Retired Playboy Shares His Most Hilarious Pick-up Lines That Worked on Girls at the Bar Back in the Day

We weren’t just interested in the occasional phone number or fleeting fling. No, we were on a quest to perfect the ultimate arsenal of charm and wit. I mean, we called ourselves playboys, so charm and wit were the best weapons we could have.

Over the years, through trials and hilarious (sometimes inappropriate) errors, we gathered a collection of lines that ranged from cheeky to downright absurd.

Now, as a retired playboy, I feel it’s my duty to pass on the torch.

So, here, take the torch. These are some of the best lines that worked wonders back in the day.

1. The Magic Pen Trick

Ladies love a bit of magic, right?

Do you want to know the secret? Always carry a pen. Not just any pen, but one that works flawlessly. Spot the woman you want to talk to and approach with confidence.

“Here, let me show you something,” you say, grabbing a napkin.

With a flourish, draw a line across the napkin and hand it to her.

She’s going to look puzzled, trust me.

“What’s this?” she’ll ask.

Smile!

“A pickup line,” you smile.

Trust me, it’s gold.

2. Low Standards Proposal

A friend of mine, Tim, met his now-wife with this lovely gem of a line.

He walked to her group and confidently asked them a question.

“Who among you has low standards?”

It was so audacious that it worked.

“Me,” she said, approaching Tim with a smirk. “Show me what you’ve got.”

Sometimes, it’s all about the bold approach.

3. The Big Mistake

Once, I walked into a party and saw a gorgeous woman trying to open a bottle of wine.

Before I could plot my line, I ended up slurring my words to her.

“Hey there, want to make a big mistake?” I asked.

She laughed so hard that she had to put the bottle of wine down for fear of dropping it. We ended up talking all night.

Look, boldness can be charming, especially when delivered with a hint of self-deprecation.

4. The Classic Quarter Line

I was standing outside an Irish bar one night when a woman walked out smiling at the night sky.

“Hey, do you have a quarter?” I asked her.

She looked puzzled and shook her head, her eyebrow raised.

“Why?” she asked. “What do you need a quarter for?”

“Because I need to call my mom and tell her that I just met the woman I’m going to marry.”

Yeah, it’s cheesy. But it’s got heart.

5. Bedroom Sale

This one is cheeky, so proceed with caution.

For my 30th birthday, my friends threw me a big house party. Naturally, they invited random people, too.

As I was checking out what was happening at the pool, I saw someone step out of the pool in a gold bikini.

“There’s a big sale in my bedroom right now. Clothes are 100% off!”

Again, it’s cheeky. But it is a guaranteed ice-breaker.

6. The Raisin Question

I was in a local supermarket trying to get my life sorted out and get actual food into my fridge. Beer and takeout just weren’t cutting it anymore.

But there she was, a stunning woman restocking the shelves.

“Do you have any raisins?” I asked her.

“No, not on this aisle,” she said.

“Well then, how about a date?” I asked.

It’s playful and innocent enough to be endearing.

7. The Fake Marriage Proposal

I met a woman at a friend’s wedding. I was a groomsman, so I was holding a bouquet of flowers while the bridesmaids were doing a dance for the reception.

There, I saw a woman named Jennifer from my past. Or so I thought at the time.

“Oh, your name is Jennifer?” I said. “No kidding, that’s my wife’s name.”

She looked at me confused. So, I gave her the bouquet of flowers that were hidden behind my back.

“Well, we’re not actually married yet. In fact, we’ve only just met.”

Smooth, right? It’s all about the delivery.

8. Santa’s Wishlist

I was invited to be a friend’s plus-one to his office’s end-of-year function. It was heavy on the Christmas décor and there were easily about 200 people there.

I stood awkwardly at the edge of the party until someone approached the table of food next to me.

“Can I take a picture of you so I can show Santa what I want for Christmas?”

Trust me, seasonal charm never fails to get a smile.

9. The Flirtation Fail

As a self-labeled playboy, I had to stay in shape. So, I frequently went to the gym.

One day, I thought I’d try my luck.

“If I said you had a nice body, would you hold it against me?” I asked someone who was working out next to me.

It’s a classic for a reason but use it sparingly. Especially because I had a dumbbell land on my foot.

10. The Lost Number

One night when I was at my favorite bar, I saw a woman sitting by herself and sipping on a gin and tonic. She seemed bored and annoyed.

That was my cue.

“I seem to have lost my phone number,” I said. “Can I borrow yours?”

This one is simple and direct and perfect for a quick laugh.

11. The Honest Approach

I was at a concert one evening, and it was loud and lively and the perfect place to try a different line.

Standing at the pop-up drink stand, I was next to a woman who was trying to get her order in.

“I know what you’re thinking, and you’re wrong. You do stand a chance with me.”

She laughed loudly and nodded.

“Get me a drink and we’ll see,” she said.

12. Tech Talk

After my laptop took a nosedive into my pool (don’t ask), I had to have it replaced. So, I found myself at a tech store.

“Are you the bottom of my old laptop? Because you’re hot,” I said to the salesperson helping me.

She sniggered and walked away. Naturally, she tried to sell me the most expensive laptop in the store.

13. The Spoon Line

This one is cute and funny.

I was at a café one evening. As I sat at the counter waiting for my order, the waitress gave me a little smile.

“Do you have a fork?” I asked.

She shook her head.

“How about a knife?”

Again, she shook her head.

“Well, do you want to spoon with me?”

She burst into laughter until the kitchen called her with my order.

14. Drawing Attention

I took my nephew to a soccer game once. And while he was engrossed in the game, I was thinking of a line to use on the person sitting next to me.

“No pen, no paper, but you still draw my attention,” I said.

She beamed and then laughed.

While my nephew pulled my arm.

“I’d like a pretzel, please,” he said.

15. Dog Park

My German Shepherd used to get really cranky when he didn’t get to go on walks. So, I took him to the dog park down the road.

There was a woman with her husky, playing fetch.

“You must definitely be a dog person because you look fetching,” I said.

She threw the dog’s ball straight at me and laughed.

These lines are the results of years of research and practice. Use them wisely, with a smile and a bit of charm, and you might find yourself in some interesting conversations.

And remember, don’t be inappropriate! The best pick-up lines are the ones that make people laugh and feel good.

Good luck! Let me know how it goes!

If you enjoyed this compilation, here’s another one for you |

Golden Years Humor: 7 Jokes about Grandmas and Grandpas

Let’s face it, grandparents hold a special place in our hearts, with their wisdom, love, and sometimes, their hilariously quirky ways. They remind us that age is nothing but a number and laughter is the best medicine (it’s free, too!).

Here are some delightful stories that highlight the humor and love that comes with living a long and interesting life. Good luck getting through this without laughing!

1. Dear Old George’s Annual Check-Up

Without fail, George went for his annual check-up every year. He prided himself on staying fit and healthy by going on walks in the neighborhood, though age had taken its toll on his eyesight.

After his check-up, George sat and chattered with his doctor, proudly telling Dr. Stephens about his latest discovery.

“Doc, I’m blessed,” he said. “God knows my eyesight is going, so he puts on the light when I pee, and turns it off when I’m done!”

The doctor chuckled, but a nagging curiosity led him to call George’s wife later that day.

“Maria,” he said. “Your husband’s test results are just fine. But he said something strange! He claims that God turns the lights on and off for him when he uses the bathroom at night.”

George’s wife laughed out loud.

“That old fool! He’s been peeing in the refrigerator again! I thought it was the dog!”

2. The Mischievous Grandmas on a Bench

Three mischievous grandmas were sitting on a bench outside of their nursing home, laughing their heads off like giggling girls.

“Now, now, ladies,” a nurse said, walking past them. “You need to get your sunshine time before tea. And behave!”

Her words only set them off again. Soon, they spotted an old man walking by and decided to have a bit of fun with him.

“We bet we can tell exactly how old you are,” one of the grandmas yelled out at him.

The old man scoffed.

“There’s no way that you can guess it, you three old fools.”

“Sure we can!” another grandma insisted. “Just drop your pants and we can tell your exact age!”

“What?” he exclaimed.