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63 Awkward Texts That Are So Bad It's Funny (New Pics)
Funny,FailsJUN 16, 2026

63 Awkward Texts That Are So Bad It's Funny (New Pics)

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

Dad Meant To Text My Stepmom, Texted Me Instead, Then Tried To Play It Off As A Joke
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12points

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

My Ex Texted Me At Work Asking For Pics, Thinking I Was Someone Else, And Now I Pray For Whoever Alice Is
12points

#3 Cookies For Ranjeet

Cookies For Ranjeet
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11points

#4 This Is Just Sad

This Is Just Sad
11points

#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

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.
11points

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

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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11points

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

Currently Sitting Alone At Home. I Was Really Excited When I Got The First Text
11points

#8 Sad Hang Out

Sad Hang Out
11points

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

I Have Wished My Crush Happy Birthday For 5 Years In A Row
11points

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

Asked A Girl On A Date A Week Ago, And She Said Yes. Text Her Today. This Was Our Conversation
11points

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

I Got This Text And Instantly Felt Bad For The Guy. I'm Not Sarah
11points

#12 At Least She Saved His Face In Front Of His Friends

At Least She Saved His Face In Front Of His Friends
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11points

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

I Accidentally Texted My Wife With Voice Recognition... While Playing The Trombone
11points

#14 Going To Appreciate The Honesty At Least

Going To Appreciate The Honesty At Least
10points

#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

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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10points

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

Text I Got From My Friend After We Already Called And Talked The Previous Night
10points

#17 I Texted All Of My Contacts "Happy New Year"

I Texted All Of My Contacts "Happy New Year"
10points

#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

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
10points

#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

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
10points

#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

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.
10points
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