What is
Divorced Girl Smiling?

It’s a place that connects people facing divorce with trusted, vetted divorce professionals, and it is meant to empower and inspire you through your divorce and after.

Celebrating...
Celebrating...

12 years
in business

7 Million
page views

Over 190k
Podcast Downloads

A worldwide community
of people like you

Divorced Girl Smiling

Welcome to the community! Divorced Girl Smiling is all about helping you feel like you’re part of a supportive, loving, caring community. The community is both those facing divorce and dedicated and trusted divorce professionals.

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.

What people are saying about Divorced Girl Smiling

“Everything you write about I have experienced. And it’s all unfolding as you explained. Thank you again for all that you do.”

“I simply cannot express in words how valuable you are to the divorce community.”

“Your site has gotten me through some really difficult nights. Seriously, you should be a therapist.”

“If not for your articles I could not have gotten through the last 2 1/2 years so gracefully. Thank you beyond measure.”

“Divorced Girl Smiling has been a big comfort and a source of direction for me in a very confusing and upsetting time.”

What’s 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!

DGS 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.

Visit the Divorced Girl Smiling Trusted Professionals page

My story

Then and Now

When I was going through a divorce in 2007-2008, 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 other divorce professionals. In fact, I didn’t even know what professionals 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.

Grab a cup of coffee, 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.

Birthday and concert

What Divorced Girl Smiling Isn’t:

  • A MAN-HATING SITE
  • A PITY PARTY
  • A PLACE WHERE I PROMOTE DIVORCE – l’m 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

Big News

Mark Cuban Joins Divorced
Girl Smiling’s Mission to Empower

Divorced Girl Smiling is proud to share that Mark Cuban, billionaire, entrepreneur and Shark Tank shark is an investor in Divorced Girl Smiling. Mark is happily married, but understands and shares Divorced Girl Smiling’s passion to empower and inspire people facing divorce. How did this come about? I’ve known Mark my whole life. Our families are dear friends. If you ask anyone who knows me, they’ll tell you that 11 years ago when I started Divorced Girl Smiling, I would tell people, “My goal is to have Mark Cuban as an investor in this company one day.”

I am thrilled it came to be.

In the media

WGN9

On the WGN Morning News to Talk About Dating After Divorce

Daytime Chicago

Talking About Dating After Divorce on WGN's Daytime Chicago

Vogue

My Quote in Vogue's "Are you a Hopeless Romantic? Here are the Signs."

Love Essentially - Chicago Tribune

My Love Essentially syndicated column, published in the Chicago Tribune

HuffPost

My Articles and Interviews for the Huffington Post

Dancing

My Performance for the Glenview Education Foundation's “Dancing with the Local Stars”

The Weekly Show 93.9 FM

My Guest Appearance on The Weekly Show on iHeart Radio with Melissa Forman

The Good Men Project

My Articles for The Good Men Project

Better

My Articles in Better Magazine

Live Fit Magazine

My Articles for Live Fit Magazine

National Association of Divorce Professionals

My Article for the National Association for Divorce Professionals

DatingAdvice.com

My Article for DatingAdvice.com

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?