Are you a Divorced Girl Smiling?


If not, do you want to be one? If you came to this site, you’re one step closer!

Divorced Girl Smiling (DGS) is celebrating!

10 years in business!
7 million pageviews!
78,000 podcast downloads!
A worldwide community of people like you!

Find trusted divorce professionals:

Divorce attorneys, divorce coaches, therapists, financial advisors, real estate agents, mediators, dating coaches, forensic accountants and more. Every one of my DGS divorce professional partners is either someone I work with personally or who I have worked with in the past, or someone who I have vetted extensively. I feel a certain loyalty and obligation to you–my DGS community, when it comes to making referrals to divorce professionals. I take it very seriously, and wouldn’t partner with any professional I didn’t think was ethical, experienced and/or dedicated to their profession.

Read articles on topics that include:

Considering divorce, going through one, co-parenting, dating, sex, finding love again, living life as single parents, and more.

Listen to the podcast!

Download the mobile app!

Join the DGS facebook group!


Divorced Girl Smiling is like going to Starbucks with your friend to talk about your divorce and your love life. DGS is about community — supporting each other, connecting with solid divorce professionals, listening to each other and feeling heard and understood.

My Story:

When I was going through a divorce back in 2007, I felt like I was on an island. I didn’t know anyone who was divorced, I had no family living in my same town, and my kids were 3 and 5. At 41 years old, I felt more alone than I ever had in my life. It was depressing and sad and embarrassing. I felt like everyone was talking about me and no one wanted anything to do with me.

I cried several times a day, I was angry, and felt bitter, cheated, scared, old and hopeless. I felt like things would never change, and like I would end up a lonely old woman. Back then, I wish I would have had a community–people to talk to, people who understood how I felt, and people to validate me. To say things like, “I know how hard this is,” “You have every right to be a basket case,” and “I am here for you, even if you want to reach out at 3am when you can’t sleep.”

That’s why I started Divorced Girl Smiling. I didn’t want anyone to feel alone and isolated. This site is my way of giving back to those who are where I was all those years ago, and to share what I know–what I did wrong and what I did right. I’m also here to connect you with divorce professionals who can help you practically and emotionally, and to give you hope that you will end up happy. I promise you, you will.


Divorced Girl Smiling Trusted Partners


My life isn’t perfect, but it is GREAT. I have a wonderful mission (Divorced Girl Smiling), two amazing young adult children and a man I love so deeply my heart hurts. Getting here wasn’t easy and it took time, but it happened and it will happen for you, too if you: have patience, believe in yourself and make good, ethical decisions moving forward. Of course you will make mistakes and do some dumb stuff on your journey. It’s OK. I can’t count the number of mistakes I made. That’s part of life.

So, feel free to grab a cup of coffee or tea, or a glass of wine, and browse the site anytime of day or night. I’m here for you.


Listen to the Divorced Girl Smiling podcast


What Divorced Girl Smiling Isn’t:

  • A man-hating site

  • A pity party

  • A place where I promote divorce – I’m a romantic at heart and truly love the idea of marriage (but only if you’re with the right person).

I’ll leave you with a really funny divorce memory I have. When I was first going through my divorce and feeling the worst about myself in every way, my then 4 year-old daughter walked into my bathroom just as I was getting out of the shower. She looked at my naked body and asked, “Mommy, why are your boobs so ugly?” Great. Just what I needed. Like I didn’t have enough self-esteem and bad body image issues. But, the point of this story is, if you don’t laugh, you’ll just cry. So, choose laughter!

I wish you all the best in health, wellness and happiness in your journey ahead!

With love,

Jackie Pilossoph
Creator and Editor-In-Chief, Divorced Girl Smiling


My guest appearance on The Weekly Show on iHeart radio with Melissa Forman:

My bio:


Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling, the website, podcast and mobile app. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also created and wrote the weekly dating and relationships advice column, “Love Essentially”, which was published in the Pioneer Press, The Chicago Tribune and all other Tribune Publishing publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University, and spent time as a broadcast journalist at KTTC in Rochester, Minnesota, as well as several years writing feature stories for the Pioneer Press/Chicago Tribune. She lives in Chicago with her family. Oh, and she’s divorced. Email Jackie at:

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