How to Approach Girls: A Letter from Your Middle-Aged Self

Hey, kid.

It’s me—you. Just with a receding hairline, a mortgage, and a slightly better sense of humor. I’ve been thinking about you lately, especially about those years when you were trying to figure out how to talk to girls. You were nervous. Unsure. Always worried about saying the wrong thing, or worse—getting rejected.

So I thought I’d write to you, not to give you some magical pickup line (they don’t exist), but to share a few things I wish I knew back then.

1. She’s a Person, Not a Puzzle

Let’s start here. You’re not “cracking a code.” She’s not a Rubik’s cube of emotions or a mysterious riddle wrapped in a hoodie. She’s a human being with thoughts, feelings, insecurities, and dreams—just like you.

Talk to her like you’d talk to a friend. Be curious. Listen more than you speak. Smile, not because you're trying to charm her, but because you're genuinely glad to be in the moment. Connection begins with respect, not strategy.

2. Confidence Isn’t Loud

You thought confidence was being the center of attention. It’s not. Real confidence is quiet. It’s owning who you are, even the awkward parts. It’s being okay with not being everyone’s cup of tea. (Some people like espresso. Others like chamomile. You can’t be both.)

Confidence says, “This is me. I hope you like me, but if not, that’s okay too.”

And here’s the secret: That energy is magnetic.

3. Rejection Isn’t a Reflection of Your Worth

This one took you way too long to learn.

Not every girl will be into you. That doesn’t mean you’re broken. It doesn’t mean you’re not good enough. It just means she’s not the one for you. That’s it.

Rejection stings. But it also refines. It teaches you resilience. And sometimes, it saves you from the wrong kind of love.

4. Don’t Perform—Be Present

You don’t need a script. You don’t need to rehearse the perfect line. What you need is to be present. Look her in the eyes. Ask her how her day is. Pay attention to what she says. Be there, fully, in the conversation.

Trust me, that matters more than any smooth opener you picked up from a YouTube “dating coach.”

5. The Right One Will Make It Easier

When you meet someone who clicks with your soul, it won’t feel like a performance or a high-stakes game. It'll feel like breathing. Natural. Unforced. Joyful.

You’ll laugh at dumb jokes. Share weird stories. Finish each other’s sentences or sandwiches (both are important).

That ease? That’s a good sign.

6. Work on You, Not Just Your Lines

This one’s big. Instead of spending hours searching for the right things to say to her, spend some of that time becoming someone you like.

Get curious about the world. Learn new things. Follow your passions. Be kind. Be interesting. Be whole.

The more full your life is, the more naturally others will be drawn to it.

So here’s the final word, kid: Girls aren’t a challenge to conquer. They’re people to connect with. And the best connections come when you're not trying to be someone else, but just a better version of you.

You’ll fumble. You’ll say dumb stuff. You’ll trip over your words. And you’ll survive all of it.

In fact, you’ll even look back on it with a smile.

Take care of that heart of yours. It’s a good one.

— You, with more laugh lines and less ego