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The lack of face-to-face contact when texting can lower some folks' inhibitions (and, presumably, IQ) to such an extent that now everyone has probably had at least one encounter with someone who decided to message something that really should have been a draft.

So we’ve collected some of the weirdest, most awkward and embarrassing texts people have received and decided to share. Be warned, a very major dose of cringe incoming. If you think you are up to it, get comfortable as you scroll through, upvote your favorites and be sure to share your own examples in the comments below.

#1

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

Texts where one person rejects advances after mistaken identity

tengamtoidi Report

Sue Denham
Community Member
8 minutes ago Created by potrace 1.15, written by Peter Selinger 2001-2017

Hope Alice is able to recognise their selfishness.

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    #2

    I Accidentally Texted My Wife With Voice Recognition... While Playing The Trombone

    Screenshot of awkward text messages with repeated woo sounds and jumbled words

    JazzTrombonist Report

    Sanguina
    Community Member
    39 minutes ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I would laugh so hard if my partner did that.

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    #4

    Dad Meant To Text My Stepmom, Texted Me Instead, Then Tried To Play It Off As A Joke

    Playful and rude text exchange about appearance followed by apology

    Grimm221b Report

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    #5

    Cookies For Ranjeet

    Funny Uber Eats delivery text messages with awkward cookie comment

    byrobot Report

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    #6

    Facebook Messages From A Coworker I Had At My First Job When I Was 18. Continued To Text Me After I Didn’t Respond Until I Blocked Him

    Series of awkward repeated 'Hi' messages showing lack of response in text message screenshots

    He’s in his 40s and married.

    CygniGlide Report

    #7

    My Friend Went On A First Date A Few Days Ago. I Ask Him How It Went, And He Sends Me This Screenshot

    Lengthy and awkward text messages about dating and commitment

    ijfalk Report

    random_froggg (she/they 86/47)
    Community Member
    52 minutes ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    That’s just mean. The condescending smiley face really is the icing on the cake. OP’s friend dodged a bullet.

    #8

    Currently Sitting Alone At Home. I Was Really Excited When I Got The First Text

    Awkward texts where one blocks another after a weird love confession

    CyclicalMaestro Report

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    #9

    Sad Hang Out

    Text conversation with awkward rejection after drunken invitation

    Cease_Infidel Report

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    #10

    I Have Wished My Crush Happy Birthday For 5 Years In A Row

    Repeated awkward happy birthday texts over multiple years

    lilboreece Report

    #11

    Asked A Girl On A Date A Week Ago, And She Said Yes. Text Her Today. This Was Our Conversation

    Text message exchange with rejection and question about identity before date ask

    OrangeJuicestice Report

    #12

    I Got This Text And Instantly Felt Bad For The Guy. I'm Not Sarah

    Polite yet awkward text from Nate asking to hang out again after a date

    among_shadows Report

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    #13

    At Least She Saved His Face In Front Of His Friends

    Funny WhatsApp text where a woman rejects a man chasing above his level

    LazyGuy4U Report

    random_froggg (she/they 86/47)
    Community Member
    48 minutes ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    There was no reason to add that last part after focus on yourself except to be a jerk. Not sure what calm is supposed to be mean in this context though

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    #14

    Going To Appreciate The Honesty At Least

    Awkward text message conversation from messaging app shared online

    SHOwSHOrTAge Report

    #15

    A Creepy Text I Received From A Coworker. For More Context, I Had Purple Hair. He’s Also Got A Girlfriend! Immediately Dyed My Hair The Day After I Got This

    Lengthy poetic text message about distraction and powers in gray chat bubbles

    doonsies Report

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    #16

    Text I Got From My Friend After We Already Called And Talked The Previous Night

    Text conversation about cars leading to a girlfriend warning

    LurkerBerker Report

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    #17

    I Texted All Of My Contacts "Happy New Year"

    New Year text message with a request for a first New Year's kiss

    pseudo_potatoes Report

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    #18

    A 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 apology for wrong number followed by chat invitation

    LemonberryTea Report

    #19

    I Went On An Awkward Tinder Date With This Guy About Two Years Ago. I Had Been So Relieved After He Finally Seemed To Stop Texting Me A Year Ago. He's Back

    Text message expressing desire to talk despite being told not to with awkward reply options

    zezozose_zadfrack Report

    #20

    Blue Is My Mother. Her Husband, My Father, Died 8 Months Ago. Our New Neighbor (Grey Colored Text) Keeps Pushing A Romantic Relationship With Her

    Awkward text messages about being someone's valentine next year in funny text message screenshots

    The “I don’t think he’s all that against me” is referring to my dead father, whom he never even met.

    Tyrant2033 Report

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    #21

    Yeah, Just Got Fired, No Big Deal. Wanna Hang Out Though

    Creepy cashier texts Rachel and gets fired for invading privacy

    blackdeath29 Report

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    #22

    He Thinks He's Still At The Bar And Has To Say Things Twice And Louder For People To Hear Him

    Funny repeated text from Mason trying to remind about missed dance opportunity

    SheRatesDogs Report

    #23

    This Guy Found Me On His Wife’s “Suggested Friends” On Facebook, Then Googled Me And Used My Business Number To Text Me. Gross

    Text conversation revealing awkward message about being noticed while spouse texts

    LadyKakes Report

    #24

    My Grandpa Sent Me This Text The Other Day

    Text message from elderly man with photo and awkward greeting

    ladymoonshyne Report

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    #25

    Why Did I Even Bother Texting My Housemate About His Bottle In My Freezer Section? What Do I Even Say To Him Now?

    Text message about broken bottle and frozen chicken in fridge

    MobileAerie9918 Report

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    #26

    I Thought My Friend Was Reaching Out And Was Interested In Talking To Me

    Awkward text message exchange after sending hey to wrong person

    jarjarnotsithlord Report

    #27

    The Man I’m Talking To Sent This Without Any Context. The Toes Clenched?

    Text showing photo of legs with message questioning the thought process behind it

    banned6th Report

    #28

    To Make A Friend

    Awkward wrong number text conversation with an attempt to make a new friend

    shymusician Report

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    #29

    $1000 Tip On A $40 Meal

    Screenshot of a $1000 tip and a text message about paying rent

    ChrisMMatthews Report

    random_froggg (she/they 86/47)
    Community Member
    40 minutes ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Trinity is innocent here. OP’s uncle needs to learn he can’t buy a woman and doesn’t get to feel entitled to her because he chose to do something nice.

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    #30

    Got Stood Up On My First “First Date” Since Breaking Up With My Ex. On Valentine’s Day. He Asked Me Out On This Date

    Awkward text message exchange about sleep and meeting up that ends with no response

    Hats1889 Report

    #31

    I Just Sleep Texted My Best Friend And… What?

    Confusing text messages about book report and unclear questions

    DivaLovesWWE Report

    #32

    Why Am I So Awkward?

    Casual chat about swimming and DND in awkward text message screenshot

    For some context, I met this girl on TikTok. She’s an artist with a solid following, and honestly, her work is incredible. Somehow, I ended up in her DMs, and we started chatting. From the little we’ve talked, she comes across as incredibly smart and genuinely kind, just one of those rare people with a heart of gold.

    Now, I usually have no problem talking to people. I’m not the shy type, and starting conversations has never really been an issue for me. But for some reason, with her, I just end up feeling like some half-baked fanboy living in his mama’s basement. To make things worse, she mentioned she was tired, and there I was, still trying to keep the conversation going like a fool who didn’t get the hint.

    Extra_Spot_6686 Report

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    #34

    Virtue Signalling

    Offensive cultural appropriation accusation and humorous reply in a text message

    Aki008035 Report

    #35

    My Little Bro Borrowed My iPad To Text His Girl

    Funny romantic text messages about missing and playing grown in a SMS conversation

    honeypup Report

    #36

    These Were Taken Over The Course Of 3 Years. I Blocked Him. He’s Made About 6 New Instagram Accounts And Texted Me From Dozens Of Different Numbers

    Series of awkward breakup and apology text messages in dark mode chat screenshot

    BabyJeeb Report

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    #37

    New Guy At The Company Accidentally Sent These Texts To His Manager

    Accidental text about manager being unprofessional and apology

    Time_Advisor4822 Report

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    #38

    Just Got This Text From The Girl I’ve Been Talking To For The Past Month

    Text message about crying over someone else not texting in awkward message collection

    Yorickpeppermint Report

    #39

    We Had One Date

    Social sabotage text game causing awkward conversation

    babybird524 Report

    random_froggg (she/they 86/47)
    Community Member
    34 minutes ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    “I’m not overbearing” they say. Rightttttttt

    #40

    More Sad Than Cringe

    Tweet about cooking dinner and reading an awkward supportive text from girlfriend's mom

    e_stewartlittle Report

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    #42

    I Got An Adult Worker's Old Phone Number

    Screenshot of repeated awkward text messages asking about availability

    It's been 3 months now, and I have received well over 500+ text messages and 200+ phone calls from men asking for an adult worker on many, many websites. These screenshots are from the past month, and after me actively deleting twice as many, the same month... The majority of them are returning customers.

    Anyways, I'm about to change my phone number, but I thought this was annoying yet hilarious.

    P.S. Sometimes I would text them back with very awkward gifs, and it usually stops the madness.

    redtitz1 Report

    #43

    My Boyfriend's Creepy Dad

    Awkward flirty text where sender confesses envy and offers support

    Was at my boyfriend’s house (his dad's) earlier, and his dad always creeps me out. He must have gotten my number from my boyfriend. This was so awkward, I didn’t want to reply back so I just left it. Told my boyfriend, and he’s all "Yup, sounds like him".

    throwaway910212 Report

    random_froggg (she/they 86/47)
    Community Member
    29 minutes ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

    Didn’t read the title so when I got to the end my flabbers were ghasted and I said, “That was her boyfriend’s dad?!!?”

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    #44

    Did The Mistake Of Calling My Coworker

    Awkward coworker text where one corrects the other about being 'bro'

    No-Good-5707 Report

    #45

    Justin’s Appointment

    Funny text reply to a serious appointment confirmation message

    deleted , BSKD13 , GallowBoob Report

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    #46

    He’s Definitely Not Getting Custody

    Custody battle text messages showing a dad talking to his 11-week-old baby

    brenastii Report

    #47

    My Niece Is A Dog Walker, And She Had To Send This Message To Her Client Today

    Hilarious text message about a tampon mishap while using the bathroom

    hypersmell Report

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    #48

    My Husband Received This Message Today. We Don’t Know A “Felix”. That’s A Nasty Break, Though

    X-ray image of a broken bone shared in a WhatsApp chat

    rad504 Report

    #49

    Sent Out A Drunk Text To My Project Peer Last Night, And Just Found Out WhatsApp Won't Let You Delete Messages Older Than An Hour

    Awkward drunk confession text messages showing a big crush on WhatsApp chat screen

    unknown Report

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    #51

    He's Been Texting Me For A Full Year Now

    Awkward text messages with repeated questions and ghostbusters reference

    ppmaster6969 Report

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    #52

    Some Texts From A Psycho Ex-Boyfriend From A Little Over A Year Ago. He Was Never On Meds. He Actually Refused Them/Therapy

    Long text about breakup and mental struggles with reply saying stop calling me in awkward texts

    ashergurl Report

    #53

    My Boyfriend Broke Up With Me, Out Of The Blue, By Having A Friend Use His Phone To Text Me

    Awkward rejection text after ranting about Star Wars passion

    I was stuck in an airport alone for 8 hours after being out of the country for a week. He then blocked me before I could even answer.

    Alwaysinvisible_ Report

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    #54

    A PetSmart Cashier Used My Rewards Account To Text Me This. We Had A 5-Second Interaction

    Awkward text compliment and apology from PetSmart employee

    sad_girls_club Report

    random_froggg (she/they 86/47)
    Community Member
    20 minutes ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

    I mean I get it, but not like this. Pretty sure that’s illegal too, using work info to get someone’s phone number without permission.

    #55

    Accidentally Sent A Message Saying I Wasn’t Planning To Invite Someone… To That Exact Person. How Bad Is This?

    Group chat discussing sending invites late causing awkward conversation

    I’m part of a friend group, but there’s one person whose energy has always felt a bit off with me. It’s not an outright conflict, but she tends to get a bit exclusive within the group - like inviting everyone else and not me, or just generally making it clear I’m not really “in.”

    Recently, she posted pictures of the group and didn’t include me at all, but included a stick-figure drawing of someone who wasn’t even there, which honestly made it feel even more intentional.

    So now I have my PhD defense coming up, and I’ve been deciding who to invite. I didn’t really plan to invite her because we’re not close, and I want the day to feel comfortable.

    This morning, I was texting another friend about invites and said something like: “wasn’t planning to invite her, will send now I guess.” And accidentally sent it to her.

    She saw it.

    Jolly-Rub-3412 Report

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    #56

    Guys, I Accidentally Sent Bra Links In My Work Group Chat

    Accidental Victoria's Secret ad sent to wrong work group chat and apology

    I work at the front desk of an apt. building and like that group chat is 11 other front desk folk, mostly college kids, men and women my age, and a few older women. My one boss is like very scary and professional, and she's like early 40s, nice enough, and I don't think anyone would care, BUT I'M SO EMBARASSED.

    Lil_Towelie Report

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    #57

    HR Accidentally Sent Everyone A “Termination Notice”- Including The CEO

    Awkward work text about false termination email causing panic in group chat

    So our HR team was testing a new offboarding automation tool that sends templated “exit” emails. Someone forgot to switch from test mode to live mode.

    This morning, 300 employees (including leadership) got an email that started with:
    “Your last working day is effective immediately.”

    Slack went crazy. One manager replied, “Should I start packing?” IT had to post an all-caps message saying: “NO ONE IS FIRED. PLEASE DO NOT TURN IN YOUR BADGES.”

    I don’t think anyone’s getting actual work done today.

    Apprehensive_Show561 Report

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    #58

    The Manager Of The Cleaning Company We Use Had A Wholesome Reaction When I Accidentally Sent Her A Text Meant For My Wife

    Funny text mix-up with a cleaning appointment and mistaken identity

    Redditaurus-Rex Report

    #59

    Breaking Up Over Text Is The Worst

    Embarrassing group message revealing relationship status among multiple recipients

    Symbiotic_Tragedy Report

    #60

    Met A Cute Guy At Walmart, Exchanged Numbers. Went To Text Him This Morning And Saw My Pockets Beat Me To It. What Are My Odds Of Hearing Back From Him?

    Funny text message filled with emojis and gibberish in a chat app

    Praise-Bingus Report

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    #61

    My Mom Likes To “Accidentally” Text Me And Pretend It Was Meant For Someone Else

    Text conversation with thumbs up emojis and a message about rebellion stage

    I moved out with my boyfriend 6 months ago, and apparently, she thinks it’s a phase.

    LeeSaysHey Report

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    #62

    My Friend Met This Guy At A Bar. He Asked For Her Number Before She Left. She Said He Made Multiple Attempts From Different Numbers And Accounts

    Awkward text messages about cuddles and meeting up in Lewisville

    alinniswennis Report

    #63

    My Mom Was Texting This Guy On Bumble

    Awkward text message where one accuses other of losing interest after delayed replies

    ToothpasteCoveredDog Report