationship that feels fraught with the same problems as the previous one. 


Often when we have a gripping fear of losing someone, it's tied to a string of unresolved losses from the past; to find our heart, we need to meet this reservoir of grief." 

-Charlotte Kasl 

The following exercise can help you reflect on and honor the qualities you may have attached to and those you may have resisted in your last relationship and help you find more profound harmony with these qualities. This exercise can help you feel whole as you carry the gifts of the relationship out into the world and soften the impact of the problematic aspects of the relationship on your hurting heart. 

Exercise: How Do You Get Over Someone? 

Grieve. So that you can be free to feel something else.

— Nayyirah Waheed, nejma

Day 1: What I Miss + What I Don't ("The Gifts" + "The Letting Go Pile")

1. Fold the paper in half. 

2. On the left side of the paper, write a list of all the qualities and things you liked about the person (their gifts and what you miss most about them). Include everything from internal traits or characteristics like their ability to let go, their warmth, and their sensuality, get as specific as you possibly can, the way they hold their coffee cup, and even try to capture intangible essential spiritual qualities like their style, their eyes, their financial status, their skills.

3. On the right side of the paper, write a list of all the specific qualities you don't like or would characterize as "needing improvement." Get specific here too. Write everything you didn't like, found challenging, or would like to release.

4. Look at the qualities on the left side, and group them into clusters of similar items. Title the cluster with a quality that describes that cluster. Qualities that don't fit in a cluster can remain on the list outside of the cluster. Do the same on the right side. You should now have a list of qualities/values vital to you on the left side of the page and a list of qualities that are either challenges, red flags, or deal breakers for you on the right side.

 Day 2: Integrating the gifts

5. When you have this simplified list, take a moment to go through each quality on the left side of the page and cultivate gratitude for the fact that you got to experience this firsthand in this relationship. Acknowledge how this present quality helped you grow, met your needs, and otherwise supported you and made you feel good.

6. Next, go through each quality on the left side of the page and ask if you embody this quality in yourself. Underline any qualities that you are lacking in yourself. From your underlined list, circle any of these qualities you could cultivate in yourself. 

7. Create a new list containing these qualities you can begin cultivating in yourself. Next to each item you list, write down a few ways you can cultivate this quality in yourself. 

 Day 3: Integrating the Letting Go Pile 

8. Go through the qualities on the right side of page one at a time. Take a moment to acknowledge how these qualities caused you or your partner suffering, and feel compassion for the suffering one or both of you experienced. Recognize that these moments of suffering may continue to teach you about your own needs and boundaries. 

9. For each of these qualities, ask yourself if there is a way in which you embody this quality that may have previously been invisible to you. Underline any negative qualities you recognize in yourself that you are willing to work on. Write the upbeat version of that quality next to it, i.e., next to "unreliability," write "reliability."

10. Look at the new list you created in Step 2. See if these positive qualities are already on that list. If so, see if you need to add other ways to cultivate these to your list. Add any new qualities you discovered in this step to that list, and write down a few ways for each you can build this quality in yourself. Relationships are mirrors, so there may be ways that the negative qualities of this person can reflect an area in your life that needs more attention and support!


Follow up: 

In addition to this exercise, spend time meditating on, contemplating, and cultivating these qualities daily. As you process the breakup, memories of the relationship will arise. Allow yourself to feel and honor them as you practice cultivating compassion for your suffering moments and cultivating gratitude for the good memories and takeaways of the relationship. A meditation that may be helpful as you allow yourself to feel your feelings and losses and process these memories is the Expansion meditation that you can find on my website. 

This exercise can be helpful when done alone or in the context of individual therapy or coaching. Remember, grieving breakups and losses takes time, so don't judge your timing! 



Someone can be madly in love with you and still not be ready. They can love you in a way you have never been loved and still not join you on the bridge. And whatever their reasons, you must leave. Because you never have to inspire anyone to meet you on the bridge. You never have to convince someone to do the work to be ready. There is more extraordinary love, more love you have never seen, out here in this vast and wild universe. And there is the love that will be ready.

— Nayyirah Waheed



Lauren is a Marriage and Family Therapist (LMFT 84371), author, dating coach, meditation teacher, and former matchmaker committed to creating relationship transformation through mindfulness, compassion, therapy, and social change.


Frequently asked questions 

Q.1 Why are breakups so hard?

A. We feel a deep sense of loss akin to a death when going through a breakup. We grieve all the good times in the relationship, and all the future possibilities we will never get to experience. Some people may feel this pain acutely and immediately. Others may have a delayed sense of grief as they go about their life, memories arise, or our partner isn't emotionally or physically available in moments of distress.

 Q.2 What does heartbreak feel like?

A. Most people have or will experience this at some point in their life. Many describe it as a heaviness, a dull or raw aching, a sharpness in the chest, yet others say it feels crushing. The pain may be acute and brief, or it may be chronic, lingering over days and weeks and draining your emotional and mental reserves like, for example, the pain from a back injury or a migraine. The part of our brain that registers physical pain is the same as the part that registers emotional pain. 

Q.3 How long does it take to get over a breakup usually?

A. The answer to this question varies. Getting over a breakup can take a few months to a few years.  Men have been found to have delayed reactions to grief, and may grieve silently or in isolation, throw themselves into work, or into a new relationship, thus often making it harder to identify when men are grieving. The pain will decrease over time if you do the kind of deep work we discuss in this post.

Q.4 What is the best thing to do in response to heartache or grief? 

A. Take the time to grieve it consciously and actively on a daily basis. First, name the grief. Identify what stage of grief you may be in and most importantly, let yourself feel your emotions - the good, the bad, and the ugly - with as much gratitude and acceptance as possible. For each stage of grief, there are different ways you can express and manage your emotions. 

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