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Approaching someone to flirt can be stressful, it takes some social skills, suave and smoothness. This is perhaps why some folks prefer to text. However, this extra “comfort” comes at the cost of the least appealing people shooting their shot.

Some folks share screenshots of the worst, most embarrassing and cringy texts they’ve gotten from men in some misguided attempt at flirting. So get comfortable as you scroll through, upvote the worst examples and be sure to share your own thoughts and experiences in the comments below.

#1

I Thought That Was Your Thumb

Text message exchange with a humorous response, illustrating challenges in men approaching women.

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Boredest Panda
Community Member
2 days ago (edited) DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I mean people who send pictures like that to people probably have longer thumbs than d***s

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    #3

    NGVC: "Not Interested In Me? But I'm A Nice Guy! Must Be Racism"

    Chat conversation about men approaching women, discussing rejection and misunderstandings.

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    Boredest Panda
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    I love how people say “I’m a pretty nice guy” after saying something pretty not-nice.

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    Unfortunately, there have been guys making unwanted and, frankly, horrible advances for, probably, much of human history. Over a hundred years ago, in Washington D.C. Alice Reighly formed an “anti-flirt club” to help women avoid the attention of men while out in public, mostly by educating younger women on the strategies unscrupulous men would use at the time.

    In short, men would offer women walking somewhere to drive them. A Miss Helen Brown stated in 1923, that "Too many motorists are taking advantage of the precedent established during the war by offering to take young lady pedestrians in their cars.” It would appear that some men will get very creative when it comes to obnoxious flirting.

    #4

    Men Like This, You Make Me Sick

    Text conversation depicting unpleasant approach by a man towards a woman in a chat app.

    just this morning - three separate guys on this app told me they were horny/had wood. completely unprovoked. this was the third guy, and as you can probably tell I was annoyed. it felt good typing that last message. finally deleted the app (which tbh I should've done a while ago, don't know why I didn't) but this was the final straw. men like this are truly disgusting.

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    Riley Quinn
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    I'm assuming this is a dating app where men think they can be as crass as their wee little brains want. Even if it's a "hookup" only situation, there's no need for this lewd behavior.

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    #5

    BF Doordashed Me Food, Dasher Wanted To Text His # Thinking It Was Me LOL

    Text exchange about a delivery person approaching a woman, revealing awkwardness when realizing she has a boyfriend.

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    #6

    Dug Up An Old Text I Received In 2021

    Text conversation showcasing infuriating behavior of men approaching women with unsolicited messages.

    Got takeout one day and went on public transportation with my bag of food. Already had a bad feeling, I knew I should’ve taken the receipt off. Not even sure what he looks like, but this man stole my number off of the ticket on my bag. This happened years ago, but this subreddit inspired me to find this and post it here.

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    Even more well meaning men tend to misinterpret signals all the time, through a lack of understanding context clues, lack of experience or just good old fashioned delusion. As surprising as this might seem, a woman working in a customer-facing job smiling is probably doing it because she has been told she has to.

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    Of course, many of the examples here don’t even have that plausible deniability. A delivery driver texting the number attached to the account that ordered some Door Dash is just ridiculous and gives the entire profession a bad name. Enough women have had bad experiences with this to make it more than just some isolated instances.

    #10

    My Old Neighbor Who I Considered A Friend Sent Me This Last Week

    Text message screenshot about approaching women, discussing attraction and respect.

    We have barely talked since he moved out but we used to hang out in his apartment sometimes. Officially creeped out.

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    #11

    I Didn’t Give Him My Number, He Got It From My Vacuum Rental Receipt

    Text conversation screenshot displaying a man nervously reacting after approaching a woman via text.

    After this interaction I called the rental place and told them what happened. They called back and apparently he was fired. I hope that taught him to never do this creepy stuff ever again! Also, the rental receipt literally had my address on it. Thankfully this was during a move and the paperwork had my old apartment’s address. Still so creepy to think about.

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    CaliPanda
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    None of this sh!t is new. In the dino-days before texting, I witnessed a car accident. Pulled over to help the lady who was hit. Others did a well. The speeding driver who hit her was arrested and the witnesses had to give statements on the spot. One a-hole, whom I never talked to at the scene, watched the officer write down my phone number and called me the next day, under the pretence of aligning our witness statements. Told him to f-off. The creeps keep trying - stay vigilant.

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    #12

    My Ex Texted Me At Work Asking For *pics* Thinking I Was Someone Else, And Now I Pray For Whoever Alice Is

    Text conversation depicting awkward men approaching women, featuring emojis and misunderstanding.

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    #15

    Guy Called Me This Morning Asking When I Wanted To Hook Up. I Told Him He Had The Wrong Number. I Got This Text Right After

    Text message screenshot showing a man approaching a woman with an unsolicited chat request.

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    #16

    NGVC: “Me, I’m A Nice Guy. A Gentle, Intellectual Soul…”

    Text message conversation highlights infuriating men approaching women with unwanted persistence.

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    #17

    Men, Do Not Do This. Absolutely Insane

    Text exchange depicting infuriating men approaching women through unwanted, repetitive messages.

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    Bonesko
    Community Member
    2 days ago (edited) DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    'Oh! You're in a relationship. My apologies. Just blow me' 😮‍💨

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    #19

    NGVC: “Girls Like You Are The Reason Guys Don’t Approach Females As Much These Days”

    Text messages illustrating an infuriating interaction between a man and a woman, highlighting unwanted approaches.

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    #20

    We’ve Been Divorced For 20yrs

    Text conversation illustrating men approaching women, expressing a desire to meet for closure and connection.

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    Linda Lee
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    No text reply needed but thinking: Nope. We're done. You don't get another second more of my time.

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    #21

    Saw This Guy For A Month 5 Years Ago. This Is The Past 5 Years Summed Up In 2 Photos

    Text messages showing numerous attempts of men approaching women.

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    #22

    My Childhood Friend Yall

    Text messages showing an infuriating conversation with inappropriate questions and responses between men and women.

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    Paul Scheermeijer
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    I take a shower daily or when swimming in a pool is probably not the right answer in his opinion I guess???

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    #25

    NGVC: “Fruit Of My Lions”

    Text exchanges showing awkward and infuriating men approaching women, highlighting discomfort and online interactions.

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    Tucker Cahooter
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    No, I don't think she "missed out on having a good life", I think she dodged a bullet

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    #27

    Salesperson Texted Me

    Text conversation example of men approaching women with an awkward apology and dating request.

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    Okiedokie
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Strike one: asking out a company client Strike 2: trying to play it off & THEN asking out a company client.

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    #28

    So Many Things To Unpack Here

    Infuriating online message from a man approaching a woman with inappropriate and abusive language.

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    StarCrossedFriday
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    “Be a good gril and respong!” Seriously, who advertises that they’re abusive and expects a positive reaction?

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    #29

    I Am Still Cringing

    Text conversation showing an awkward exchange of men approaching women.

    Some of the most disappointing creepy texts I've received. Was talking to this guy on tinder for several weeks and we were really hitting it off. I genuinely looked forward to talking to him every day. We moved to text messages and this happened. I had to cut communication after this.

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    Toujin C'Thlu
    Community Member
    1 day ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    I have a feeling this guy is either not actually affiliated with the BDSM community, or has been blacklisted by them

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    #33

    Guy Wants To Dox Me Because I Stopped Talking To Him, Knew Him For An Hour

    Screenshot of messages highlighting concerning behavior of men approaching women, featuring threats and aggressive language.

    There's a lot more strange messages, these are the highlights. While I truly think he is a disturbed individual who needs help, trolling is my favorite response.

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    #35

    Got Notified That I Had A Dm Request On Insta, Never Noticed These Until Today

    Repeated messages from a man approaching a woman on social media.

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    #37

    I Haven't Talked To This Man In 6 Years. I Don't Know How He Got My Number

    Text conversation showing repeated messages, highlighting infuriating men approaching women with persistence.

    I got a text from this number on valentines day saying "i'm probably the last guy you want to hear from but happy valentines day" and i assumed it was a bot so i deleted it.

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    Skogsrået
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    This guy doesn't belong on this list of pathetic cringey guys, this guy is a disgusting criminal, an actual rapist. He belongs in jail, this guy is dangerous to women all around.

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    #40

    This Creep In My Zoom Class Tried To Convince Me To Get Pregnant

    Text conversation showing someone persistently suggesting parenthood, exemplifying infuriating-men-approaching-women.

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    StarCrossedFriday
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    How is “your only purpose as a woman is to ‘bear fruit’” still a genuine thing people actually believe?

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    #41

    I'm A Recovering Anorexic

    Text conversation highlighting infuriating men approaching women, discussing body image and inappropriate comments.

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    StarCrossedFriday
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Oh, this is a new level of disgusting. He’s literally going to get some woman killed.

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    #43

    Update From My Recent Post, I Reported Him As U Guys Suggested He Didn’t Like It

    Text exchange showing aggressive, infuriating messages from a man.

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    Pink kitty
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    They told me not to contact you so I'm just going to make things worse for myself before you block me

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    #44

    Kids These Days

    Screenshot of a conversation highlighting infuriating messages between a man and woman about inappropriate content.

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    Snazzy Smurf
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    If this child is like that now, imagine some years into the future.

    #45

    NGVC: “I’m An Awesome Guy You Would Be Lucky To Have Me”

    Text messages showing an uncomfortable interaction between people, highlighting infuriating men approaching women.

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    #47

    Looking For A Room To Rent As A Young Female. Ad Has Been Up For An Hour

    Text messages illustrating inappropriate men approaching women about rental arrangements.

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    Pink kitty
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Green sounds very young and naive. I hope she doesn't get in to trouble

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    #48

    My Instagram Dm’s

    Instagram chat showing infuriating messages of a man persistently approaching a woman.

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    #50

    Nothing Has Ever Turned Me On Less Than This Pile Of Word Vomit

    Text messages illustrate awkward men approaching women, causing frustration with inappropriate comments and emojis.

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    #51

    A Person Respectfully Hit On My GF Through Instagram

    Text conversation illustrating infuriating men approaching women online.

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    Pencil
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    As a woman, I wish women would stop saying "I have a boyfriend" or "I'm married." We don't need a man for a reason. If it's a polite, respectful question, a simple "No, thank you" is enough. S**t like this doesn't merit any response at all.

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    #52

    My First Year Of Uni Is Not Going Well, Wtf Is Wrong With People

    Text conversation showing distressing messages about men approaching women inappropriately.

    my male friend gave this known creep my snap, I’m thinking of cutting him off because wtf? The creep made an alt account too so I can’t prove it was him, what do I do? I’m feeling unsafe.

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    Cee Cee
    Community Member
    2 days ago (edited) DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Delete the app of course and have serious words with your male friend.

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    #53

    Just Take A Compliment

    Text conversation highlighting infuriating men approaching women with inappropriate compliments.

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    #55

    Random Text One Of My Friends Got

    Text exchange showing an infuriating attempt by a man approaching a woman via text, despite a wrong number.

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    #59

    When I Was Going Through A Bad Break Up I Tried Using A Hotline/Anxiety App With "Professional Listeners". He Then Tried To Hit On Me

    Chat on infuriating men approaching women, highlighting frustrations and societal expectations.

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    #60

    Do I Know You?

    Text conversation showing an awkward approach by a man texting a woman about relationships.

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    #63

    NGVC: “Maybe A Nice Good Guy Is In There Waiting Talking To Himself For Months” (In Inbox)

    Text exchange illustrating infuriating men approaching women with humorous responses.

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    Wang Zhuang
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    "Out of all the men sitting in you women inbonk ya'll still choose to me single"...translation: "With all the men sitting in you women's inboxes, y'all still choose to be single." I swear I had to read this like three times to get it.

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    #65

    2 Years Later Some Random Guy I Met On A Dating App Tried Casually Hitting Me Up? Don’t Do This. He Sent The “Wyd” 15 Minutes After I Didn’t Reply To The Photo

    Text exchange depicting infuriating men approaching women, with conversation about contacting through a dating app.

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    #66

    GF Got Texted Today By This Guy

    A conversation illustrating infuriating men approaching women with persistent messages.

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    #67

    He’s Trying. Alexa Play, “The Gambler” By Kenny Rodgers

    Text message conversation showing infuriating men approaching women, with highlighted inappropriate comment.

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    #68

    Received This From A Client The Other Day. Pretty Sure He Thought He Had My Employees Personal Cell Number

    Text conversation showing an awkward encounter between a man and a woman, highlighting infuriating men approaching women.

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    #69

    NGVC: “We Tried The Nice Guy Approach That Clearly Didn’t Work”

    Text messages illustrating infuriating experiences of men approaching women, showcasing annoying conversation dynamics.

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    Anna Boes
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Socially blind here - was there a corn video of himself or was this a stupid game I don't get?

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    #70

    NGVC: "I Feel Super Played... i Guess Nice Guys Absolutely Finish Last!"

    Text conversation showing infuriating men approaching women, discussing relationship preferences and boundaries.

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    #72

    Is It Just Me Or That's Creepy? Met A Guy Online And Iam Still Confused Over Wth That Means Also Who Talks Like That

    Text message exchange demonstrating infuriating men approaching women with awkward compliments.

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    #73

    NGVC: " I Hope One Day Women Stop Leaving Nice Guys Like Me On Seen Or Opened"

    Chat screenshots depicting an infuriating conversation about men approaching women and misinterpreted replies.

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    kath morgan
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Nice guys nitpick your behaviour and believe you owe them your time. So nice.

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    #74

    Am I Overeating Or Is He Comparing Me To A Kid

    Text conversation showing infuriating dialogue of a man approaching a woman, discussing age and youthfulness.

    I've asked a few people about this and they all said i was miss interpreting it btw the dude is like 40 something. The last bit got cut off but it says children.

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    StarCrossedFriday
    Community Member
    2 days ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    In case anyone else is wondering, it says ‘drüg addícted man whöre’. And he needs watching by the police.

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