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 a safe, anonymous place for men and women to come and browse articles written by me and some other divorce experts and professionals on topics that include: considering divorce, going through one, co-parenting, dating, sex, finding love again, living life as single parents, and more.

DGS is also a great place to discover professional resources (divorce attorneys, therapists, financial advisors, and more). I have a bunch of DGS partners who I know personally and/or have worked with. I trust each of them and have given careful consideration before referring them to my readers.

My goal is that you feel like going to Divorced Girl Smiling is like going to Starbucks with your friend to talk about your divorce and your love life. DGS is also a community — a supportive, loving and warm place for people to connect with others who are in a similar situation. The Divorced Girl Smiling Group Facebook page, which is free to join is a great place to connect with other men and women going through what you are.

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 support group–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 professionals who can help you practically and emotionally, and to give you hope that you will end up happy. I promise you, you will.


Going Through a Divorce?  Names You Need and Why


My life isn’t perfect, but it is GREAT. I have a great job, a wonderful mission (Divorced Girl Smiling), two amazing teenagers, 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: work hard, 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.

Feel free to grab a cup of coffee or tea, or a glass of wine, and browse the site anytime of day. Divorced Girl Smiling is also a podcast, and coming soon: an app!



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).

Divorced Girl Smiling is a place to come to feel less alone, to feel supported, to find resources, to gather information, to hear other people’s stories, and to receive hope and inspiration for what might seem like a hopeless situation, at times.

Divorced Girl Smiling isn’t just another divorce blog, it’s a community and an honest, non-sugar-coated place to go to get real advice, support, inspiration, more than occasional laughs, and a big hug (which I guarantee you need right now).

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 hope you enjoy Divorced Girl Smiling, and that it makes you feel better, and gives you the motivation to keep going and continue your path towards a new and better life, full of happiness and fun and the best people.

So, are you a divorced girl (or guy) smiling?

In my opinion, being a divorced girl smiling takes self-awareness, good life choices, honesty, authenticity, self-love, patience, and the courage to go out and grab the life you really want. And, being happy often lies in the ability to live in the moment, to laugh a lot, and of course, to give and receive love, no matter what happened in the past.

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 a divorce expert and the creator and Editor-In-Chief of Divorced Girl Smiling, the website, podcast and 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 several years writing feature stories for the Pioneer Press. She lives in Chicago with her family. Oh, and she’s divorced. Email Jackie at:




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