Gen Z Dating Struggles: Why Flirting Feels Hard (Matchmaker Advice)

You're at a bar. You see someone cute across the room. Your heart starts pounding. You look at them... and immediately look away like a scared dog who just ate chocolate.

Sound familiar?

If you're Gen Z and flirting feels impossible, you're not alone. Professional matchmakers who work with hundreds of singles have noticed something: flirting is in decline, and Gen Z is leading the way.

But here’s the good news: it’s not your fault. And more importantly, it’s fixable. Gen Z dating struggles aren’t about confidence - they’re about a lack of in-person practice.

Why Gen Z Struggles With Flirting Today

Before dating apps existed, meeting people looked very different.

Millennials went to malls. They went to movie theaters for weekend matinees. And when they did those activities, they met people from other schools and neighborhoods. They learned how to talk to strangers. They learned how to get rejected in person.

And here's the thing: rejection in person doesn't sting as much because it happens so naturally. It's not personal. It's just the way people communicate. You learn the social cues of what works and what doesn't.

Early social media platforms like MySpace and Facebook weren't places people dated. They were just ways to communicate with friends. Online dating existed, but it required logging into a desktop computer at home. People weren't walking around with smartphones knowing where every available person was in a five-mile radius.

That changed everything.

The Smartphone Effect on Modern Dating

Once smartphones became ubiquitous, dating shifted. People could suddenly see everyone who was single and nearby. The options felt endless. The rejection became constant - and invisible. And for Gen Z, this digital world has been present from birth.

Smartphones, dating apps, and social media have been part of the entire adult experience. There's never been a time when flirting required showing up without the backup of a screen. There's never been a need to walk up to someone and risk rejection face-to-face because swiping was always an option.

The problem? Dating apps create so much rejection all at once. And when the social muscle to handle rejection hasn't been developed (because practice never happened in person), flirting becomes terrifying.

The Dating App Rejection Cycle

Here's what matchmakers see working with Gen Z clients:

Dating apps promise connection but deliver rejection. Swipe. Match. No response. Or they respond and ghost. Or they ask for a number and never text.

It's rejection layered on top of rejection. And it happens silently, behind a screen, with no context or closure.

This creates a fear of in-person flirting because in-person rejection feels even more vulnerable when someone is already raw from digital rejection.

So Gen Z does what feels safer: nothing. No eye contact. No approaching strangers. No risk.

This is the reality of Gen Z dating - and also the opportunity to do it differently.

But here's the truth: you don't get what you want most in life. You get what you work for. And right now, staying comfortable is keeping people single.

What Flirting Actually Is (And Why You're Overthinking It)

Let's clear something up: flirting is not talking.

No one needs to be witty or charming or have the perfect opening line. Flirting is much simpler than that.

Flirting is eye contact. A quick glance. A small smile. That's it.

Here's how it works:

How to Flirt in Real Life: A Matchmaker’s Formula

Step 1: You see someone cute. Don't stare. Just notice them.

Step 2: Look at them for one second. Make eye contact. Then look away.

Step 3: Keep talking to your friends. Act natural. But after a few seconds, look again. This time, add a tiny smile.

Step 4: Go back to your conversation.

Step 5: Do this for a total of about five seconds across a few glances - not all at once.

What happens next? They'll think they know you. They'll come up and say, "Do I know you from somewhere?"

And just like that, an opening has been created without saying a word.

The Smize: Your Secret Weapon for Modern Dating

The "smize" (smiling with your eyes), is one of the most powerful dating strategies available.

When someone looks at another person with a slight smile that reaches their eyes, they signal interest without desperation. They look confident, approachable, and intrigued.

This is what separates flirting from staring.

A blank stare is creepy. A smize is magnetic.

Practice this in the mirror. Practice it with friends. Practice it on strangers you'll never see again (like someone at the grocery store or coffee shop) just to build the muscle.

The more it's practiced, the less scary it becomes.

Why In-Person Dating Is Making a Comeback for Gen Z

Here's something interesting: apps like Eventbrite are seeing a massive increase in in-person dating events. Comedy shows mixed with speed dating. Cooking classes for singles. Volunteer nights designed for networking.

Why? Because people are craving real connection again.

Matchmakers are seeing more and more singles reject dating apps in favor of activities where they can meet people organically. They want to experience something together. They want to see how someone acts in real life, not just how they curate their online profile.

And the best part? When meeting someone at an event, there's already something in common. Both people showed up. That's an instant conversation starter.

Matchmaker Dating Advice: The Homework Assignment

If you're Gen Z and want to get better at flirting, here's the homework:

Assignment 1: Attend Two Social Events (Not in Your Usual Circle)
Go to a fundraiser. Volunteer at a nighttime event. Take a cooking class for singles. Join an intramural sports league.
Find activities that require networking or socializing with strangers.

Your goal: Practice the eye contact flirting technique. Even if you'd never date these people, just see if it works. See if they approach you.

Assignment 2: Say Yes to Someone You'd Normally Swipe Left On
If using dating apps, stop swiping left on people for reasons that don't matter.
People reject matches because they're wearing the wrong football jersey. Or because their name is the same as an ex. Or because they look "too cool" or "too artsy."

Here's the challenge: Swipe right on one person you'd normally pass on (for a shallow reason). Match with them. Ask them out within 48 hours for a walk and a coffee.

No one needs to marry this person. The goal is to practice showing up, being present, and seeing if there's chemistry in real life.

The Dating Strategy Gen Z Needs: Show Up As Yourself

Here's the matchmaking advice every Gen Z single needs:

The purpose of a first date is not to impress someone. It's to show who you are in this present moment.

No one is trying to win someone over. No one is performing. No one is auditioning for the role of "perfect partner."

People just show up as themselves. A single person. With flaws and quirks and stories.

And the other person shows up as themselves. Also single. Also flawed. Also figuring it out.

Dates three, four, and five? That's when exploration happens: "Here's how you and I could be together."

But on date one and two, it's just learning. Just being present. Just seeing if there's something worth exploring.

When approaching dating this way, the pressure lifts. The need for external validation disappears. Because the question isn't "Do they think I'm worthy?" It's "Do I want to keep learning about this person?"

Flirting Is a Skill, Not a Personality Trait

If you're Gen Z and think you "just don't have game" or "aren't good at flirting," here's what to know:

Flirting is a skill. And skills can be learned.

No one was born knowing how to ride a bike or drive a car or write an essay. Practice happened. Failure happened. Improvement happened.

Flirting is the same.

Start small. Make eye contact with strangers. Smile at the barista. Say "excuse me" to someone attractive and watch how they respond.

Build the muscle. Get comfortable with discomfort.

And remember: you're not looking for everyone to like you. You're looking for the right person to see you.

The rest is just practice.

Ready to Level Up Your Dating Life?

If you're tired of apps, burnt out on rejection, and ready for a real strategy, Agape Match can help.

Book a Consultation→ Create your personalized dating strategy.

Ask a Matchmaker The ultimate guide to dating with intention.

Author

Lucinda Luttrell

Lucinda is a Senior Matchmaker at Agape Match, where she works closely with clients to help them find and foster meaningful relationships. With a keen eye for compatibility and a passion for bringing people together, Lucinda meets with matches, curates connections, and supports clients as they navigate their matchmaking journey.