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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.

More info: Instagram

#1

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

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UKDeek
Community Member
1 year ago (edited)

Brilliant - The only way to deal with such an absolute nugget like that...

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    #2

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

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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    Yo gaby this is St Peter....

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    #3

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

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    Ellinor she/they/elle
    Community Member
    1 year ago

    Oh, if only you could slap people through a screen... One can only hope I guess !

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    #4

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

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    Ellinor she/they/elle
    Community Member
    1 year ago

    Well at least he announce his red flags right away, I'll give him that...

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    #5

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

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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    Ha ha, I like lefty!

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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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    Niki
    Community Member
    1 year ago

    Today I learned women can't be Italian.

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    HAHAHAHAHA

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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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    Deborah B
    Community Member
    1 year ago

    Because men were trying to sneak looks at our arses?

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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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    Jaya
    Community Member
    1 year ago

    It's his mindset/behavior that is the problem, not the name. People don't choose their name (well, not most people anyway), no need to shame people over that.

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    *Look around while embarrassed* Can someone come save me please ? *she thinks while smiling awkwardly to the strange man*

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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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    Riaan van der Walt
    Community Member
    1 year ago

    I feel sad for the world.

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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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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    It's what your grandma would have wanted.

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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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    HistoryNerd
    Community Member
    1 year ago

    Negging, how original 🙄

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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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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    Hi this is Ian's nigerian uncle who happens to be a general.

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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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    Riley Quinn
    Community Member
    1 year ago

    Not understanding basic social decorum is beyond weird. You don't bring up your crazy thoughts until the 3rd date.

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    Never miss a story that brings joy to the world. Add us on Google

    #16

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

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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    Pity it spends all its time bashing the Bishop. Just saying.

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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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    Ellinor she/they/elle
    Community Member
    1 year ago (edited)

    Nope ! He's going to be one of those "cinema lover" that only gives credit to obscure Siberian movies with Russian subtitles in black and white made in the 18th century.

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    And now ladies and gentlemen, if you look to your right you can see the very rare specie called "Alpha Males". No flashes with the pictures please, they are VERY sensitive.

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    #19

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

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    Ellinor she/they/elle
    Community Member
    1 year ago

    And it probably never will.

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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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    ToothlessNightwing
    Community Member
    1 year ago

    🤮

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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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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    I want u to have my babies

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    #22

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

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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    Yes feminism is about providing spank bank material for immature men. This is what Emily Pankhurst campaigned for!

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    Is he talking to himself ?

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    """I""" don't use pronouns.

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    #25

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

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    Cheese
    Community Member
    1 year ago (edited)

    How does he pick which letters to capitalize?

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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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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    Someone's inflated ego has been successfully pricked.

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    #27

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

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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    Perhaps he should talk to a therapist.

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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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    Ellinor she/they/elle
    Community Member
    1 year ago (edited)

    As a fallopian tube owner, that's really really not s3xy.

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    Yeah, because no one can be smart if they don't read ancient books every second of the day, that's a well known fact ! /s

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    He must be a geologist.

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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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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    Oh no! A woman replied! How do I respond? Red alert! Battle stations! Let's try not to panic!

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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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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    First you need to meet a girl.

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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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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    This is almost poetry.

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    Yeah, sexism is so sad (by the way I'm 6'2, I go to the gym everyday and get paid 12 millons a month ladies 😉)

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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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    Dolevaal
    Community Member
    1 year ago

    Sure, bc emotional pressure always work 🙄

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    I hate this guy.

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    HOW ??? Like genuinely HOW do you make that connection ?

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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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    UMUMO
    Community Member
    1 year ago

    Not the demons thing AGAIN

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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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    Mreoww
    Community Member
    1 year ago (edited)

    Edit: r/im14andthisisdeep.

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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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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    That is.... One way to look at it. Definitely the wrong way to look at it though.

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    #41

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

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    StarCrossedFriday
    Community Member
    1 year ago

    Maybe don’t send messages in the middle of the night and draw conclusions from a lack of reply within an hour?

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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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    Dolevaal
    Community Member
    1 year ago

    Atleast he saw that was inappropriate and rude. A (small) step forward.

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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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    Dolevaal
    Community Member
    1 year ago

    Good point. Why would you think a completely stranger would have to make time for you? You dont even know each other.

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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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    Jaya
    Community Member
    1 year ago

    I think that's kind of a cute opening line. Assuming it's on a dating site.

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    #46

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

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    HolyGuacamole🥑🥑
    Community Member
    1 year ago

    If we were to make a list of things that are a complete and utter turnoff, anything to do with crypto would be very near the top.

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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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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    Why Mr. Darcy! You are charming beyond compare!

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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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    HistoryNerd
    Community Member
    1 year ago

    I've though about it and I'd rather have COVID

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    #49

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

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    Ellinor she/they/elle
    Community Member
    1 year ago

    Well, well, well... If those aren't the consequences of your own actions ?

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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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    Deborah B
    Community Member
    1 year ago

    Really. You're going to lead with "I'm h***y" and then complain that women are assuming you are looking for a hook up? She clocked you on word four.

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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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    Jaya
    Community Member
    1 year ago

    I don't get the logic at all, but I can't stop laughing at this one.

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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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    nottheactualphoto
    Community Member
    1 year ago

    Please, proceed.

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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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    Dolevaal
    Community Member
    1 year ago (edited)

    But you are not nice.

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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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    Ellinor she/they/elle
    Community Member
    1 year ago (edited)

    Well at least he kinda meant well ?

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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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    Dolevaal
    Community Member
    1 year ago

    Goodbye.

    #56

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

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    Power puff scientist
    Community Member
    1 year ago

    Why ask random strangers on Internet for this. just visit Google or a pornsite and you could see plenty. Corey could reply here : you would know.

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    Yeah, same...

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    #58

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

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    Nathaniel He/Him Cis-Het
    Community Member
    Premium
    1 year ago

    hey xx

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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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    Annik Perrot
    Community Member
    1 year ago

    "Pipe" in French means à blôw-job. I guess that's not the meaning here?

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    EW.

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    Well that makes both of you.

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    *block*

    #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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    Ellinor she/they/elle
    Community Member
    1 year ago

    Now is the perfect time for finding his wife and sending her that screenshot.

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    #65

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

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    Ellinor she/they/elle
    Community Member
    1 year ago

    Call the police.

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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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    Dolevaal
    Community Member
    1 year ago

    Appearently not.

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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 d***h.

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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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    Jaya
    Community Member
    1 year ago

    This one is quite funny. It's kinda like "I love true crime" and then realizing that you technically said you like people getting m******d and stuff, instead of liking podcasts/tv shows about it.

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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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    Boredest Panda
    Community Member
    1 year ago

    You could’ve stopped an insulting the lips. Then everyone would’ve walked away only feeling mildly uncomfortable. But the dog? He should make sure to lock all of his doors tonight.

    #71

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

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    StarCrossedFriday
    Community Member
    1 year ago

    Was this an opening message? What possible response could they have expected?

    #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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    Ellinor she/they/elle
    Community Member
    1 year ago

    I'm stealing that insult.

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    And then he say something very popular like Queen or The Beatles.

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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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    Ellinor she/they/elle
    Community Member
    1 year ago

    Oh we know, we know.

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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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    HistoryNerd
    Community Member
    1 year ago

    Unpopular opinion, but this is kind of funny

    #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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    Jaya
    Community Member
    1 year ago

    Telling a person it's weird that you like them because they're not conventionally attractive... yeah, that's really how you win someone's heart 🙄

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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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    Berblogs
    Community Member
    1 year ago

    The sent from my iPhone really ties the whole thing together

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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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    and_a_touch_of_the_’tism
    Community Member
    1 year ago

    Meh, I can respect that. They’re being honest.