Coping With A Breakup Is Never Easy-Especially If It happens This Way!

By Jackie Pilossoph, Creator and Editor-in-chief, Divorced Girl Smiling site, podcast and app, Love Essentially columnist and author

coping with a breakup

Coping with a breakup can be extremely difficult and depressing, your heart feeling like it just got stomped on. But the end of a relationship can be even worse if the person who broke up with you does it in a way that’s less than considerate. Below is my Love Essentially column, published yesterday in Chicago Tribune Pioneer Press about a business that will break up with a person for you!


Online Business Does Relationship Ender’s Dirty Work  by Jackie Pilossoph

While technology can be amazingly helpful and enjoyable, I think the world is dealing with a double-edged sword when it comes to communication in dating and relationships.

Having just returned from a weeklong family vacation where I FaceTimed my boyfriend several times and thoroughly enjoyed seeing his cute face pop up on my iPhone, I find myself a huge fan of the technology. But, there is a downside to having so many communication options that take the place of face-to-face meetings. Technology has made it very easy to relay a difficult or uncomfortable message without actually having to say it to someone’s face. This includes a breakup.

I cringed when I recently heard about The Breakup Shop, a new online business that will break up with someone for you via text, email or a phone call.

Imagine this. You are sitting in your office hard at work, motivated by the fact that you have a great weekend planned with the guy you’ve been seeing recently.

You get a text, which reads something like:

Hi Stephanie,

We are sending you this message on behalf of Danny.

We regret to inform you that Danny is breaking up with you. Although you’ve had a good run and shared some memories along the way, it’s time to move on.

We offer you our deepest sympathies, and wish you all the best in the future.


The Breakup Shop

Here are my issues. How much colder and more insensitive can a person get than to hire a company to end a relationship? And, are people such wimps that they can’t actually find the guts or the consideration to personally break up with someone?



Feeling like I myself needed some therapy after reading the breakup messages available via The Breakup Shop, I reached out to David Klow, a Chicago-based marriage and family therapist, who said breakups are so difficult, they are often the catalyst that bring men and women into therapy.

“Breakups are one of the hardest experiences in life,” said Klow, a faculty member at the Family Institute at Northwestern University, who has been practicing for 10 years. “It’s the ending of an attachment or a bond, and sometimes that attachment can be more powerful than love. The disruption of something you are familiar with or comfortable with can be heartbreaking.”

In my opinion, hiring the The Breakup Shop is rubbing salt in the wound or twisting the knife. Thinking someone could be so coldhearted as to hire someone to send a text on their behalf, or worse, get some other guy or girl to call and do their dirty work, is beyond upsetting to me. It takes a selfish, wimpy and cruel person to hire The Breakup Shop.

But, since most people don’t aim to be selfish, wimpy and cruel, there has to be some appeal to The Breakup Shop, right? I asked Klow why he thought someone might use such a service.

“Many people don’t have the communication skills to face the challenge of a breakup discussion head on,” he said. “But if they learn how to communicate, and how to put their thoughts and feelings into words – which is often done in therapy, they are more likely to have an easier time. Communication takes practice.”


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Klow offered these tips to breaking up with someone in person:

• Watch the way you phrase things. Avoid using “I.” Instead of saying “I don’t think we are compatible” or “I need to move on,” try “We come from very different places” or “This doesn’t feel like a love connection.”

Be genuine and honest. Although difficult, most people end up appreciating a straightforward breakup. Men, in particular are sometimes conditioned to try not to cause pain, but they end up causing more pain and hurt by being indirect, vague and even dishonest.

I did find a redeeming feature of The Breakup Shop…Click here to read the rest of the column, published yesterday in Chicago Tribune Pioneer Press.

Read another piece I wrote on breakups!


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    Editor-in-chief: Jackie Pilossoph

    Divorced Girl Smiling is here to empower, connect and inspire you. Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling, the site, the podcast and the app. A former television journalist and newspaper features reporter, Pilossoph is also the author of four novels and the writer of her weekly relationship column, Love Essentially. Pilossoph holds a Masters degree in journalism and lives in Chicago with her two teenagers. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

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