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!
Over 130K podcast downloads!
A worldwide community of people like you!

What is Divorced Girl Smiling? It’s a place that connects people facing divorce to trusted, vetted divorce professionals, and it is meant to empower and inspire you, too.

What is the best way to increase your chances of having the divorce outcome you want and deserve?

Hire vetted, trusted divorce professionals.

Here are the Divorced Girl Smiling trusted divorce professionals!


Divorced Girl Smiling Trusted Partners


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.

What’s the best way to feel empowered?

 Listen to the podcast!

Read articles on the DGS website!

Download the mobile app!

Sign up for the DGS FREE Consult!

Join the DGS facebook group!


Divorced Girl Smiling (DGS) is like going to Starbucks with your friend to talk about your divorce and your love life. DGS is about community — the community is those facing divorce and those who have dedicated their careers to helping people in your shoes.

DGS is about offering support, listening,  and helping you feel heard and understood. It’s about meeting and connecting with some of the best divorce professionals in the industry, so that you end up with a divorce outcome that makes you happy and keeps you healthy.

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, and I didn’t know how to find a divorce attorney, or the other divorce professionals I didn’t even know I needed!

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, professionals who truly cared, 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, and who I should have connected with professionally. In divorce, there are a lot of things you can’t control–your ex, his lawyer, and the judge in your case, to name a few. What can you control? Yourself, how you choose to tackle this battle, and the professionals you surround yourself with–people you trust and who have your back. 

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 listen to the podcast, check out my trusted divorce professionals, 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
Founder, Divorced Girl Smiling

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

My articles for the Today Show:

Dating after Divorce? Take This Advice from a Relationship Expert

What is Relationship Cycling? Plus, How to Avoid It

My Love Essentially syndicated column, published in the Chicago Tribune:

Read my columns here.

My performance for the Glenview Education Foundation’s “Dancing with the Local Stars”



My articles for the Good Men Project:

Read my articles here.

My articles for the Huffington Post:

Read my articles here.

My appearance on You & Me:

My articles in Better Magazine:

Read my articles here.

My articles for It’s Just Lunch:

Read my articles here:

6 Tips to Get Your First Date Conversation Flowing

7 Dating Tips for Single Moms

My articles for Live Fit Magazine:

Read my articles here.

Quoted in Newsweek articles:

Woman Plans to Stay Engaged Forever

Millennial Woman Shares Dating Horror Story

Woman Supported after Blocking Date Following $500 Meal

Why Some Americans Want to Get Divorced–But Can’t

Gen Z Women Delete Dating apps within a Month: “It’s a Waste of Time”

What I’ve Learned From Working in the Divorce Business for 11 years


My bio:


Jackie Pilossoph is Founder of Divorced Girl Smiling, (DGS), the company that connects people facing divorce with trusted, vetted divorce professionals.  DGS is also a 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 6 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. Additionally, Pilossoph was a Huffington Post blogger for 3 years. She lives in Chicago with her family. Oh, and she’s divorced. Email Jackie at:


Listen to the Divorced Girl Smiling podcast View the DGS trusted divorce professionals! Divorced Girl Smiling is now offering a private, no-cost, one-on-one phone consult

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