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Heartstrings and Headshakes: Exploring the Memorable Pickup Lines That Left Women Spellbound or Speechless

In the unpredictable world of dating and romantic pursuits, you would expect a cringe-worthy, eye-rolling pickup line not to produce positive results. However, love has a way of defying expectations. Sometimes, against all odds, the worst pick-up lines have managed to work their magic, leaving both the sender and recipient pleasantly surprised. 

Pizza Rolls

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Image credits: Depositphotos DmitryPoch.

One user shared, “My now husband messaged me on a dating app about pizza rolls. I can’t even remember the quote. I just know that it worked, lol.”

Dinner & Dishes

Homemade Food woman cooking at the stove in a red apron
Image credits: Depositphotos Ariwasabi.

This Redditor said, “While I was in college, I dm’d my crush, “I’ll cook us dinner, and you wash the dishes.” I don’t know how, but it worked.” 


The “Pat Down” two men standing outside talking
Image credits: Depositphotos DGLimages.

This user recalled, “I thought he was gay, we went to a party where I found out he wasn’t, and I told him what I had thought, to which he replied: “Let’s go outside so I can show you how not gay I am.”

Gut Feelings

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Image credits: Depositphotos helenaak14.

One Redditor said, “The first message to my girlfriend on Tinder was, “dang girl are you my appendix? Cuz I have this gut feeling I need to take you out” Just stupid enough to work. We’ll be together for 4 years this November!”


Woman and Man head to head smiling
Image credit: Depositphotos gstockstudio.

A user shared, “A random guy at a BBQ… The group is talking about going on an activity the next weekend. “Well, I’m not going unless She’s going” *Nods in my direction* What kind of lame sh****t is this? I didn’t even remember this fool’s name. 12 years later. Married.”

Sharing Interests

man looking grossed out
Image credit: Depositphotos AntonLozovoy.

This Redditor stated, “I was at a house party and, for some stupid reason, said to this hot girl “There’s no one out on the deck if you’re interested.” I guess she was interested. Been married 32 years.”


Woman looking surprised, wearing a green shirt
Image credit: Depositphotos DmitryPoch.

This user said, “My boyfriend of six years’ opening line on Tinder was, “Did you hear about the cheese factory explosion in France?” I said no…” All that was left was de Brie.” All it took was cheesy stupidity!”

Same Name

Open-mindedness man showing a thoughtful face
Image credits: Depositphotos Milkos.

A Redditor shared, “My girlfriend and I have the same name. My first message to her was saying how I told my mate (who was dating a girl who shared his name) that I could never do that at all and that it’s just a weird thing to do etc. And ended the message with, “So anyway, I’m Sam. Nice to meet you, Sam.”

A New Fetish

man standing with his hand on his head looking annoying
Image credits: Depositphotos antianti.

A top-liked comment said, “She had a photo on OkCupid of her doing a cheesy pose sticking her a*** out on a Segway. I said, “I think I just developed a Segway fetish.” Five years in July.”

Great Pick-Up Limes

Sense of humor couple laughing together and hugging
Image credits: Depositphotos

A user hilariously said, “Wrote my number on a lime to give her, told her it was my “best pick-up Lime” and she loved it.”


couple on a date
Image credits: Depositphotos monkeyimages.

This Redditor said, “One of my girlfriends had a guy walk up to her in a busy restaurant and straight up said, “You’re the most beautiful woman in this restaurant.” She said it was very sincere. They’re now married with a few kids!”

Minimal Time

Happy couple laughing in bed
Image credits: Depositphotos HayDmitry.

A user added, “In 2012, I told her, “Hey girl, if you ever come visit me, I’ll show you the most disappointing 3 minutes of your life. My number is—”. Coming up on 6 years of marriage.”

Going That Way

Flirting man and woman sitting and smiling holding hands
Image credits: Depositphotos nenetus.

This Redditor recalled, “A man from a Single Parent Support Group I went to saw me sitting at the bus stop waiting to go home. He did an illegal U-Turn, cut through part of a parking lot and through a gas station parking lot to pretend to be…” going in my direction..would I like a lift?”. We celebrated our 27th wedding anniversary in Thailand this past October.”

Corny Puns

Man and Woman Kissing wearing a suite and black dress
Image credit: Depositphotos VitalikRadko.

A user added, “I was closing down the cash office at work with the other manager, and out of nowhere, he says, “Hey, you wanna screw?” I turn around in horror, and he’s holding up an actual wood screw he found on the floor. I laughed but made it clear I had a boyfriend. A couple of months later, I was single and was passing by him in receiving, and he said, “If you don’t want a screw, how bout a snuggle?” while he was a bottle of Snuggle fabric softener. I said yes, it’s been 10 years together, married for almost 4.”

Mental Maps

woman thinking and looking to the side
Image credits: Depositphotos vitalikradko.

This user said, “My (eventual) husband tried to impress me by telling me he had a mental map of every Taco Bell in the city. I looked him dead in the eye and said, “Marry me.” 5 years later, we had Taco Bell catering at the wedding.”

A Reason To Talk

Chain Messages man texting and looking at his phone
Image credits: Depositphotos AndrewLozovyi.

One Redditor shared, My boyfriend messaged me in November 2020 via Facebook, “Happy birthday” My birthday is in May. He followed it with, “Oh well, now I have an excuse to talk to you.”

Multiple Languages

Happy couple hugging and laughing
Image credit: Depositphotos VeronikaGorBO.

This user stated, “Drunk on a balcony with some foreign students in college. One of them says, “I’m fluent in English, Russian, French, and Tajik. That means I’ve got a talented tongue”. How could I not find out after that?”

Try Again

Woman looking disgusted and pointing away
Image credit: Depositphotos khosrork.

A Redditor recalled, “I bent a bottle cap backward, put it on my nose, walked up to her, and asked, “Did you throw this at me?”. She waved me away and said to try again. Later that night, I returned, handed her an ice cube, and told her to throw it on the ground. She did so, and as the ice shattered, I said, “Hi, now that the ice is broken, I am [name]. Happily married for 11 years.”


Giving A Compliment happy couple smiling at each other
Image credits: Depositphotos ridofranz.

This user said, “My now husband hit me in the Twitter DM’s with “Do you have a twin?” My response was ummm, no? Why? To which he responded, “Then you must be the prettiest girl in the world.” I’m unsure how it worked, but we are 10 years later with 2 kids.

Circle Of Life

happy couple woman on mans back
Image credits: Depositphotos

Finally, a Redditor said, “His line was, “So, do we get married now?” I thought it was hilarious because I just got a divorce at the time.”

This Reddit thread on the worst pickup lines that made Redditors cave is a hilarious showcase of cringe-worthy dating encounters. It highlights the amusing and often absurd attempts at wooing that people have experienced. These stories serve as a reminder that genuine connection and humor are crucial when it comes to making a positive impression. Let’s take these entertaining anecdotes as a lesson to approach dating with authenticity and wit.

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Man and Woman Kissing wearing a suite and black dress
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