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Worst Divorce Moments with Jackie Pilossoph

jackie pilossoph

What happens when worst-case-scenarios come true? Jackie Pilossoph offers real talk about some of the worst divorce moments ever, plus real-world advice about how to work your way through, perhaps even with grace and a smile on your face.


Jackie found herself divorcing when her kids were just 3 and 5 years old. Despite multiple attempts to solve the issues that divided her and her husband, things simply didn’t work out. When even couples’ therapy failed, Jackie and her ex-husband realized that divorce was the best option.



Nobody expects their marriage to end in divorce. For most people, it’s as traumatic and heartbreaking as it was for Jacki. As she navigated the murky waters of her divorce, she felt like she was an island as she was the only person in her circle who had faced the emotional pain of divorce. Having no one to talk to made matter worse and when it was all over, Jackie realized that she didn’t want others to experience divorce in the same lonely space she did. That’s when she decided to create her blog, Divorced Girl Smiling.


In This Episode

Jackie discusses with Jennifer the value of friendship and laughter while working one’s way through the worst moments of divorce. During the conversation, Jackie touches on some of the toughest topics and provides practical advice for surviving divorce and everything that comes after, including:

  • Dealing with feelings that arise when your ex has a brand-new relationship even though it only feels like you separated moments ago. Why do new relationships happen so soon? What does it mean for you and your future?


  • Fear of the unknown and dealing with the stress and anxiety that happen when you’re not sure what’s going to happen next.


  • What happens when you compare your situation with others, and the importance of creating your own happily ever after.


  • Encountering reminders of your past and what they meant to you during your marriage vs. the way they make you feel now; for example, dealing pragmatically with wedding and engagement rings after divorce.


  • The ins and outs of dating after divorce: The way we meet new people has changed, our bodies have changed, and our entire outlook on dating and life has changed, too. New relationships can be terrifying and exciting, all at once but in general, your new contacts will be of better quality than they were when you were much younger.


  • Not every date has to end in a new relationship. Go into dates with the expectation of learning, growing, making new contacts, and creating friendships. Hunting for husband #2 can end in disaster. Making new, meaningful friendships adds richness to your life.


  • The importance of being ready for next steps rather than forcing issues. There’s no need to settle for anything that isn’t right for you.


  • Be patient during divorce; the entire process can take more than a year. Make good decisions and don’t settle for less than you deserve.


  • Remember that your life doesn’t need to be placed on hold simply because you’re going through divorce. Even though it feels like divorce feels like the center of your universe, there’s far more to life than these difficult moments.


  • Be kind to yourself. Love yourself and don’t be too hard on yourself. Allow yourself to cry, get together with friends, and work on areas that you’d like to improve. Growing and learning means you emerge from divorce happier than you ever imagined.


  • Anything that can bring levity to the situation is valuable. While laughter and friendship don’t stop – cultivating a sense of humor will help you make it through even the worst parts of divorce and emerge transformed, with fresh perspective.

About Jackie Pilossoph

Jackie Pilossoph, founder, creator, and editor-in-chief of the blog Divorced Girl Smiling, which is dedicated to providing support, resources, and a much-needed dose of laughter to anyone separating, divorcing, or living life after divorce. Jackie is also the author of two novels: Divorced Girl Smiling and Free Gift with Purchase. She writes a weekly dating and relationship advice column called Love Essentially.



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