7 Lessons on Love from the Digital Matchmaker

It’s not a legal holiday, and it’s not a Hallmark holiday. August 31 is National Matchmaker Day, a day to celebrate the matchmakers and modern-day Cupids devoted to helping singles find love.

So, to all my fellow matchmakers passionate about making introductions, creating connections, and spreading the love, I celebrate every one of you today.

For me, National Matchmaker Day is also a day to reflect on the many years I’ve spent in the business of love, and the singles who have trusted me with something incredibly precious: their hearts.

I’ve watched dating change dramatically over more than three decades. As an early adopter of the internet, I was there in the earliest days of online dating, long before swiping became a verb. Having watched dating sites turn into dating apps, algorithms become more sophisticated, and now AI has become part of the way singles date, flirt, and search for love, there’s one thing I’m certain of:

Technology has changed almost everything about how we meet, but it hasn’t changed why we meet.

Singles still want to love and be loved. They still get butterflies when someone special walks into the room, or when a text arrives from someone they like. After a great first date, they still wonder whether their match felt the same spark.

And they’ll always have hope that somewhere out there, there’s a person who will make them very happy they didn’t give up on love.

Last year, on National Matchmaker Day, I took you inside my world, from dating coaching to becoming relationship-ready, to ultimately finding a match worth pursuing.

RELATED: National Matchmaker Day: Inside the Digital Matchmaker’s World

This year, I’m celebrating the day a little differently.

After Dolly Parton’s passing, I couldn’t stop thinking about what she taught us about love. Her nearly 60-year marriage to Carl Dean was famously private, but the love, humor, independence, and devotion they shared endured through an extraordinary life and career.

In Love Lessons from Dolly Parton, I wrote about some of her lessons that will stay with us and how they can inspire our own relationships.

RELATED: Love Lessons from Dolly Parton

As I was writing it, I realized how many of those lessons were familiar to me. I’ve seen them play out repeatedly in my work with singles, both before they find love and after they do.

So, on National Matchmaker Day, I’m sharing seven love lessons I’ve learned along the way.

1. Be True to Yourself

Dolly certainly knew how to make an entrance, but underneath the rhinestones, wigs, and one-liners was a woman who always seemed to know exactly who she was.

There’s a dating lesson in that.

Of course, you should always put your best foot forward on a date. But there’s a difference between showing up as your best self and becoming the person you think your date wants you to be.

If you love getting dressed up, don’t pretend you’d rather spend every weekend hiking or camping just because you think that’s what your match wants to hear. If something is important to you, don’t minimize it because you’re afraid your date might disagree.

And don’t spend so much time trying to impress someone that you forget what I remind my clients every day: you’re the prize.

The goal of dating isn’t to be irresistible to everyone. It’s to meet the person who likes the real you.

2. Lead Beyond the Checklist

A good holiday gift list works because you already know the person. A dating checklist is different. Treat it as gospel, and you risk ruling out someone who ends up finding love with a person more open-minded than you were.

Still, creating a checklist has value. There are the non-negotiables, the deal-breakers, and then the wish list that can become very long: age, height, education, career, location, lifestyle, politics, interests, and sometimes even hair color.

I believe in knowing what you want, especially when it comes to values and relationship goals. But I’ve also learned that the person who looks perfect on paper isn’t necessarily the person you’ll fall in love with.

Part of my job as the Digital Matchmaker and a certified dating coach is sometimes to say, “I know this isn’t exactly what you asked for, but I think you two should meet.”

That’s not settling. It’s being open to the possibilities.

And don’t let geography shrink those possibilities before a connection even has a chance to begin.

So many singles are working remotely now, while others are retired or ready for a new beginning and have more flexibility about where they live. That’s why I always recommend casting a wide net.

People have crossed oceans and moved mountains in the name of love, and one king even gave up his throne. So don’t let a ZIP code keep you from starting a conversation with someone who might get you.

You don’t have to hire a moving truck tomorrow, or slam the door shut. You just need to be open enough to see whether the connection is worth exploring.

3. Stay Curious

This was one of my favorite lessons from Dolly, and it belongs on every first date.

I tell singles to arrive with curiosity rather than an interrogation list. Put your phone away. Ask questions because you want to hear the answers. If your date says something interesting, follow up on it instead of mentally moving on to the next question.

There’s a big difference between trying to determine whether someone checks your boxes and taking the time to get to know them.

You don’t have to decide over appetizers whether the person sitting across from you could be your forever person. The goal of a first date is quite simple. Decide whether you want to schedule a second date. That’s it.

For an hour or two, just be present. You might be surprised by what you learn.

4. Chemistry Matters, but Green Flags Matter More

Of course, chemistry matters, and I’m certainly not going to argue against butterflies.

I’ve seen what happens when singles become so focused on an immediate spark that they overlook everything else or dismiss someone wonderful because the first date didn’t feel like a scene from a romantic movie.

Attraction can grow. And sometimes the person who gives you instant fireworks isn’t the person who can give you the relationship you want.

Kindness, shared values, emotional availability, communication, consistency, and wanting the same kind of future become increasingly important as a relationship develops.

It’s OK to want the butterflies. Just don’t let them outvote the green flags.

Kindness, consistency, and shared values are what build a relationship with staying power.

RELATED: Clarity Green Flags: How Aligned Dating Feels (No Coding Required)

5. Keep Your Sense of Humor

Dating can be exhausting, but it shouldn’t feel like you’re stuck on a hamster wheel of uncertainty.

If you take every disappointing date personally, the whole process can start to feel discouraging very quickly.

Dolly understood the power of humor, including the ability to laugh at herself. That’s a quality that serves singles well, too.

Sometimes the best thing you can do after a date that went sideways is laugh about it, learn from it, and move on.

And when you do meet someone special, keep laughing.

Some of the happiest couples I know genuinely enjoy each other. They have private jokes, tease each other, and can find humor even when life isn’t particularly funny.

A shared laugh can be every bit as intimate as a shared kiss.

6. There Is No Expiration Date on Love

I believe this one wholeheartedly.

My grandfather found love at 87 and married his second wife. To me, he was the perfect example of a second-chapter love. I’ve worked with singles who are dating after a gray divorce, after losing a spouse, after heartbreak, and after living alone for years. Some arrive excited about finding love again. Others quietly wonder whether their chance has already passed.

I’m here to tell you not to give up on love, at any age.

There is no expiration date on butterflies, companionship, romance, or the possibility of meeting someone who makes your life even richer.

You can have a full, independent life and still make room for someone special.

RELATED: 10 Golden Lessons on Love at Any Age

7. Never Underestimate One Introduction

After all these years, this is still my favorite part of matchmaking.

Two people can live in the same city, go to the same restaurants, know some of the same people, and never cross paths.

Then someone says, “I know someone I think you should meet.”

The first conversation may last 20 minutes, or it may last for hours. Then it’s time for a first date, and if all goes well, a second one.

And sometimes, much later, I get the call. They’re exclusive. They’ve fallen in love. They’re engaged, moving in together, or getting married. Those are the calls that never get old, and you’ll find many of those love stories on my testimonial page.

Every relationship has a beginning. Sometimes an entire love story can be traced back to one person who believed two people should meet. Perhaps that person is a friend. And sometimes, it’s a matchmaker

Celebrating the Matchmakers Who Keep Spreading the Love

Matchmaking is personal and rewarding work. We make introductions, encourage singles through the ups and downs of dating, and celebrate when a connection turns into something more.

Not every match becomes a love story, but the next one might.

So, on National Matchmaker Day, I’m raising a virtual glass to my fellow matchmakers who keep spreading the love, and to the singles who have trusted me with their hearts over the years: thank you.

My wish is simple: more introductions, more possibilities, and more love stories.

Happy National Matchmaker Day.

Julie Spira is the Digital Matchmaker® and America's Top Online Dating Expert. She's an award-winning certified dating coach who's been helping singles find their perfect match for over three decades. Follow @JulieSpira on IG and @digitalmatchmaker on TikTok.