Dating 101: How to Handle a Break-up.

Photo Credit: Amy Lloyd

Read time: 10 min; SpeedRead: 1 min

It’s that time of year again… Hallmark cashes in and couples dish out. Romance is in the air and people are in love… except when they aren’t.

Some of you are in negative relationships, and some are still trying to pan out what happened months ago after a big break-up. Here’s something I wrote a little while back that should offer a few of you a bit of understanding and structure…


Your palms sweat and the tension rises. You know what’s coming. And then, in a flash, it is done. Your stomach feels like it just dropped through your ass. Confusion takes over as you search for a rewind button. “Why is this happening?

Breaking up is never easy, and it is never convenient. Most of the time you never see it coming, and it hits you when you least expect it. But it happens and somehow, we have to manage and figure out how to handle it.

There are two sides to every breakup. The person who got broken up with, and the person doing the breaking up.




It’s just not the same. Something is different. Maybe it’s them, and they aren’t the same person you fell in love with. Maybe it’s you, and you feel held down in a relationship with a future you can’t see optimistically. You go back and forth, not knowing if this is the right thing to do, if you’re making a mistake, if it’s just a mood, or if you’ll regret this decision for the rest of your life. But whatever it is, you are compelled to take action this time. You want to break up.


I want to break up, but I don’t want to hurt the other person. How should I do this?


First of all, it’s almost ALWAYS better to break up in person. Yes, it may be hard on both of you this way, but breaking up over the phone, or the internet ESPECIALLY, shows a disregard for your soon to be former partner’s needs. After you’re face to face, they will take it easier if you sandwich the breakup between two positives. Tell them how much you have enjoyed it up until now, tell them it’s not working out and why, and then tell them how great of a person they are. For instance:


This has been awesome so far. I’ve loved it. But I just feel like I need to be single right now. I don’t want to be held down, and I think we should just relax and explore our options. It’s not because of you, you are one of the coolest/ most amazing/sexiest/ greatest/ most adventurous/sweetest people I have ever met and any person would be lucky to have you.


After this, be prepared. They will have a lot of questions or might try to convince you to come back. To give them comfort in what is now a train wreck for them, try to answer all of their questions, openly and honestly (try to put a positive spin on your answers), and let them know you hope to be friends in the future.


Remember, just because you fell out of love with them and want to end it, doesn’t mean they have fallen out of love with you. Be conscientious of this fact. If you see they are dragging it out, and you are both talking in circles, YOU have to be the one to leave. They will not want you to, but staying longer than this will do more harm than good.




How are they doing?! Why haven’t they contacted me? Is he/she having more fun without me? I just hope they will be ok…


All of these thoughts will undoubtedly come into your head. So what do you want to do? Get answers! Find out, check in on them.


DANGER Will Robinson! DANGER!


You will have the overwhelming urge to contact them. You want to write them a message, give them a call. You want to be able to comfort them, in what you would hope is very hard time in their lives. But what you have to realize is- that is not your place anymore. They are not your boyfriend/girlfriend. You are not theirs. They need space; time to think about what THEY want, and time to heal. Constantly playing the role of comforter will confuse and ultimately irritate them. They are thinking “How could someone hurt me so bad, and cry about me hurting while trying to comfort me. THEY did this…” And trust me you will come up with excuses to find out how they are.


What if I just got in touch with their parents to thank them for everything and ask how they are; or maybe call their friends and ask if they’re ok, make sure they don’t hate me, but ask them not to tell?


This is all a very bad idea. You want to respect that the other person is hurting, and give them plenty of space. After a couple of weeks have passed, and it’s not a fresh wound, brief contact to ask them how they are or how they’ve been is polite and shows genuine care for the other person.


Aside: Dating someone else right away is also a VERY bad idea if you are concerned with your former love’s emotional wellbeing. See “Rebounding”


What if I feel like I made a mistake and want them back!?


Give them space after the initial break up. But if you feel like this, let it be known. Find a way to tell them why you have changed your mind, why you broke up with them in the first place, and why you want them back in your life. Honesty is the keyword here. However- just remember, they may not want to experience the pain you put them through ever again, and they may not want you back. Expect this and plan accordingly.



Everything was going PERFECT the last time you two hung out. The sky was the limit. You saw this relationship going nowhere but up. Then they give you the news. You will be confused, hurt, and unsure of a lot.


The first couple of days you may not even be able to eat, even if you’re hungry. Your autonomic nervous system is still revved up. Everything will remind you of them.


At first you won’t know what to do with your life. But this is secretly a good thing. It inspires action and motivates you to find something meaningful in your life and pursue it.


Your emotions for the first couple of weeks will come in WAVES- HUGE highs…then BOTTOMLESS lows.

One day you will be totally without a care in the world. The next you will be crying. This is normal. The more time passes, the more you will normalize yourself again and become a stable person as the waves don’t get so drastic in size one way or another.


You too, will want to contact your former other half. You want to know how they are doing, if they are seeing anyone, if they are really glad they hurt you. You will want to contact them and find any excuse to do so. You might also feel resentful and be angry at your opposite. Fight this.


You need space, you need distance- desperately. The faster you come to the understanding you can live without them in your life and you will be ok, the faster you will heal. Keep yourself busy with sports, clubs, friends. Go out, have fun, see a movie. The more you are around people, even if it’s just going to the bookstore, the better off you will be.


I TRIED keeping my distance! They keep contacting me!


Here is your dilemma. They are over you, and want to be friends as soon as possible. They want you to be in their life and comfort them like before, but don’t want to feel guilty for having fun and doing whatever they want. Basically- They are trying to have their cake and eat it too.


This is where you have to make a choice. Do you REALLY want to be friends? Or the better question- Do you REALLY want to be friends right now?


The answer is no. I don’t care who you are. The answer is no. You don’t REALLY want to be friends… you want them back in your life like they were, and you think if you hang out with them as a friend, they will like you again. HELL. NO. You will end up watching them date OTHER people, and you will be the ex they coming running to when they want to complain about how bad their new boyfriend/girlfriend treats them. DON’T be that person that becomes friends with a hidden agenda to get back together with them. It won’t happen, and you will end up hurting as they date other people and come back and tell you (their friend) about it.


I’m not saying don’t ever be friends, but be friends when you don’t have that feeling towards them anymore. Think to yourself, “If I saw them kissing another person, would I be upset, or unaffected?” If you would be upset, now is not the time to become friends. It may take a long time, but if you both respect each other still, you WILL be friends in years to come.


But I want them back!


You have to come to terms with the fact that you probably will never have them back. And do you REALLY want them back?


Because if you don’t or do, the answer is still the same- Space and Distance.


Relationships are different. They are paradoxical to anything else in our lives, and very counterintuitive. As human beings we are conditioned to believe that when something is falling away, we catch it or go after it. When something is slipping from our grasp we hold tighter to make sure it doesn’t fall. When our dog runs away, we run after it, we don’t just wait for it to come back home on its own accord. Relationships aren’t like this. If you want something back, it DOES have to come back on its own. You have to let go, and if someone doesn’t want to be in the situation they are in, squeezing them tighter will only make them push away more. As the old saying goes “If you love someone, you have to let them go.”

Give them the gift of missing you. You have to let them see what their life is like without you, and give them time to want you back in it. If you are constantly contacting and harassing them, how will they even have the chance to consider this? Luckily for us, whether we want them back, or don’t, the answer is still giving yourself some breathing room.


You may feel like you should get into another relationship immediately, hook up with any person you can. Bad idea. When you come into a new relationship RIGHT after you’ve left your old one, you are STILL going to care about your ex. This is called BAGGAGE. And like a terrorist with a bomb, this baggage will BLOW UP your new relationship. Guaranteed. Give yourself time to lick your wounds, heal, then come into a new relationship fresh, WITHOUT any hang-ups.


For a relationship to work it must have THREE essential elements.

  1. It MUST be the right time.
  2. You have to FIND the right person
  3. You also must BE the right person.


Let’s face it: we ALL think we are the right person for everyone and anyone. But the fact is, we are not. Just because someone is PERFECT for you doesn’t mean you are perfect for them; Visa versa.

But don’t forget time. You may be the right person for someone and they may be the right person for you. But if it’s not the right time in either of your lives, it still may not work.


All 3 of these are VERY important in having a stable relationship.


I’ve got to go hit the beach, but remember- You will have MANY people you love in your life. MOST of them you will NEVER marry, and you will end up breaking up with somehow. All you can do is learn and make the most of what you are given, enjoy the time you have, and move forward with your life.


You’ll be just fine.

Live, Laugh, Love



UPDATES: Working on a top secret post that contains tons of resources, and breaks down some BIG questions for Entrepreneurs. ‘Till then!

Posted on February 15th, 2012

5 People have left comments on this post

» Opey said: { Feb 15, 2012 - 09:02:09 }

Keen insight my friend. One point I’d like to add, if I may. After 15 years of marriage I can honestly say that people do not “fall” in love. We “Grow” in love. The Love I share with Angela today barely resembles the love we thought we had when we first got together. Patience, cooperation, openness, compromise, forgiveness and most of all honesty are things that take time to develop. Looking forward to your post for Entrepreneurs. – Opey

» Chase Doran said: { Feb 15, 2012 - 06:02:00 }

Thanks for the input, Opey. I agree with you 100%.

» Nomadic Samuel said: { May 15, 2012 - 01:05:26 }

These are all great tips. Relationships are never the same and breaking up with one person can be a totally different experience than with another depending on the significance of your bond and emotional attachment to the relationship. I’ve found though that time really does seem to heal all wounds and trying to be positive and proactive seems to speed this up.

» wessup said: { Sep 6, 2012 - 04:09:29 }

Thank you. This was helpful.

» Chase Doran said: { Sep 6, 2012 - 09:09:42 }

Thanks for you comment, and thank you for reading!

All the best,

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