Sometimes, if you want to date someone, you’ve got to “shoot your shot,” as the saying goes. However, the distance and lack of accountability of things like text messages and DMs mean that some of the most unhinged folks out there are willing to just try anything, no matter how dumb.
We’ve gathered screenshots of some of the worst, cringiest and most clueless attempts at hitting on women some men have ever attempted. So get comfortable as you scroll through, upvote the most horrendous examples and be sure to share your own thoughts and stories in the comments down below.
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There's a very specific kind of interaction that a great many women are all too familiar with: a guy approaches, flirts, and when she sends out signals of disinterest, either overt or subtle, he just flat-out refuses to notice. Instead of gracefully stepping back, he keeps pushing on, piling her up with groan-inducing remarks, unasked-for compliments, or persistence that quickly glides from mildly annoying to full-on awkward.
The result is usually cringe-worthy, both for the woman who is rejected and for any onlookers to the embarrassment. So why do some men so completely misunderstand rejection, and why does it look so painfully awkward?
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Social conditioning is part of the reason. Men have been trained for decades that persistence is a good thing when it comes to charming women. Movies, TV shows, and even "how to date" books have a tendency to reinforce the idea that "if you stick it out long enough, she'll eventually agree." This myth makes some men believe that a woman's hesitation is just a challenge to be overcome, rather than a clear boundary to be respected.
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A second reason is ego. Rejection is painful, and to some men, it is painful like a blow to their ego. Instead of taking "no" for an answer, they try to save face by doubling back, cracking jokes, or playing dumb about the signals. The result, ironically, makes them seem even more desperate and cringeworthy. What could have been a moment of maturity, taking the lack of interest and moving on, becomes an act that screams insecurity.
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There's also the issue of reading between the lines. Some men literally struggle with reading between the lines, either because of poor social intuition or just desire masquerading as obstacles. If a woman is polite but direct, they'll misinterpret her being nice as a sign that she wants them to continue approaching rather than a signal that they need to back off. This miscommunication creates a dynamic where one believes they're being kind and the other thinks that it's an invite to continue approaching.
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The cringe factor is the product of this disconnect between what he tries to do and what actually occurs. When a man ignores obvious cues, his advances are no longer playful but awkward. The flattery is insincere, the jokes fall flat, and the assertiveness seems arrogant. The irony of the moment, for a bystander, is the way painfully clueless he seems, but for the woman, it's never funny. It's exhausting, infuriating, and sometimes even threatening.
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What is worse is that this type of behavior underestimates women altogether. It assumes they're being games or that their "no" isn't a real one. It removes their agency and treats them like puzzles to be solved rather than human beings who are very capable of knowing, and expressing, what they want. That lack of respect isn't just cringeworthy, it's disrespectful.
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The truth is that rejection is just a part of life, and the most attractive response is to accept it like a pro. A gentleman who takes a clue, gives a classy smile, and walks out makes a much better impression than a dude who clings for dear life to the instant in a desperate bid for validation. Ironically, confidence is demonstrated not by holding out in the face of rejection, but by the ability to take it in stride.
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In the end, men who are unable to take a hint are cringeworthy for the simple fact that they bring attention to a lack of self-awareness, respect, and confidence all at once. Not being able to let go isn't charming, it's being clingy. And while they may think persistence is complimentary, what women most want is someone who understands when to back down, honor boundaries, and move along without it getting awkward.
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