My Divorce Advice Site Turns Five!

my divorce advice site

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

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, 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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    Divorced Girl Smiling welcome video
    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

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