Jackie Pilossoph

We understand what you are going through.

Divorce is hard. It’s upsetting and stressful and scary. We’re glad you’re here because Divorced Girl Smiling is the place that connects people facing divorce with trusted, vetted divorce professionals, with the goal of giving you the best divorce outcome and a great post-divorce life. Divorced Girl Smiling (DGS) is a community, and a place you can visit to get educated, empowered, and just feel better before, during and after divorce. We’re here to validate you, inspire you, and help you feel supported, confident and loved.

I’m a former Chicago Tribune columnist and TV news reporter who went through a divorce at age 41 with two toddlers. It was a lonely, isolating time. That’s why I took my pain and turned it into a company to help you. It’s my personal mission to help people facing divorce feel less alone, get through the process more smoothly, and live life happily and with health after divorce.

Stop worrying and start smiling! We’ve got you!

Sincerely,

Jackie Pilossoph

Founder
Divorced Girl Smiling

Divorced Girl Smiling

Wonderful guidance!

“I love the guests she has on and the topics are so relevant and helpful.”

A can’t miss!

“Jackie provides support, thoughtfulness, and levity to those going through the tough time of divorce. She is the best girlfriend every person going through divorce deserves!”

Makes a difficult process so much easier!

“She’s been through it and she knows how hard it can be, especially with young kids.”

Divorced Girl Smiling Podcast

Grab a cup of coffee or a glass of wine and join us! You’ll be smiling in no time!

Every episode is hosted by Jackie Pilossoph, along with one of the Divorced Girl Smiling trusted professionals. We cover divorce and dating topics that span from the day you start thinking about divorce, through the entire process to life and love after divorce. Our goal is to arm you with knowledge, inspiration and connections to divorce professionals who can provide you the divorce outcome you want and deserve.

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Let's talk about it

You can ask AI how to get the best possible divorce outcome – or you could ask me!

Let me provide you with firsthand referrals for divorce attorneys, mediators, divorce coaches, financial advisors, real estate agents, mortgage lenders, therapists, and other divorce professionals-some you might not even realize can help you!

Book your free call

No cost. Always confidential

Who Let the Dogs Out?

After spending almost 10 years dating after divorce, Jackie Pilossoph, Founder of Divorced Girl Smiling, has stories. Lots of them.

And now, she’s going public with them in her new book,
Who Let the Dogs Out?