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

© Photo: JazzTrombonist
#2 Justin’s Appointment

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

© Photo: User
#4 The Manager Of The Cleaning Company We Use Had A Wholesome Reaction When I Accidentally Sent Her A Text Meant For My Wife

© Photo: Redditaurus-Rex
#5 He’s Definitely Not Getting Custody

© Photo: brenastii
#6 Cookies For Ranjeet

© Photo: byrobot
#7 More Sad Than Cringe

© Photo: e_stewartlittle
#8 This Is Just Sad

© Photo: HighlySordid
#9 Asked A [intimacy] A Date A Week Ago, And She Said Yes. Text Her Today. This Was Our Conversation

© Photo: OrangeJuicestice
#10 Breaking Up Over Text Is The Worst

© Photo: Symbiotic_Tragedy
#11 Virtue Signalling

© Photo: Aki008035
#12 I Just Sleep Texted My Best Friend And… What?

© Photo: DivaLovesWWE
#13 Currently Sitting Alone At Home. I Was Really Excited When I Got The First Text

© Photo: CyclicalMaestro
#14 Sad Hang Out

© Photo: User
#15 The Man I’m Talking To Sent This Without Any Context. The Toes Clenched?

© Photo: User
#16 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

© Photo: Hats1889
#17 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

© Photo: zezozose_zadfrack
#18 I Have Wished My Crush Happy Birthday For 5 Years In A Row

© Photo: lilboreece
#19 He Thinks He's Still At The Bar And Has To Say Things Twice And Louder For People To Hear Him

© Photo: User
#20 Why Did I Even Bother Texting My Housemate About His Bottle In My Freezer Section? What Do I Even Say To Him Now?

© Photo: MobileAerie9918
#21 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.

© Photo: CygniGlide
#22 I Got This Text And Instantly Felt Bad For The Guy. I'm Not Sarah

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#23 To Make A Friend

© Photo: shymusician
#24 At Least She Saved His Face In Front Of His Friends

© Photo: LazyGuy4U
#25 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?

© Photo: Praise-Bingus
#26 I Texted All Of My Contacts "Happy New Year"

© Photo: pseudo_potatoes
#27 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

© Photo: LemonberryTea
#28 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.

© Photo: Tyrant2033
#29 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

© Photo: alinniswennis
#30 My Grandpa Sent Me This Text The Other Day

© Photo: ladymoonshyne
#31 $1000 Tip On A $40 Meal

© Photo: ChrisMMatthews
#32 Why Am I So Awkward?
For some context, I met this [intimacy] 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.

© Photo: Extra_Spot_6686
#33 Going To Appreciate The Honesty At Least

© Photo: User
#34 Just Got This Text From The Girl I’ve Been Talking To For The Past Month

© Photo: Yorickpeppermint
#35 Definitely Deleting That Number After This

© Photo: ttv_ninjrr
#36 My Mom Was Texting This Guy On Bumble

© Photo: User
#37 My Husband Received This Message Today. We Don’t Know A “Felix”. That’s A Nasty Break, Though

© Photo: User
#38 "Oh No"

© Photo: papayathechicken
#39 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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#40 New Guy At The Company Accidentally Sent These Texts To His Manager

© Photo: Time_Advisor4822
#41 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.

© Photo: Alwaysinvisible_
#42 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.

© Photo: Jolly-Rub-3412
#43 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.

© Photo: Apprehensive_Show561
#44 He's Been Texting Me For A Full Year Now

© Photo: User
#45 A PetSmart Cashier Used My Rewards Account To Text Me This. We Had A 5-Second Interaction

© Photo: User
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