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 Dad Meant To Text My Stepmom, Texted Me Instead, Then Tried To Play It Off As A Joke
Image source: Grimm221b
#2 My Ex Texted Me At Work Asking For Pics, Thinking I Was Someone Else, And Now I Pray For Whoever Alice Is
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#3 Cookies For Ranjeet
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#4 This Is Just Sad
Image source: HighlySordid
#5 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
He’s in his 40s and married.
Image source: CygniGlide
#6 My Friend Went On A First Date A Few Days Ago. I Ask Him How It Went, And He Sends Me This Screenshot
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#7 Currently Sitting Alone At Home. I Was Really Excited When I Got The First Text
Image source: CyclicalMaestro
#8 Sad Hang Out
Image source: Cease_Infidel
#9 I Have Wished My Crush Happy Birthday For 5 Years In A Row
Image source: lilboreece
#10 Asked A Girl On A Date A Week Ago, And She Said Yes. Text Her Today. This Was Our Conversation
Image source: OrangeJuicestice
#11 I Got This Text And Instantly Felt Bad For The Guy. I’m Not Sarah
Image source: among_shadows
#12 At Least She Saved His Face In Front Of His Friends
Image source: LazyGuy4U
#13 I Accidentally Texted My Wife With Voice Recognition… While Playing The Trombone
Image source: JazzTrombonist
#14 Going To Appreciate The Honesty At Least
Image source: SHOwSHOrTAge
#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
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#16 Text I Got From My Friend After We Already Called And Talked The Previous Night
Image source: LurkerBerker
#17 I Texted All Of My Contacts “Happy New Year”
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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
Image source: LemonberryTea
#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
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#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
The “I don’t think he’s all that against me” is referring to my dead father, whom he never even met.
Image source: Tyrant2033
#21 Yeah, Just Got Fired, No Big Deal. Wanna Hang Out Though
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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
Image source: SheRatesDogs
#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
Image source: LadyKakes
#24 My Grandpa Sent Me This Text The Other Day
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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?
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#26 I Thought My Friend Was Reaching Out And Was Interested In Talking To Me
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#27 The Man I’m Talking To Sent This Without Any Context. The Toes Clenched?
Image source: banned6th
#28 Justin’s Appointment
#29 To Make A Friend
Image source: shymusician
#30 $1000 Tip On A $40 Meal
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#31 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
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#32 I Just Sleep Texted My Best Friend And… What?
Image source: DivaLovesWWE
#33 Why Am I So Awkward?
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.
Image source: Extra_Spot_6686
#34 “Oh No”
Image source: papayathechicken
#35 Virtue Signalling
Image source: Aki008035
#36 My Little Bro Borrowed My iPad To Text His Girl
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#37 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
Image source: BabyJeeb
#38 New Guy At The Company Accidentally Sent These Texts To His Manager
Image source: Time_Advisor4822
#39 Just Got This Text From The Girl I’ve Been Talking To For The Past Month
Image source: Yorickpeppermint
#40 We Had One Date
Image source: babybird524
#41 More Sad Than Cringe
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#42 Definitely Deleting That Number After This
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#43 I Got An Adult Worker’s Old Phone Number
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.
Image source: redtitz1
#44 Accidentally Sent A Message Saying I Wasn’t Planning To Invite Someone… To That Exact Person. How Bad Is This?
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.
Image source: Jolly-Rub-3412
#45 Guys, I Accidentally Sent Bra Links In My Work Group Chat
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.
Image source: Lil_Towelie
#46 My Boyfriend’s Creepy Dad
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”.
Image source: throwaway910212
#47 Did The Mistake Of Calling My Coworker
Image source: No-Good-5707
#48 He’s Definitely Not Getting Custody
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#49 My Niece Is A Dog Walker, And She Had To Send This Message To Her Client Today
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#50 My Husband Received This Message Today. We Don’t Know A “Felix”. That’s A Nasty Break, Though
Image source: rad504
#51 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
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#52 Really?
Image source: Significant-Soups
#53 He’s Been Texting Me For A Full Year Now
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#54 Some Texts From A Psycho Ex-Boyfriend From A Little Over A Year Ago. He Was Never On Meds. He Actually Refused Them/Therapy
Image source: ashergurl
#55 My Boyfriend Broke Up With Me, Out Of The Blue, By Having A Friend Use His Phone To Text Me
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.
Image source: Alwaysinvisible_
#56 A PetSmart Cashier Used My Rewards Account To Text Me This. We Had A 5-Second Interaction
Image source: sad_girls_club
#57 HR Accidentally Sent Everyone A “Termination Notice”- Including The CEO
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.
Image source: Apprehensive_Show561
#58 The Manager Of The Cleaning Company We Use Had A Wholesome Reaction When I Accidentally Sent Her A Text Meant For My Wife
Image source: Redditaurus-Rex
#59 Breaking Up Over Text Is The Worst
Image source: Symbiotic_Tragedy
#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?
Image source: Praise-Bingus
#61 My Mom Likes To “Accidentally” Text Me And Pretend It Was Meant For Someone Else
I moved out with my boyfriend 6 months ago, and apparently, she thinks it’s a phase.
Image source: LeeSaysHey
#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
Image source: alinniswennis
#63 My Mom Was Texting This Guy On Bumble
Image source: ToothpasteCoveredDog
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