Divorced Girl Smiling—Literally!


Divorced Girl Smiling—Literally!

Jackie Pilossoph, divorce and dating writer

Raised in Pittsburgh, Jackie Pilossoph has called Chicago her home for the past 30 years. After a successful career in sales management, and at 30 years old, Pilossoph went back to school for her masters degree in journalism. And so began her second career—that of a mother and writer.

In February 2013, Pilossoph launched her blog, Divorced Girl Smiling, as a way to share lessons she’s learned on her journey from rock-bottom Solo Mom to where she is now: enjoying the happiest, most productive time of her life. Also blissfully happy at finally finding her Mr. Right, she states, “It’s amazing how the heart can bounce back.”

Q: What exactly do you do?

A: I’m a writer! I have a divorce blog called Divorced Girl Smiling and am also a feature reporter and columnist for the Chicago Tribune Pioneer Press (the suburban edition of the Chicago Tribune). I write a weekly dating and relationship column called “Love Essentially.” My most recent books are Divorced Girl Smiling [self-published, 2013] and Free Gift With Purchase [2012]. Clearly, my specialty is divorce and dating.

Q: How did you land in this profession?

A: I was a stay-at-home mom when my kids were young. I wrote Free Gift With Purchase just because I wasn’t working. It had a divorced character, and when the book came out, people started e-mailing me questions about divorce and I thought, I should start a blog. Three years ago, I started Divorced Girl Smiling.

At the time, I was going through some postlitigation issues with my divorce. I was so frustrated that I would just write what was on my mind, and very quickly I realized this isn’t about me; people want me to help them. So I started answering questions and writing about any topic you could think of.

In the meantime, my ex got engaged, got married, my children got a stepbrother . . . all these things happened. I feel like I’ve lived the gamut of divorce and divorced-mom issues—so I write about it. Last month I got 70,000 page views. It’s a full-time job. People are really responding. Today I put out my first video blog!

Q: When and how did you become a Solo Mom?

A: I have a 13-year-old daughter and 14-year-old son. I got married when I was 35 and had kids right away—then realized everything was wrong. We came from such different worlds. We went to counseling but just couldn’t work it out. My kids were three and five at the time, and the thought of being a single mom was scary. My parents had been married forever, so it was foreign to me. Because I didn’t get married until later in life, I wasn’t afraid to be alone, but I was afraid of being the leader of the household—having to make all the decisions without someone to help me raise my two children. For example, once there was a mouse in my house, and I had nobody to help me. Another time the fire alarm went off in the middle of the night. I was so scared. We’re independent women, but we want men to protect us if we need them.

Q: Did being a single mom impact your career?

A: When I was a stay-at-home mom, I wrote novels. I went back to work for the Tribune a few years ago. I’ve always worked out of my home because I want to be around when my kids get out of school. I have so much respect for women who have to go into an office. It must be the hardest thing.

Q: How did you hold up after your divorce?

A: I was frumpy, afraid of everything; I didn’t know how to text; I didn’t know about technology; I hadn’t worked in six years and felt like a total loser. And because I was coming out of a bad marriage, my self-esteem was at an all-time low. Let’s face it—the person you are divorcing isn’t generally complimentary.

Q: How did you turn it around?

A: It was a combination of things: I started doing yoga and working out. I changed the way I ate. And I did what I loved most—I wrote like crazy. It poured out of me. I wrote a novel that’s never been published (because it’s so personal) called I’ve Got Issues; [it’s] about a woman going through a divorce. Whenever I felt hopeless, sad, depressed, angry, scared—I’d just go to my computer and instantly feel better.

In the beginning, I was making bad choices: I drank excessively; I went out partying. I started to make healthy choices. I got it together.

I’m working harder and [more] longer hours than I ever have. I work weekends, holidays, early mornings . . . I have several sources of income, so I don’t know what I’m actually making until I do my taxes. I just did my taxes and feel very proud that I’ve been able to take what I love and make a living at it.

Q: Did you feel a shift in your community when you became a Solo Mom?

A: I just wrote a piece called “9 Facts About the Suburban Single Mom.” Read it!

Some examples include:

  • We don’t hate our friends’ ex-husbands: The divorced husbands of my friends avoid me. They don’t make eye contact at the gym because they assume I hate all men—because I’m divorced.
  • We don’t milk it: we attempt to keep up with carpooling, but if we can’t do exactly the same amount as the wealthy, married woman with staff, cut us some slack.
  • We are no longer included: if friends have a dinner party with couples, I’m not in.

Q: Was there a defining moment that drove home you were raising children alone?

A: The day my ex moved out, I took my kids to a friend’s house to go swimming so we wouldn’t be there. My kids were too young to notice, but when we came home and walked in, the house was half empty. It was so sad.

Q: How can your site and books help other Solo Moms?

A: My books are strictly for entertainment, though many women find them helpful. With my blog, I feel like I’m helping people and changing lives. I get e-mails every day thanking me. The blog is inspiring and uplifting. It will make you feel like you can fly. You can do it! My blog is like going to Starbucks with a girlfriend and talking about your divorce and your love life.

Q: Of what are you the most proud about yourself as a Solo Mom?

A: I feel like I’m living a life I never thought I was strong enough to live. It sounds corny, but remember that Whitney Houston song where she sings, “Give me one moment in time when I’m more than I thought I could be”? That’s how I feel. It’s not always rosy, but I’m proud of how I live my life, how I raise my kids and run my household, while enjoying myself immensely.

Q: Favorite solo-parenting tip?

A: Three or four times a week I have a sit-down dinner with my kids. We put away our cell phones, and we talk. It’s something they’ll always remember, and then do with their families. It’s not something you have to cook to do. Even if I get McDonald’s, we still sit together to eat it . . . like filet mignon.

You can follow Jackie on Facebook, Twitter, and Instagram.


Kathleen Laccinole, ESME’s Dating Resource Guide, has penned numerous films and parenting books but is best known for producing the highly lauded Greta, age 20, and William, age 16.

Please feel free to contact us with any comments or questions.


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