Dating Advice: A Tiny Tip That Could Improve Your Love Life

By Jackie Pilossoph, Creator and Editor-in-chief, Divorced Girl Smiling site, podcast and app, Love Essentially columnist and author

In this week’s “Love Essentially” column, published yesterday in Sun-Times Media Local,I wrote about an experiment I did that involved lipstick. The results were astounding, and I think they make a strong statement that could translate into some really good dating advice.


The Lipstick Experiment Boosts Self-Confidence by Jackie Pilossoph


The idea for this week’s column began when I was buying a pair of earrings in Bloomingdales. The cheerful woman who rang me up looked absolutely beautiful. Not fake, made up, skinny model beautiful, but cheerful, happy, healthy pretty. She had these bright pink lips that lit up her face and enhanced her smile.

That’s when it hit me. A small item that doesn’t cost very much money and that takes three seconds to apply can make a huge impact on a woman’s physical appearance.

Never much of a lipstick gal in the past, I dashed straight to the makeup counter, began trying on colors, and 12 minutes later walked out the door wearing Bobbie Brown’s “Berry Punch,” and carrying my new lipstick in a small bag.

This began “The lipstick Experiment,” where I decided to wear my new lipstick religiously for 10 days to see if and how it would make a difference in my life. I wore the lipstick everywhere I went, with the exception of the gym. I wore it even if I had on no other makeup, and even if my hair was in a ponytail and I had on old jeans and sneakers.

The results of this experiment were so much more dramatic than I ever expected! Here are some of the things that happened to me during the 10 days:

1. A woman at the grocery store stopped me and told me I had beautiful eyes. I was not wearing any eye makeup.

2. A friend of mine who I ran into at my kids’ school asked me what brand and color lipstick I was wearing. She then pulled out her iPad and typed in the information.

3. One morning, I was getting some work done at a Starbucks, and realized I forgot to put on the lipstick. I went to the bathroom and applied it, came back to my seat, and the guy sitting next to me did a very obvious double take.

4. I was then walking out of that same Starbucks and a different guy, (who looked a lot younger than me) was walking to his car and kept turning around and smiling at me. I swear I’m not making this up.

5. I was covering an event for Sun-Times local and a woman I know was there. As I was taking pictures, she turned to me and said “Something is different. I think it’s your hair. You look so young.”

6. Other comments I got from friends included, “You look so gorgeous,” “You look tan. Did you just get back from vacation?” and “You look so happy.”

7. My favorite story was the very nice looking guy in the Home Depot parking lot, who kept smiling at me, to the point I had to pretend I was on phone so he would get in his car and drive off!


I hope I don’t sound conceited by these stories. They are factual, and quite honestly, shocking. What I learned from “The Lipstick Experiment” was that even more importantly than LOOKING brighter and better, wearing lipstick made me FEEL brighter and better. For those 10 days, I think I exuded a certain self-confidence I don’t normally have in regards to my physical appearance. It’s a lesson to all women: If you think you are beautiful, and you walk around proud of who you are—both on the inside and out—it will show in your posture, your poise and your demeanor, and you will become more attractive to others.


I couldn’t resist contacting Northbrook based makeup artist, Elise Brill, (who has been in the business for over two decades) to ask for some lipstick tips, since I know this article might prompt many women to try “The Lipstick Experiment,” and “Berry Punch” isn’t for everyone. Here are Brill’s tips.


1. Don’t buy a lipstick without trying it on. Walk around the store for awhile to determine if you feel pretty in it.
2. Dark lipsticks can be pretty, but if it’s too brown, it can make your teeth look yellow.
3. Just because you love the way a lipstick looks on your friend, that doesn’t mean it will look good on you.
4. Always wear lipstick when having your photo taken. It will enhance your smile.

Buy novels by Jackie Pilossoph



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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorced Girl Smiling is here to empower, connect and inspire you. Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling, the site, the podcast and the app. A former television journalist and newspaper features reporter, Pilossoph is also the author of four novels and the writer of her weekly relationship column, Love Essentially. Pilossoph holds a Masters degree in journalism and lives in Chicago with her two teenagers. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

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