7 Dating Tips To Turn Your First Date Into Many Many More

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

dating tips

There’s nothing worse than sitting by the phone waiting for a guy to call after a first date. Sometimes you never hear from him and wonder ‘what went so wrong?’ In my Love Essentially column, published in Chicago Tribune Pioneer Press, I offer 7 dating tips that will help increase the chances of your next first date turning into a a lot more!

7 Tips To Turn a First Date into Many Many More by Jackie Pilossoph

We’ve all been there. You’re sitting across the table from someone who you think is close to perfect. Smiling from ear to ear, you sip wine and barely eat as you gaze into his or her beautiful eyes, unable to believe that after countless awful dates, you actually met someone who stopped your world.

I’m describing a really, really great first date. Unfortunately, no one gets too many of those, as lots of first dates end in disappointment, irritation, and nightmare stories you end up sharing with your friends. So, how can you turn a first date into many, many more?

With the help of Erika Kybartas, a matchmaker for It’s Just Lunch in Chicago, we came up with seven tips we think will improve your chances.

1. Dress to Impress: “Before you leave the house for any date, look in the mirror and say, ‘Would I want to date me?'” said Kybartas, who has been in the business for 14 years, estimating she has set up thousands of couples during that time, hundreds which have resulted in long-term relationships. According to Kybartas, dress code for a dinner date is jeans, a nice top and heels, or a dress if you prefer. For men, she recommends business casual: jeans, a nice pair of shoes, a button down and sport coat. If coming to the date straight from work, a suit is acceptable. “Look like you put some effort into your outfit,” Kybartas said.

2. Choose the right venue: Keep first dates casual and short in length. Drinks and appetizers, lunch or coffee are great options. Wait for a second or third date to do something more active or that will result in spending a longer amount of time together. Great second or third dates include golf, tennis, a museum, or a paint and sip studio.

3. Be open-minded: “You can’t change a bad personality, but you can always change a bad T-shirt or an unlikable mustache,” Kybartas said. In other words, if you’re a little bit unsure, keep talking! Keep asking questions and getting to know the person. You might just fall in love, and can then talk to him or her about superficial changes later.

4. Talk is important: Good topics for a first date: common interests and lighthearted subjects that make you both laugh. Bad topics: money, finances, religion, politics and past relationships. Also, if you start talking negatively about your ex, or call him or her a name, I can guarantee you will never hear from your date again. Ever.

Click here to read the rest of the article (the other 3 tips) published in Chicago Tribune Pioneer Press!
Buy novels by Jackie Pilossoph



Featured Expert Articles

Jackie Pilossoph Jackie Pilossoph
Creator, Editor-in-chief, Divorced Girl Smiling
20 Things I Wish I Could Have Told My Newly Separated Self

20 Things I Wish I Could Have Told My Newly Separated Self

Elaine Koby Mossr Elaine Koby Moss
Vice-president and Senior Advisor, Vestor Capital
Want Financial Security After Divorce? Here’s Your Checklist

Want Financial Security After Divorce? Here’s Your Checklist

Dan Stefani Dan Stefani
Divorce Attorney, Principal, Katz & Stefani
Thinking About Divorce? Here Is Your Legal Consultation

Thinking About Divorce? Here Is Your Legal Consultation

Jeremy Woods Jeremy Woods
Senior Residential Mortgage Banker, CIBC
Your Mortgage And Divorce: 4 Reasons To Refinance ASAP

Your Mortgage And Divorce: 4 Reasons To Refinance ASAP

Leslie Glazier Leslie Glazier
Real Estate Agent, @properties, Certified Real Estate Divorce Specialist
Hiring a real estate agent

11 Questions To Ask When Hiring a Real Estate Agent During Your Divorce

Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. 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.

One Response to “7 Dating Tips To Turn Your First Date Into Many Many More”

  1. Tina

    Great suggestions…when you haven’t been on the dating scene in so long , it can be extremely overwhelming. It’s a whole new thing for sure one that is not to be taken lightly. As a woman I just want to feel safe mostly; the rest can be understood and see how it goes.


Leave a Reply

Your email address will not be published. Required fields are marked *