Girl Talk At The Juice Bar: Divorce, Dating, I love You and 50??!!

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

As I was walking out the door yesterday morning, heading to the gym, I got a text from a girlfriend that read, “Whatcha doing? Meet for coffee?” I loved it. No planning, scheduling, cancelling and rescheduling, all I had to do was shift a few things around and an hour later (straight from the gym) I found myself sitting with her in the warm sun outside our local juice bar drinking the ultimate healthy cold-pressed green juice: kale, pear, celery and mint. It sounds gross but it’s actually really good.


What did two divorced moms talk about? Come on in! I’ll tell you.


First we caught up on each other other’s love lives. My girlfriend has been dating a guy for a few months and things are going remarkably well. She’s at the point where she’s considering telling him she loves him, but not sure if she should. So, we decided to weigh the positives and negatives of going for it:




  • Her biggest fear (everyone’s biggest fear, I imagine): he might not say it back.
  • It might scare him and make things awkward.




  • He might say it back right away, which would be ideal.
  • If she’s dying to say it, she will feel a huge sense of relief that she got it off her chest.
  • He might say it back a few hours or days or even weeks later.
  • He will know how she feels and either way, she will know the truth about how he feels.


Here’s the thing about saying I love you first. You have to be willing to say to yourself, “I am telling him I love him because this is how I truly feel. If he doesn’t say it back, I will have no regrets that I said it because it was said with honesty and from my heart. Yes, I exposed myself with the utmost vulnerability I possibly could, but that’s OK, no matter how he reacts.” If you have that attitude, you really can’t go wrong. If you can’t say that, then you shouldn’t declare your love for someone. My girlfriend is going to think about it.


We then shifted to Jackie’s upcoming 50th birthday, which falls on a Thursday night, and should I have a big party for myself? Is that egotistical? The thing is, on my actual birthday, I would like to celebrate with family and friends, eating and drinking and enjoying each other, so why not facilitate it? We then discussed potential venues and times and other details. By the way, if anyone reading this decides you want to have a surprise party for me, please let me know. LOL!


Our last topic of conversation was Divorced Girl Smiling, and what I can do in regards to helping and inspiring others in honor of my turning into an old person. I’m thinking about something like “Doing 50 things I’m afraid to do” and writing about each one over a 6 month period, starting on my bday. What do you think? I’m open to suggestions. Other thoughts I have are “50 set ups” where I fix up 50 couples. Would love to hear your feedback!


In closing, to my dear girlfriend who was happily sipping her kale, red apple and ginger juice and looking up at the bright sunshine (finally here!), her beautiful face taking in the rays, thanks for initiating what was a delightful hour in my day!


There is something truly refreshing and inspiring about girlfriends, their willingness to share, their warm and caring nature, and their ability to make you laugh so hard you spit green juice out of your mouth!

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    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

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