Let me ask a simple question: Did dating apps actually make dating better?
Because I'm starting to think we may have confused making dating easier with making people better at dating.
Those are two completely different things.
Dating apps made it easier to find somebody. Social media made it easier to get somebody's attention. DMs made it easier to make the first move without actually having to make the first move.
But somewhere along the way, we forgot to teach people what to do after somebody says yes.
And apparently, a lot of young men never got the memo.

Back When Asking Somebody Out Took Courage
Think back 20+ years ago. Middle school dances.
The gym would be decorated with whatever the school could afford. Some DJ was playing music that sounded much better than it actually was. Somebody's mother was standing along the wall watching everybody like she was running surveillance for the FBI.
And then there were the boys on one side of the gym.
And the girls? On the other side.
A boy could stand there with his friends, pretending he was perfectly comfortable while secretly trying to figure out which girl he was going to ask to dance.
And then came the moment... He had to walk across that entire gym floor.
Not send a text.
Not send a DM.
Not like three of her pictures first.
Not watch her Instagram story for six months hoping she would somehow understand that he was interested.
He had to walk over there and open his mouth.
"Would you like to dance?"
That's it. Five words.
But those five words could feel like you were preparing to address Congress.
And if she said "no"? You had to walk all the way back in front of everyone.
And your boys were waiting. "Man, what happened?"
"She curved you?"
There was no deleting the conversation. No unmatching. No pretending you never asked.
You took the "L" and walked back to your friends.
That was part of growing up. You learned how to approach people. You learned how to handle rejection. You learned that rejection wasn't the end of the world. Most importantly, you learned how to talk to women.

Fast Forward to Today
Now? We've somehow come full circle. Guys still don't necessarily want to approach women. They've just found a way to do it without having to physically approach them.
The DM.
And listen, I'm not going to sit here and pretend DMs are automatically bad. They're not. I asked my wife out through a DM.
I didn't know her personally. We had mutual friends, and we had interacted a little through comments on their posts. So eventually I reached out.
The difference was what happened after she said yes.
When we finally sat across from each other, I knew how to have a conversation.
- I knew what questions to ask to get to know her.
- I knew how to tell her about myself.
- I knew how to make her comfortable.
- I wasn't sitting there staring at my phone trying to figure out what to say next.
And that's where I think we've got a problem.
The Problem Isn't the Dating App
The dating app isn't necessarily the problem.
The problem is what happens when you remove all of the situations that forced people to develop interpersonal skills. If you grow up communicating primarily through a screen, you can become too comfortable communicating through it. That's not the same thing as communicating with a person.
A dating profile gives you information.
A DM gives you an opening.
A dating app gives you a match.
But eventually, the woman is going to be sitting across the table from you and the algorithm isn't coming with you.
That's when the real interview begins.
And apparently, some guys show up completely unprepared.
"So... What Do You Do?"
I've heard enough stories about modern dating to know that some men have apparently reduced conversation to a series of questions that sound like they're filling out an application.
"What do you do?"
"Where do you live?"
"How many kids do you have?"
"What do you like to do?"
Then silence.
BRO!
- You matched with her.
- You pursued her.
- You asked her out.
- You got her to agree to meet you.
Now what?
This is where communication matters. Getting the date isn't the accomplishment. Having a good date is!
You can't spend weeks trying to get a woman's attention and then finally get her in front of you and suddenly become a mute.
That's like a dog chasing a car for three miles and then, after finally catching it, standing there wondering what you're supposed to do with it. You wanted the car! Now drive, Fido!

Dating Apps Have Created a Strange New Problem
Here's the irony: Men have more access to women than ever and yet some men seem less prepared to actually connect with them.
"Hey."
She responds.
Then...
Nothing.
Or worse, the conversation becomes an endless exchange of one-word answers.
"What's up?"
"Nothing."
"What you doing?"
"Chilling."
"Where you from?"
"Memphis."
"Oh."
Really, dude? That's the conversation? We went through all of this technological advancement just to arrive at "Oh."
The Old-School Way Had Its Problems Too
Now, before somebody gets mad and thinks I'm saying everything was better back in the day, calm down. It wasn't. Dating 20+ years ago wasn't some magical romantic paradise.
- People got rejected.
- People got embarrassed.
- People got cheated on.
- People got their hearts broken.
- People also stayed in terrible relationships because they didn't have the options people have today.
And let's not pretend every teenage boy in 1985 was Casanova. Lord knows that I was far from it.
Some of those dudes walked across that gym floor, asked a girl to dance and immediately forgot how English worked.
The difference is that they had to practice.
You couldn't outsource the uncomfortable part. You had to walk over there, speak, and read body language.
You had to figure out whether she was interested. You had to deal with rejection. Then you had to try again.
Those experiences taught you things.
Rejection Used to Be Part of the Training
And maybe that's one of the biggest things we've lost. The ability to be rejected without falling apart has really been lost on younger generation of guys and I blame the parents. Especially the fathers.
If a girl turned you down at the school dance, you survived. You went back to your friends. They roasted you. You laughed it off. And eventually, you asked somebody else.
That experience taught young men something important: The word "no" isn't the end of the world.
It's just "no".
Today, somebody can spend months interacting with women without ever having to experience that same level of vulnerability.
A swipe left doesn't feel the same as standing three feet away from somebody and hearing them say, "No, thank you."
One is an algorithm. The other is person. And people are where the learning happens.
You Don't Need Game. You Need Conversation.
I think we've overcomplicated dating. Men don't necessarily need some secret pickup strategy. They don't need 37 lines they memorized from TikTok. They don't need to pretend they're richer, cooler or more mysterious than they really are.
They need to learn how to have a conversation. Ask questions that actually invite a response.
Listen to the answer. Build on what she says.
Tell her something about yourself.
Make her laugh (that's how I got 'em back then). 😉
Talk about something you're passionate about. Let her see your personality.
And for God's sake, stop treating every conversation like you're trying to get to the next checkpoint in a video game. You're not trying to unlock the "girlfriend" level. You're trying to determine whether two people actually enjoy being around each other. That's the whole point.
So, Are Dating Apps Making Dating Better?
Maybe. For some people, absolutely.
They've helped people meet partners they never would have encountered otherwise. They've made dating more accessible to people with limited social circles and busy lifestyles.
But let's stop pretending that a match equals a connection.
It doesn't.
A match means two people swiped in the same direction.
That's it.
The rest still requires two people who know how to communicate.
And that's the part nobody can automate.
You can have the perfect profile. The perfect pictures. The perfect opening line. The perfect algorithm. But eventually, you're going to have to sit across from that woman.
And she's going to look at you. You're going to look at her. And somebody is going to have to say something.
That's dating.
Maybe the real problem isn't that dating apps ruined dating. Maybe they simply exposed how many people never learned how to do the uncomfortable part in the first place.
Because getting the woman's attention was never the finish line for me. It was just the beginning.
And if you don't know what to say once you finally get there...
Well, congratulations. Just like the dog, you caught the car. Now what?

