My Divorce Advice Site Turns Five!

my divorce advice site

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

When I realized that the 5th year anniversary of Divorced Girl Smiling, (my divorce advice site) was approaching, I decided I wanted to do something really special, meaningful and important. So, I decided to throw a huge party, and make it a fundraiser for WINGS, an organization that offers shelter, support and education to victims of domestic violence.


The party planning wasn’t easy. It was another full time job to get sponsors for the event, find a good venue, explore different vendors, plan the details of the event, and then, the toughest part: selling tickets and making sure we filled the room to raise as much money as possible for WINGS.


My dear friend, Alisa, helped me so much. Together, we blasted this event out on social media constantly, we consistently sent personal emails and texts to friends, we asked people to help us promote it, and let me tell you, it wasn’t easy!! But in the end, the event ended up selling out, and we even had to turn people away because the room did not have the capacity to hold more than 175.

divorce advice
Me and Alisa!



If you didn’t come to the event, here is a sneak inside it, including pictures and a video of my speech.



The room was beautiful, the DJ was awesome (playing 70’s music), the food was yummy, the dessert table was amazing (thank you Stacey from Cookies by Design)-the one in the Glen Town Center,.


Vendors selling things were great!



and my sponsors, (who funded the event) were top-notch! They include:

Me and Elaine Moss of Vestor Capital


Katz & Stefani, Vestor Capital, Home Care Assistance, The Jerfita Team, North Shore Family Services, C.E.L. & Associates, Karen Covy, Discover Your Potential, Selective Search, Ruben & Goldberg, MAE Plastic Surgery and Transcend MedSpa, and the Collaborative Law Institute of Illinois.

Guests mingled, networked, laughed, ate, drank, shopped and learned about WINGS.






Me with Rebecca Darr, CEO of WINGS


My cutie pies!


I want to thank everyone who bought a ticket and helped this wonderful cause. I hope you had as much fun at the event as I did!


Lastly, thanks to the Divorced Girl Smiling sponsors, Katz & Stefani and Vestor Capital, who have made it possible for DGS to stay in business for 5 years. Also, thank you to my advertisers, The Center for Divorce Recovery, The Collaborative Law Institute of Illinois, MJ Gabel, and IIDV.


Why do I think Divorced Girl Smiling has been a success? Two reasons: one because of my readers, so thank you so much!! And two, because of my mission, which is to help men and women facing divorce know that they are not alone, that their feelings are validated, and that they can come to my site for support and information.


Remember, if you have the guts to look in the mirror and take some accountability for the divorce, if you focus on the future instead of the past, and if you always have an open heart, you have the tools for a better, happier life ahead.

Here’s to the next 5 years!

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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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