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21 Awesome Stories About First Dates from Masters of Flirting

Inspiration

21 Awesome Stories About First Dates from Masters of Flirting



A great and beautiful feeling can begin with a funny and awkward moment. But that’s even better: you’ll have something to remember and laugh about together.

found some great stories of totally unromantic first meetings, and we would like to share them with you.

  • This morning, I bought myself a cup of coffee, looked at it after a few steps, and saw “Call me” written with chocolate crumbs in the foam. I smiled but couldn’t understand how to call until I drank all the coffee. There was his number written on the bottom of the cup. This was the sweetest pickup attempt in my whole life.
  • Going down in an elevator with the taxi to the airport already waiting outside, I suddenly realize I forgot to put insoles into my boots. I go back up to the 20th floor, too slowly, thinking I’d rush to my apartment for the insoles and back before the elevator’s gone. Then I see a girl on my floor. I ask her to wait for me for just a couple of seconds. She gives me a coquettish smile and nods. I run for the insoles and hear the elevator doors closing. Thinking why she would be so mean, I come back, and there she is waiting for me without the elevator.
  • There she goes along the street — pretty, stylish. And I just went numb with fear, but I had to talk to her. I approach her, grinning like an idiot, and mumble, “Excuse me. What’s the time, please?“
    She produces her phone and tells me. I needed all this only to start a conversation, and the main question was ahead. Finally, I found my guts and asked, ”Do you believe in God?”
  • I was going home by bus and listening to the radio. They read the horoscope, and when I realized I wouldn’t hear about my sign, I decided to go an extra stop. When I got off the bus, a guy came down with me and asked, “Excuse me, are you also an Aquarius living at the previous stop?”

  • A story told by my teacher. He was going home from the university and saw a couple of girls, his then groupmates. He decided to impress them: he stealthily ran into a house that was closed for renovation, climbed onto a ledge on the first floor, and jumped from about 5 feet onto the pavement right before the girls, but hitched on a metal rod… As a result, two fractured arms and a concussion. On the bright side, the girls took him in and called an ambulance and then visited him in the hospital. Now, he’s been married to one of them for 25 years.
  • I love my dad. When I was a kid, he came home drunk, produced a kitten from a pocket, and said, “Sonny, this is Bonifacius, and he’s all yours!“ My mom was angry at first but then settled. After a couple of years, he did the same thing with a dog: ”Sonny, this is Rex, and he’s all yours!” Mom was angry again and then okay again. Some years later, Dad came home with his colleague and his daughter and said, “Sonny, this is Sveta. Well, you get the idea.” We’ve been married for 3 years now

  • A small cafe. I’m drinking my coffee. At the bar is a pretty blonde girl, Lera. A small line of customers, everyone trying to impress her with insipid jokes. Then Andrew goes in, a former military officer. He apologizes, goes straight to the bar, produces a bill, and says, “Silver!“ Lera looks him up and down and gives him a pack of Parliament, saying, ”That’s a man: concise and to the point.“ Andrew thinks a bit, looks back at Lera, and says, “At eight!” To which she replies, without thinking, ”At nine!” To cut it short, Andrew was late but happy the next morning.
  • Once I went to a museum to kill some time. It was pretty boring, and I began taking selfies. A really handsome guard approached me and said, “Excuse me, miss, but please don’t photograph the art objects.“ I apologized and explained that I was only taking a selfie, to which he replied, ”I know,” and winked at me.
  • I was running after my bus, tripped, and fell over into a puddle. A man came along, helped me up, and asked, “You think you’ll make it faster by swimming?” That’s how we met.

  • When I came to my new school in the 9th grade, my future wife was already there. Before September 1, she saw a new last name on the list and laughed at it, saying it was weird and making jokes with her friends. So naive.
  • I once flirted with a bartender, a cute blonde girl. We were talking, and she asked me if I had a girlfriend. I said, “No, but I know what she’d look like if I had one. Wanna see a picture?“ She said, ”Yeah, sure.” Then I set my phone to the frontal camera and gave it to her. When she saw herself, she laughed and blushed.
  • A guy I liked very much asked me out to a restaurant. I was a student then with no money and only naked pasta for every meal for two years. I thought I’d go and order a coffee if I had to pay for myself. When we got our menus, he said, “You hungry? Order something. It’s on me.” I leaf through the menu, smiling. And then a drop of my saliva falls on the table.

  • A friend of mine once lost a wager. He had to go to some tall building at night and shout “Greg!“ for 40 minutes. So he comes to the house at 2 a.m. and starts shouting. Loudly. In about 20 minutes, a light goes on at the third floor, a window opens, and a bowl of cold water falls down on our guy. A girl looks out the window then and says, ”I thought you’d grown thirsty, shouting and all, so here’s some water.” The guy smiled and asked for some warmer water lest he should catch a cold. In a couple of minutes, another bowl of warmer water goes down. To cut it short, they started talking eventually. It’s been 5 years now, they’re expecting a second kid, and every year on the day of their meeting they go to a waterpark.
  • When I studied in college, I worked as a bartender. Once I saw a guy approaching a girl and saying, “Hi, I’m Ben, and I’ll buy you cocktails until I’m handsome in your eyes.“ She smiled, then laughed. He asked her what she would like to drink. She looked at him (and he was really handsome), turned to me, and said, ”Water, please.” I’m sure they spent a great night.

  • As a student, I worked at a local mall where I knew a beautiful and single shop assistant. My advances were very weird. I would change the position of every mannequin in her store each night: a hand here, a head there, make them look at each other, etc. I’d wait for her to understand it was me trying to get her attention. Then, one day I didn’t see her at work. Rumor had it she’d quit the job and told her boss the mannequins were alive. The boss got angry and made her go. If you read this, I’m sorry. I just wanted to get to know you.
  • I was sitting at a cafe, drinking juice, and looking at a handsome guy. When our eyes met, I choked, and juice flowed out of my nose. The guy laughed, came to my table, and said, “Wow, you’re good at attracting men!”
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