The dating app said we were a 92% match. His profile seemed perfect. Funny bio. Nice smile. Loves dogs and hiking.
Our first message exchange was great. We talked about everything—books, travel, favorite pizza toppings. After two weeks of chatting, he finally asked me out for coffee.
“Saturday at 3 PM?” he texted.
“Perfect,” I replied.
What I didn’t know was that he’d spent those two weeks reading articles about pickup lines. He thought being smooth and using clever bad pickup lines would impress me.
He was so, so wrong.
The Coffee Shop Disaster
I arrived five minutes early. Spotted him immediately—blue shirt, just like he said. He stood up when he saw me, nervously adjusting his collar.
“Hi!” I said, extending my hand.
He shook it, then immediately said: “Do you have a map? Because I just got lost in your eyes.”
I froze. Did he really just say that? Out loud? In public?
“Um, thanks?” I managed.
We sat down. I ordered a latte. He ordered black coffee, hands shaking slightly as he picked up the menu.
“So, you mentioned you work in marketing?” I tried to start a normal conversation.
“Yeah, but before we talk about boring work stuff…” He leaned forward with this weird confident smirk. “Are you a magician? Because whenever I look at you, everyone else disappears.”
Oh no. This was happening. He was using awful pickup lines. Multiple ones.
I glanced at the exit. Maybe I could fake an emergency phone call?
It Got Worse
Over the next thirty minutes, he hit me with five more. Each one worse than the last.
“Is your name Google? Because you have everything I’ve been searching for.”
“Do you believe in love at first sight, or should I walk by again?”
“Are you a parking ticket? Because you’ve got FINE written all over you.”
These weren’t just bad pickup lines. They were terrible. The kind you’d find on the worst list of chat up lines ever written. The kind that make you cringe so hard you feel physical pain.
I kept trying to redirect to normal conversation. “What do you do for fun?” “Have you traveled anywhere cool?” “Tell me about your dog!”
But he kept circling back to these horrible, cringeworthy pick up lines like he’d memorized a script and couldn’t deviate from it.
At one point, a couple at the next table actually turned to look at us. The woman gave me a sympathetic smile, like she felt sorry for me.
I checked my watch. We’d been there forty-five minutes. I could make an excuse and leave. Say I had a headache. Say my roommate needed me. Something.
The Moment Everything Changed
“Listen,” I finally said, putting down my coffee cup. “Can I be honest with you?”
His face fell. “Oh no. I messed this up, didn’t I?”
“The pickup lines… they’re just… they’re not really working.”
He covered his face with his hands. “I knew it. I knew I was being weird. I’m so sorry.”
“Why are you using them?” I asked gently.
He lowered his hands. His eyes looked genuinely sad. “Because I really liked talking to you online. And when you agreed to meet me, I panicked. I’m not smooth. I’m not naturally charming. I’m actually kind of awkward at first dates.”
“So you Googled pickup lines?”
“I read three different articles about worst pickup lines to avoid, and then somehow convinced myself that using them ironically would be funny.” He laughed bitterly. “I’m an idiot.”
I felt my irritation melting away. “You’re not an idiot.”
“I am though. Because the truth is…” He took a deep breath. “I don’t need a pickup line. The real thing I wanted to say is just… you seem amazing. Talking to you these past two weeks has been the best part of my days. You’re funny and smart and kind. And I was so nervous about meeting you that I completely forgot how to just be myself.”
He wasn’t using a line. He was being real.
“I’m sorry I wasted your time with all those terrible chat up lines,” he continued. “You deserve better than that. You deserve someone who’s confident enough to just tell you the truth.”
My heart did this weird flutter thing.
The Truth About Bad Pickup Lines
“Can I tell you something?” I said.
He nodded, looking miserable.
“Those pickup lines were awful. Genuinely some of the worst I’ve ever heard.”
“I know—”
“But,” I interrupted, “what you just said? That was perfect. That’s what I wanted to hear.”
His eyes widened. “Really?”
“Really. You don’t need dirty pickup lines or clever tricks. The reason I agreed to meet you wasn’t because I thought you’d be smooth. It’s because you were genuine in your messages. You asked real questions. You remembered things I said. You made me laugh without trying too hard.”
“So you’re not leaving?”
“No, I’m not leaving.” I smiled. “On one condition.”
“Anything.”
“No more pickup lines. Just be yourself. Tell me about your actual life. Your weird hobbies. Your embarrassing stories. The real stuff.”
He laughed—a real, relieved laugh. “I can do that. Although fair warning, my embarrassing stories are pretty terrible.”
“After those pickup lines, I can handle anything.”
What Happened Next
We stayed at that coffee shop for three more hours. Talked about everything. He told me about his job as a teacher. About his students who drove him crazy but made him laugh. About his rescue dog who ate his couch cushions. About his failed attempt to learn guitar.
No more pick up lines for guys material. No more trying to be someone he wasn’t. Just honest conversation.
When we finally left, the sun was setting. We walked to the parking lot slowly, neither of us wanting the date to end.
“Can I be honest about something?” he asked as we reached my car.
“Please do.”
“I actually prepared one more pickup line. But I’m not going to use it.”
“Now I’m curious.”
He shrugged. “It doesn’t matter. Lines don’t work. But you know what does work? Asking if you’d want to see me again. Like, a normal person would ask.”
I smiled. “I’d love to see you again.”
His whole face lit up. “Really? Even after all those cringy rizz lines?”
“Especially after those. Because they showed me something important.”
“What’s that?”
“That you were willing to look stupid just to try to impress me. That’s actually kind of sweet. Misguided, but sweet.”
He laughed. “My friends told me the same thing. They said I was overthinking everything.”
“Listen to your friends more.”
We stood there for a moment, and I could tell he wanted to kiss me but wasn’t sure if he should.
“You can kiss me,” I said. “No pickup line required.”
He did. And it was perfect.
Looking Back Now
That was three years ago. We’re engaged now. Getting married next summer.
At our engagement party, his best man told everyone about our disastrous first date. About how he’d spent hours researching funny pick up lines and dark pickup lines and every variation of terrible pickup lines he could find online.
“I thought I needed to be someone else to win her over,” he explained to our friends and family. “I thought being myself wasn’t enough.”
“But it was enough,” I added, squeezing his hand. “It was always enough.”
People ask me now what the secret to a good relationship is. I always think back to that coffee shop. To those awful, horrible, cringeworthy pick up lines that almost ended our date before it really started.
The secret isn’t about being smooth or saying the right things. It’s about being willing to be vulnerable. About admitting when you’re nervous. About being honest even when honesty makes you look foolish.
My fiancé didn’t win me over with his weird pick up lines or his attempts at being charming. He won me over by dropping the act and showing me the real person underneath.
The Real Lesson
If you’re reading this and you’re about to go on a first date, please learn from his mistakes. Don’t Google freaky pickup lines or dirty rizz lines or any of those horrible pickup lines you find online.
Those bad pick up lines? They don’t work. Not the clever ones. Not the funny ones. Not even the ones that seem like they should work.
What works is being yourself. What works is genuine interest in the other person. What works is asking questions and actually listening to the answers.
Save the terrible chat up lines for jokes with your friends. When you’re trying to connect with someone real, just be real yourself.
My fiancé tried seven different pickup lines on our first date. They were all awful. But his honesty? That eighth attempt where he dropped the act and spoke from his heart?
That one worked perfectly.
And three years later, I’m still glad he ran out of bad pickup lines and found his real voice.
Because that voice is the one I want to hear for the rest of my life.
Have you ever had a disastrous first date that turned into something beautiful? Did someone use terrible pickup lines on you? Share your story in the comments—I promise not to judge!
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