I’m not a dating expert. I’m just a guy who spent three years on every app you can name – Tinder, Bumble, Match, Hinge, Coffee Meets Bagel – and made every mistake in the book.
Actually, let me be more specific. I made the same mistake five different ways, with five different women, before I finally figured out what I was doing wrong.
The mistake? I was trying too hard to be “interesting.” And it was killing my chances.
Here’s what I learned.
The First Time I Screwed Up – The “Interview” Approach
There was this woman named Sarah. She was gorgeous. She had these photos from a trip to Thailand that made me feel like I’d never actually traveled anywhere. She was a graphic designer with a sarcastic sense of humor that came through in her bio.
I sent her a message that was basically a job interview:
“Hi Sarah! I see you went to Thailand. I’ve always wanted to go. What was your favorite part? Also, what kind of graphic design do you do? I’ve always been curious about the field.”
She replied. She was nice about it. She answered my questions. And then I asked more questions.
“Where else have you traveled? What’s your favorite color? Do you have any pets?”
She stopped replying after three messages. I can’t blame her. I wasn’t having a conversation with her – I was interrogating her. I was so focused on “showing interest” that I forgot to share anything about myself.
What I should have done:
Instead of just asking questions, I should have shared something too. A conversation is like a tennis match – you have to hit the ball back, not just keep serving. I should have said:
“That photo of you in Thailand is incredible. I’ve actually been wanting to go, but I’m terrified of the food – I can barely handle a jalapeño. What’s one thing you’d tell a nervous traveler to try?”
That’s still showing interest, but it’s also giving her something to work with. It’s sharing a weakness, which makes you seem human.
The Second Time I Screwed Up – The “Compliment” Trap
Then there was Emma. Emma had this stunning smile in every photo. She looked warm and approachable. So I decided to be straightforward and lead with a compliment:
“You have a beautiful smile. I’d love to get to know you.”
I thought this was nice. I thought it was honest. But here’s the thing: Emma had probably received a hundred messages just like that that week. She didn’t respond.
I sent a follow-up three days later. The message was something like, “Hey, just checking in.” And she replied with a short, polite “Hi.” That conversation didn’t go anywhere either.
What I should have done:
A compliment isn’t a conversation starter – it’s a dead end. I should have gone with something playful and personalized:
“Okay, I have to ask – what’s the story behind that photo of you in the giant inflatable unicorn? That’s not a thing people just casually do.”
She would have laughed. She would have told a story. And I would have actually learned something about her, instead of just using a line.
The Third Time I Screwed Up – The “Grocery List”
The third one was a woman named Jess. She had a great profile. She was into hiking, cooking, and had a photo in an indie bookstore that I could have stared at for hours.
I didn’t just send one message – I sent three. In a row. Without waiting for her to reply.
“I love hiking too, what’s your favorite trail? Also, that bookstore looks amazing. And I see you’re into cooking – I make a mean pasta.”
It was like I was trying to impress her with my “compatibility” by listing all the things we had in common. But it came across as desperate and overwhelming. I was trying to prove that we were a good match before we’d even had a real conversation.
She never replied. I don’t blame her. I was trying too hard.
What I should have done:
I should have sent just one message. One thoughtful, specific message that showed I’d actually read her profile.
“Hey Jess – that bookstore in your photo, I think I’ve been there! Is it the one with the cat in the window? I swear that cat gave me a dirty look when I tried to pet it.”
That would have been enough to start a conversation. Just one thing. Not three.
The One Time I Got It Right
After all those failures, I finally figured out the formula. Not a “line” – a formula. And it worked.
I matched with a woman named Tessa. She had a photo at a music festival. She mentioned in her bio that she “will always stop to pet a dog.” And she had a slightly awkward laugh, which she admitted in her prompt.
I thought about what to say for maybe 15 seconds. Then I wrote:
“I have a question that could determine your entire moral character. Do you pet the dog, or do you ask the owner first? I’m a ‘pet first, ask later’ guy, and I’ve been bitten twice. I still haven’t learned.”
It was a small message. It didn’t have anything fancy. But it was personal, playful, and had a little vulnerability. Tessa responded within a few hours. We’ve been together for over two years now.
The formula is simple:
- Read her profile carefully
- Pick one specific thing
- Comment on it, ask a follow-up question, and throw in a personal detail (maybe an embarrassing one)
- Don’t overthink it
- Send just one message
What I Learned
I was trying so hard to be the perfect guy that I forgot to just be a person. Women don’t want to be interviewed. They want to be connected with. They want someone who’s not trying to prove anything.
Some things that will change your messaging game:
- Pick one thing, not three, not five. Don’t list all your shared interests.
- Ask a question, but share something too. Don’t just interview her.
- Have a little vulnerability. It’s okay to admit you’re awkward or nervous.
- Don’t double message. Don’t send a second message before she replies, unless it’s been a few days.
- Write like you talk. Don’t try to sound like a novelist.
