Breaking Up Like A BOSS - When A Romance or Friendship is Over

I'm in love with the fantasy of ending relationships Like a BOSS. Not a mean lady boss, but the kind that remains awesome in the eyes of anyone with whom I've ever kept company.


In some alternate universe that reality exists. In it, I've stayed friends with all my ex's and maintained every friendship ever. My rotation of brunch companions is unlimited. Occasionally, we change it up and meet for drinks instead. No matter the setting we're catching up on the latest happenings and reminiscing about the good old days. Here, on planet earth, not so much.


The inspiration for my self-reflection, and subsequently this post, started innocently enough. I pinned a quote that resonated with me to one of my Pinterest boards. Apparently, it did the same for a lot of folks because my notifications went crazy with other people pinning it too. It was a simple statement yet very profound given the challenges I've experienced in relationships - romantic or not. The quote:

You are allowed to outgrow people.

When I recall the end of past romances and a few friendships, they've all been awkward (at best). Truth be told, some of my worst moments have centered around break-ups. Don't believe me? The following examples are real, and they highlight how NOT to end a relationship! 


By far, the most memorable was the one in which I found myself crouching down between two cars, to avoid an old boyfriend. It was the first time we had seen each other since our relationship ended, and I was hiding because we never "technically" broke-up. I offered no explanation or closure. He and I lived together, so yeah, you can imagine how awkward this was for both parties. One day I was there, and the next I was gone. It was an EPIC FAIL.

The guy before him, I just stopped calling. When he would call me, I would look at the phone while it rang, and rang. Knowing I should answer - one call or respond to his voicemail messages, but I never did. He'd come by the house, and I would pretend not to be home or have my mom send him away.  My M.O. in friendships wasn't any better.  I'd be less available for meetups or phone calls, beyond disinterested when I was present, and would ultimately fade out of the picture. I sucked.


So, if we're allowed to move on, why do we struggle so badly with ending relationships?  

You're probably not as bad at ending relationships as I was; at least I hope not. But if you are, don't worry, we all have to start somewhere, and if I can get better at it and move definitely can handle this like a true boss! 

Here are some tips that will help you improve your understanding of self and your approach to ending a relationship that has run its course. 



I believe the quote that started this strolled down memory lane says a lot about a common misconception we have about ourselves in relationships. Human beings often try to make a transient experience permanent. We take a good feeling and attempt to trap it in amber so it will last forever. We haven't permitted ourselves to release the people that no longer serve our best interests. It seems wrong and dismissive; like Donald Trump delivering his famous catch-phrase, "you're fired."  



I think I was just a REALLY slow learner for this lesson, and it kept coming back around, until finally (once and for all), I dealt with the underlying issues.  Chances are if you're reading this, you've been around the block a few times with this issue and are tired of reliving it. Take a look in the mirror and ask the tough questions. Do you distance yourself emotionally when a relationship has run its course? Maybe you aren't as nice to your beau or friend, hoping to push that person into cutting ties with you? Once you discover your patterns of behavior, it's easier to formulate a plan to overcome your obstacles.




From pattern recognition to making a plan. Write down what you want to say and rehearse it. Just like preparing for public speaking, stand in front of the mirror and talk it through.  As you become more at ease with your topic the less scary, it will be. It's true.


imagine if you were the one on the receiving end

Ask any guy, and they'll tell you the four most dreaded words in any relationship are "we need to talk." Every guy knows that's code for this relationship isn't working out, or you need to work on some things stat. I never wanted to be the person that potentially hurt someone else's feelings. I'd either hang in there too long or fade away, which in retrospect is far crueler. No one wants to be the person that someone stays with out of pity. It's better, for everyone, to make a clean break and start anew.



My very first best friend was named Tina. We lived in the same neighborhood and we were always together either at her house or mine. Her family moved, but before she left, we made plans to see each other. At first, we would have play dates, but it wasn’t the same. Our lives had changed, and the common bonds we had shared become irrelevant. The same thing happens when coworkers move on, our single friends get married or have kids. The ties that bound us so tightly together just aren't there anymore. The fact is some people are for life; others are for a season or several seasons, but not forever. It's okay to move on.



Along the way, you will encounter many people and a variety of situations. Some will be enjoyable, and others will be uncomfortable, but also necessary. Personal development, knowing what to do, when and how, is an evolutionary process. The clearer you become about yourself, and what you value, the more likely you are to make changes, even difficult ones. Friendships are just one area in which your evolution is reflected back. "As we gain a stronger sense of self, what used to matter no longer does, and we're bound to outgrow certain friendships," says Florence Falk, Ph.D., a New York City psychotherapist. "Once you're aware of that, without being cruel or feeling guilt-ridden, you can begin to let go of relationships that no longer nourish your most authentic self." To read more on ending friends click here a good feature in O Magazine


Being an adult ain't always easy, and stuff doesn't always turn out how you'd hope, so give yourself a break :)



The act of ending relationships revealed a deep-seeded desire to uphold my perception of self as the perfect partner or friend. I couldn't cope with the thought of someone disliking me or not living up to the ideal image that I had created for myself. Break-ups, romantic or otherwise, were in direct conflict with my relationship persona. Clearly, I still had some emotional growing to do.  


I can look back on the experiences as a bad breaker-upper (Seinfeldism) and see the error of my ways. I knew I had outgrown the folks in my life but had no clue, other than to disappear or fade away, how to wrap up the old and move forward. Having a conversation of that magnitude felt catastrophic. In retrospect, I might have been a tad dramatic. 


The humor is not lost on me either. I've come a long way from hiding between parked cars. I'm not quick to dismiss with a Bye Felicia, like Cookie. Not at all. But, I’m willing to have the conversation now. Something I was never willing to do before.


I bet you can too.


Always the best,