Wondering If You Should Break Up With Your S.O? Ask Yourself These 5 Questions First

How do we know when and how to end a relationship?

How To Know When To Break Up With Your Boyfriend, Girlfriend, Or Someone You Love getty

Learning how to know when to break up with your boyfriend, girlfriend, or someone you love can be very difficult. 

Because, hey, breaking up is a big deal.

If you've been milling over the decision and asking yourself, "Should I break up with my boyfriend?" or "Should I break up with my girlfriend?"

There are a few things you can do. 

RELATED: This Is How You Know When It's Time To Leave A Relationship


Japanese organizing consultant turned Netflix star, Marie Kondo, offers sound advice to her clients who struggle with saying goodbye to things in their home they once loved. 

In her "Clearing out your closet" episode, she encourages people to take each item of clothing, hold it to their hearts, close their eyes and then see how it makes them feel.

Then she says, "If it brings you joy, keep it. If it doesn’t, thank it."

Saying goodbye to someone we love is never easy and it’s certainly much harder than saying goodbye to an item of clothing or "thing" we love or once loved. 

This advice doesn't just apply to cleaning out clutter.


If you're in a relationship and thinking to yourself, "Should I break up with my boyfriend or girlfriend?", this advice is just as useful.

How to know when to break up and how to go about it is just as challenging, if not hopelessly confusing at times. 

To make matters worse, we as human beings are wired for bonding, not for breaking up. 

Why is that?

Once upon a time, we lived in small tribes, had a small selection of potential partners to mate with, and often died around the age of forty.

And, if we didn’t, we then became the wise elders of our tribe who helped guide and advise the younger members and then died a few years after that.  

Our evolutionary biological "mating wiring" hasn’t caught up with the relationship dilemmas of modern love, one of which is, "should I stay or should I go?"


There are some people who are fortunate enough to find their life mates at a young age and successfully navigate that relationship through the many changes and challenges of life, in sickness and in health, until "death do they part".

Most people, however, will experience having two to three significant partners who "make sense" for different phases of their lives, during their brief, transitory, and mysterious trip around the sun. 

It means that breaking up with someone you love and ending a relationship — or having someone else end it — is pretty much inevitable, as is the pain that accompanies the ending.

Still, it begs the questions: how do you know if ending something is the right thing to do?


Shouldn’t you at least try to repair it before you end it? 

While the latter is generally a wise choice to make first, repairing and renewing doesn’t always happen. 

And if you are on the fence about repairing things before you make the decision to say goodbye or trade-in, you need to ask yourself a few questions first to help you make that decision.

So, when is it time to break up? Here are 5 things to consider if you're contemplating breaking up with your significant other.

RELATED: Should You Break Up? 7 Major Signs It's Time For You To Leave

1. Why did you choose them?

Think back to when you met this person. What part of you chose that person and what phase of life were you in?


What were you looking for and what did you want to experience? 

Sometimes, people choose a partner because they are looking to start a family. Sometimes, people fall in love.

Sometimes, people feel the pressure of social clocks and think that settling down is "the right thing to do".

Sometimes, people are lonely and looking for companionship.

Whatever the reason for your choice, know that there is no right or wrong reason for choosing someone, there’s just your reason.

2. What changed?

Reflect on the course of your relationship. When did things start to change? What role did you play in that change?

Remember: wherever you go, there you are. Your unconscious relational patterns will repeat if they are not tended to properly.


Answering this question for yourself is crucial for your well-being, regardless of what you choose.

3. Do you have regrets?

If you could "rewind the tape", so to speak, and change some things you did or said, what would those things be?

What do you imagine the outcome would have been if you could go back in time and get a redo?

Take some time to imagine this and get a felt sense of "what could have been…and… if only you had done…" and see what insights come.

Also, to help with any potential analysis paralysis with this line of questioning, see if your brilliant analytical brain can step back for a bit, while you explore your intuitive self.


4. What do you want now?

Does your current relationship feel like you are spending time with a synergistic soulmate and or pragmatic partner with whom you have a shared vision for the future? 

Do you both want the same things? Will possibly having different visions of the future work for you?

RELATED: If You're Feeling These 15 Things, You're In A Dead End Relationship


5. Does the relationship make you happy? 

Upon reflecting on the questions above, you may have found your answer to the question, "Should we break up?"

Now, it's time to follow Marie Kondo’s advice and honestly ask and answer whether or not your current relationship brings you joy.

If it does, then keep it, knowing there is no such thing as perfect.

If it doesn’t and you know that you have done your best, whatever that is to you, then thank that person.

Tell them how much they have meant to you, and how they’ve touched your heart.

Tell them how you’ve grown because of them, and how you know that you must do the next part of your life without them. 


Then, wish them well and say goodbye.

Consider giving them a small gift, perhaps a card or symbolic object, so they will have something of you to hold onto as the two of you transition into a new phase of life without each other.

And though you will feel sad while this chapter in your life’s story begins to end, in time, a new chapter in your life’s story will start its first outline, first sentence, and first paragraph.

And you, the author of your story, get to hold the pen to paper, while you create and then possibly start to co-create, a new story in your book of love and life.

RELATED: 5 Questions To Ask Yourself Before Breaking Up With A Toxic Boyfriend


Maura Matarese is a psychotherapist, author, teacher, speaker and workshop presenter, who aims to help people heal from heartbreak and navigate the stormy seas of complicated relationships. For a free chapter on divorce from her book, Finding Hope in the Crisis: A Therapist's Perspective on Love, Loss and Courage or Finding Hope After Heartbreak Workbook to help you heal your heart, visit her website.