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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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#1

Text message screenshot showing a cringy man insisting on correcting and mentally preparing a woman.

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    #2

    Cringy men hitting on women with dramatic and desperate messages in late-night text conversations.

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    #3

    Screenshot of a cringy conversation showing men hitting on women with awkward and controlling messages.

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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.

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    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?

    #4

    Text message exchange showing a cringy man hitting on a woman with insecure and lowkey girl comments.

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    #5

    Screenshot of a cringy conversation where a man misunderstands questions while hitting on a woman.

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    #6

    Screenshot of a cringy man expressing frustration about females listening to Radiohead and being social rejects.

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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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    #7

    Screenshot of cringy men hitting on women with awkward and inappropriate messages in a text conversation.

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    #8

    Screenshot of cringy men hitting on women with misleading and outdated comments on a dating app conversation.

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    #9

    Screenshot of cringy men hitting on women with awkward and polite but ineffective pickup messages in a chat conversation.

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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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    #10

    Screenshot of a cringy message from a man nervously asking a woman out on a date, showing awkward flirting.

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    #11

    Screenshot of a cringy message from a man hitting on a woman with awkward and pushy language shared by women online.

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    #12

    Screenshot of a cringy text message from a man showing awkward persistence and sympathy in online conversations.

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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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    #13

    Screenshot of a cringy man awkwardly hitting on a woman with confusing and backhanded compliments in a text chat.

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    #14

    Screenshot of a cringy chat message showing emotional text from a man hitting on a woman, highlighting awkward interactions.

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    #15

    Text message exchange showing cringy men hitting on women with awkward and humorous responses in a dark chat interface.

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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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    #16

    Tattooed man’s dating profile with a creepy message, part of cringy men hitting on women screenshots collection.

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    #17

    Text message conversation showing a man awkwardly asking about favorite Wes Anderson films, part of cringy men hitting on women.

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    #18

    Screenshot of a cringy text message from a man hitting on a woman with awkward emotional comments.

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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.

    #19

    Text message conversation showing cringy men hitting on women with awkward and rejected pickup lines.

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    #20

    Screenshot of a cringy man hitting on a woman, sharing messages about beauty, mental health, and blocking her.

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    #21

    Screenshot of a cringy message from a man hitting on a woman, showing awkward and contradictory text replies.

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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.

    #22

    Cringy men sending messages denying misogyny and demanding nudes, shared by women in screenshots.

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    #23

    Cringy men hitting on women with awkward and inappropriate messages in a screenshot of a text conversation.

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    #24

    Text message exchange showing cringy men hitting on women with awkward comments about pronouns and music preferences.

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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.

    #25

    Screenshot of cringy men hitting on women with awkward and toxic messages in a late-night texting conversation.

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    #26

    Screenshot of a cringy men hitting on women message with disrespectful and defensive tone in a text conversation.

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    #27

    Text message screenshot showing cringy men hitting on women with awkward and strange chat messages.

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    #28

    Text message exchange showing a cringy man awkwardly hitting on a woman with a confusing comment about the fallopian tube.

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    #29

    Screenshot of a cringy message from a man hitting on a woman with a sarcastic response about reading the Odyssey.

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    #30

    Screenshot of cringy men hitting on women with repetitive messages about rocking their world over several months.

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    #31

    Screenshot of a cringy man hitting on a woman with mixed messages in a text conversation.

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    #32

    Text message exchange showing a woman discussing rare interests, part of cringy men hitting on women screenshots.

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    #33

    Screenshot of a cringy message from a man hitting on a goth girl, shared by women in awkward flirting stories.

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    #34

    Muscular man taking a mirror selfie with a humorous caption about women facing oppression in the workforce and cringy men hitting on them.

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    #35

    Screenshot of a cringy message from a man hitting on a woman with desperate and awkward lines.

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    #36

    Screenshot of a cringy message from a man discussing feminism and gender roles in a controversial tone.

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    #37

    Screenshot of a debate post saying astrology is just racism for girls shared by women in cringy men hitting on them thread

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    #38

    Screenshot of a cringy message from a man apologizing after hitting on a woman, shared in a collection of awkward texts.

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    #39

    Screenshot of a cringy message from a man expressing emotional feelings, shared in women’s cringe hits collection.

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    #40

    Screenshot of a cringy text conversation showing a man’s awkward response about sharing an std, highlighting cringe men hitting on women.

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    #41

    Screenshot of cringy men hitting on women with awkward messages shared on Messenger conversations.

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    #42

    Screenshot of a cringy message from a man hitting on a woman, part of women sharing cringy men hitting on them.

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    #43

    Screenshot of a cringy text message from a man apologizing, shared by women highlighting awkward online interactions.

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    #44

    Cringy men hitting on women with awkward breakup texts and humorous responses in screenshots shared by women online.

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    #45

    Screenshot of a cringy men hitting on women direct message with a dog emoji and awkward compliment.

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    #46

    Cringy men hitting on women with awkward crypto-themed pickup lines in text message screenshots.

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    #47

    Screenshot of a cringy text conversation with a man awkwardly hitting on a woman using unexpected and awkward language.

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    #48

    Screenshot of a cringy text message from a man hitting on a woman during late night, shared by women online.

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    #49

    Screenshot of cringy men hitting on women with awkward and inappropriate messages shared online.

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    #50

    Screenshot of a cringy man hitting on a woman, showing awkward messages from a dating app conversation.

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    #51

    Screenshot of a cringy man’s direct message using a Kafka quote to manipulate bisexual women in awkward flirting attempt.

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    #52

    Screenshot of cringy men hitting on women with awkward and inappropriate text messages in a chat conversation.

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    #53

    Screenshot of a cringy men hitting on women conversation showing awkward and defensive messages in a dating app chat.

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    #54

    Text message conversation showing cringy men hitting on women with confusing and awkward comments about gender terminology.

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    #55

    Screenshot of a cringy text message from a man hitting on a woman with emotional manipulation attempts

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    #56

    Screenshot of a cringy man hitting on a woman with awkward messages in a chat conversation.

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    #57

    Screenshot of a cringy text conversation showing awkward messages from a man hitting on a woman.

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    #58

    Screenshot of cringy men repeatedly texting hey with kisses and awkward questions in a conversation.

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    #59

    Text message conversation screenshot showing cringy men hitting on women with awkward pickup lines and responses.

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    #60

    Screenshot of a cringy man’s dating profile message showcasing awkward attempts at flattering women online.

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    #61

    Screenshot of a cringy message from a man on a dating app, shared by women highlighting awkward conversations.

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    #62

    Screenshot of a cringy message from a man hitting on a woman, questioning her eyeliner and declaring love awkwardly.

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    #63

    Screenshot of a cringy message from a man hitting on a woman late at night, illustrating awkward online interactions.

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    #64

    Screenshot of a cringy message from a man hitting on a woman at Trader Joe’s shared by women online

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    #65

    Screenshot of a cringy conversation with men hitting on women, showcasing awkward and unwanted messages.

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    #66

    Screenshot of a cringy man messaging about good taste in music, shared by women who experienced awkward online interactions.

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    #67

    Screenshot of cringy men hitting on women with repeated text messages asking about watching Borat tonight.

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    #68

    Screenshot of a cringy text message exchange showing awkward flirting from a man after sad news about Prince Phil's death.

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    #69

    Screenshot of cringy men hitting on women with awkward historical references and awkward apologies in messages.

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    #70

    Screenshot of a cringy man messaging an insult to a woman with a photo of a dog in a social media reply.

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    #71

    Screenshot of a cringy message from a man hitting on a woman, showcasing awkward and unsolicited flirting.

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    #72

    Screenshot of a cringy message from a man on a dating app, shared by women showcasing cringy men hitting on them.

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    #73

    Text message screenshot showing a cringy conversation with men hitting on women, illustrating awkward online flirting.

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    #74

    Screenshot of a cringy message from a man, part of women sharing cringy men hitting on them collection.

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    #75

    Screenshot of a cringy online conversation showing a man awkwardly hitting on a woman discussing what it means to be normal.

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    #76

    Text message screenshot showing a cringy man sending a Spotify link to the song Mr. Brightside, hitting on a woman.

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    #77

    Screenshot of a cringy man hitting on a woman with an awkward and over-the-top message on social media.

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    #78

    Screenshot of a woman’s blunt reply to cringy men hitting on her, expressing no interest and setting clear boundaries.

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    #79

    Screenshot of cringy men hitting on women with awkward and blunt messages about hookups and honesty.

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