Pickup line fails
At some point in history, a group of men decided that smooth-talking their way into a woman’s DMs was an art form. Unfortunately, many of them were working with broken crayons. We’ve all seen it—the bold yet doomed attempt at flirtation that crashes and burns before it even leaves the runway. Maybe it’s the guy who thinks calling someone “kitten” is sexy. Or the one who believes a pun about melons is the key to everlasting romance. Either way, pickup line fails exist in an endless supply, and somehow, they just keep getting worse.
There’s a fine line between confidence and sheer delusion, and these examples bulldoze right past it. The moment a guy decides to use a recycled one-liner from the depths of the internet, you know you’re about to witness a disaster in real time. Some attempt to be poetic but end up sounding like they got their material from a fifth grader’s joke book. Others think “negging” is still a viable strategy, as if insulting someone is a shortcut to their heart. And then there are the truly unhinged attempts—lines so baffling they leave the recipient questioning not only the sender’s intentions but also the entire concept of human interaction.
You just scrolled through 25 of the worst attempts at digital romance, each one a masterpiece in its own uniquely awful way. From creepy wordplay to misguided confidence, these pickup line fails were a crash course in how not to flirt. You probably cringed, winced, and maybe even questioned whether some of these guys have ever spoken to another human being before. But hey, at least you got a good laugh—and maybe a renewed appreciation for normal conversation.
If you enjoyed watching these trainwrecks unfold, you’ll probably love exploring other meme collections featuring the worst dating fails, painfully awkward text exchanges, and clueless social media moments. Or, if you’re in the mood for more internet disasters, why not check out memes about relationship struggles, overconfident men failing spectacularly, or the absolute chaos of modern dating apps?
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Roy R., Chief Meme Curator
Roy founded Thunder Dungeon in 2012 and has since guided its growth into a 2.5 million‑strong community of meme enthusiasts. With over a decade of digital‑media experience and a nose for viral humor, Roy oversees content strategy, ensuring every post is both hilarious and high‑quality
