32 Suuuper Awkward Texts People Sent That Are So Bad, I Need Five Business Days To Recover From Them

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1.This person who forgot their friend was saying goodbye to her grandfather today:

Text message conversation, first person says, "I'm so bored I want to die;" response shows a photo of a person in bed with an emoji covering the face and says, "Grandpa says same;" The reply is is, "Oh my god I'm sorry."Text message conversation, first person says, "I'm so bored I want to die;" response shows a photo of a person in bed with an emoji covering the face and says, "Grandpa says same;" The reply is is, "Oh my god I'm sorry."
u/rebeccamb / Via reddit.com

2.This “accidental” text from a married neighbor:

u/ergoegthatis / Via reddit.com u/ergoegthatis / Via reddit.com
u/ergoegthatis / Via reddit.com

3.This Uber driver who crossed serious boundaries:

An Uber driver texts the passenger after the ride, the passenger says that makes women feel uncomfortable and scared, and the driver asks if she has a boyfriendAn Uber driver texts the passenger after the ride, the passenger says that makes women feel uncomfortable and scared, and the driver asks if she has a boyfriend
u/dcsabika14 / Via reddit.com

4.This MLM scammer who forgot to change her recruiting template:

The initial message invites the recipient to join a new adventure and asks if they would watch an info video; the response declines the invitation and suggests checking the template usedThe initial message invites the recipient to join a new adventure and asks if they would watch an info video; the response declines the invitation and suggests checking the template used
u/Few-Advance9654 / Via reddit.com

5.This guy who decided to show off his bank account to impress a woman:

Text message saying "hey" with a flirty emoji and a screenshot showing a bank account balance with $330.31 in checking and $4,000.00 in savingsText message saying "hey" with a flirty emoji and a screenshot showing a bank account balance with $330.31 in checking and $4,000.00 in savings
u/AsianVixen4U / Via reddit.com
Text conversation where one person tries to flirt and sends a screenshot of their bank account; the other asks why, and they respond that it's to show how much they haveText conversation where one person tries to flirt and sends a screenshot of their bank account; the other asks why, and they respond that it's to show how much they have
u/AsianVixen4U / Via reddit.com

6.This grandma who may have been trying to do a Google search:

A series of three text messages reads "how do you clean poo stains from a rug, rug stains, poo stains google"A series of three text messages reads "how do you clean poo stains from a rug, rug stains, poo stains google"
u/Sue_Flay / Via reddit.com

7.This guy who had a whole conversation with this person’s auto-reply messages:

A rude message prompts someone to set an auto response that says "hey, thanks for the message," and the rude texter keeps responding to it with increasing frustrationA rude message prompts someone to set an auto response that says "hey, thanks for the message," and the rude texter keeps responding to it with increasing frustration
u/MeowMistiDawn / Via reddit.com

8.This guy a woman met online who called her the wrong name…and then HAD to change the subject to this:

A text conversation where one person apologizes for messaging the wrong person, thinking it was Pamela; the other corrects them and says their name is not PamelaA text conversation where one person apologizes for messaging the wrong person, thinking it was Pamela; the other corrects them and says their name is not Pamela
u/Puzzleheaded_Try_200 / Via reddit.com

9.This unsuccessful opener:

A text message conversation where a tennis ball emoji appears twice: the sender apologizes for the ball, asks how the recipient is, then the recipient tells them to take it back and "have it back and f*** off"A text message conversation where a tennis ball emoji appears twice: the sender apologizes for the ball, asks how the recipient is, then the recipient tells them to take it back and "have it back and f*** off"
u/Comprehensive_Tap994 / Via reddit.com

10.This person who made this extremely awkward mistake:

When asked what they're doing, the person says they're hanging with their sick brother; the other person takes this to mean "sick" as in "cool," but they mean seriously illWhen asked what they're doing, the person says they're hanging with their sick brother; the other person takes this to mean "sick" as in "cool," but they mean seriously ill
u/turnew155 / Via reddit.com

11.This guy who went on one date with this person two YEARS ago but keeps…texting:

Text conversation showing various messages from different dates, with a guy asking to meet up repeatedly with no replyText conversation showing various messages from different dates, with a guy asking to meet up repeatedly with no reply
u/anon12xyz / Via reddit.com

12.This person who sent their dad a Father’s Day message:

Screen showing a "Love you, happy father's day" message sent within a chat app at 12:08 PM, followed by a large thumbs-up reactionScreen showing a "Love you, happy father's day" message sent within a chat app at 12:08 PM, followed by a large thumbs-up reaction
u/ashleejune / Via reddit.com

13.This guy who kept DM’ing this person then decided he “dodged a bullet”:

Text exchange: "U single?" "Nope, I have a bf" "Thank God Dodged that Bullet gg" with thumbs-up emoji reactionsText exchange: "U single?" "Nope, I have a bf" "Thank God Dodged that Bullet gg" with thumbs-up emoji reactions
u/Hornyduck0615 / Via reddit.com

14.This dad who made SURE his message was sent:

Text conversation: Dad repeatedly texts "Will pick you up" ten times; the recipient replies, "I don't think I will be up to it," then "You have texted me that 9 times now please stop;" Dad sends two more "Will pick you up."Text conversation: Dad repeatedly texts "Will pick you up" ten times; the recipient replies, "I don't think I will be up to it," then "You have texted me that 9 times now please stop;" Dad sends two more "Will pick you up."
reddit.com

15.This coworker who “accidentally” sent this message:

Text conversation discussing plans; one person invites another to a boxing event, but they can't go due to traveling to Amsterdam, the person says: "Thanks gorgeous; oops, sent that to the wrong person, sorry"Text conversation discussing plans; one person invites another to a boxing event, but they can't go due to traveling to Amsterdam, the person says: "Thanks gorgeous; oops, sent that to the wrong person, sorry"
u/ergoegthatis / Via reddit.com

16.This group leader who got jealous:

A chat conversation. One person says they were kicked out of a group for being disrespectful, and the group's owner wants to be the most liked person in the groupA chat conversation. One person says they were kicked out of a group for being disrespectful, and the group's owner wants to be the most liked person in the group
u/FOB_cures_my_sadness / Via reddit.com

17.This employee who sent this to his manager instead of his S.O.:

Someone accidentally sent their boss a text that "oh shit babe, I think I left the condom on the bathroom counter" followed by "wow, wrong person I'm so sorry"Someone accidentally sent their boss a text that "oh shit babe, I think I left the condom on the bathroom counter" followed by "wow, wrong person I'm so sorry"
u/SMDROID995 / Via reddit.com

18.This person who tried their best:

Text conversation between two people; person one says they found the other's information through social media, apologizes if it felt creepy, and then flirtsText conversation between two people; person one says they found the other's information through social media, apologizes if it felt creepy, and then flirts
u/ghost_knight_ / Via reddit.com

19.This woman who forgot she lied to this person about her number a year later:

A text from 2019 says they met at the bar last night and she gave him her number, the response says must be a wrong number; but then a year later the same number texts about a group project they're in togetherA text from 2019 says they met at the bar last night and she gave him her number, the response says must be a wrong number; but then a year later the same number texts about a group project they're in together
u/BriellaSkye / Via reddit.com

20.This person’s response after inappropriately calling someone “baby”:

The first person says "hi baby," the second says "don't call me that," and the first claims they were using speech to text and talking to their baby cousinThe first person says "hi baby," the second says "don't call me that," and the first claims they were using speech to text and talking to their baby cousin
u/paulblartmallcap / Via reddit.com

21.This person who made a joke at the wrong time:

The conversation goes like this: "Have you heard?" "That the bird is the word?" "No, Kyle died last night"The conversation goes like this: "Have you heard?" "That the bird is the word?" "No, Kyle died last night"
u/Hurkatrade / Via reddit.com

22.This Tinder match who completely misread this message:

Someone asks where their match is from, they respond Niagara, the first person misreads it as Nigeria and goes on a rant about how they don't look Nigerian and shouldn't lieSomeone asks where their match is from, they respond Niagara, the first person misreads it as Nigeria and goes on a rant about how they don't look Nigerian and shouldn't lie
u/luminabelle6 / Via reddit.com

23.This person who tried to shoot their shot and then completely denied what happened after they got rejected:

Someone says "I want you," the other person says "do not write me thing like that," and the first person claims they have never written anything to themSomeone says "I want you," the other person says "do not write me thing like that," and the first person claims they have never written anything to them
u/ergoegthatis / Via reddit.com
The first person continues by saying it couldn't have been them because they were asleep, before saying "I'll leave you alone but I don't think I was the culprit"The first person continues by saying it couldn't have been them because they were asleep, before saying "I'll leave you alone but I don't think I was the culprit"
u/ergoegthatis / Via reddit.com

24.This dad who accidentally sent this message to his stepson instead of his wife:

The screenshot shows a normal previous conversation before a message that says "shaved my balls and they feel so nice and smooth" and then an apologyThe screenshot shows a normal previous conversation before a message that says "shaved my balls and they feel so nice and smooth" and then an apology
reddit.com

25.This seriously awkward autocorrect:

A dating app conversation starts with "you've got cool outfits, do you throat a lot" and a second text changing throat to thrift with a sad emojiA dating app conversation starts with "you've got cool outfits, do you throat a lot" and a second text changing throat to thrift with a sad emoji
u/AutoCrosspostBot / Via reddit.com

26.This guy who really tried sliding into the DMs like this:

The message starts with "I believe women should be represented much better in society" before saying "Oh shit, my bad I thought I was DM'ing the homeboy"The message starts with "I believe women should be represented much better in society" before saying "Oh shit, my bad I thought I was DM'ing the homeboy"
u/bamz23 / Via reddit.com

27.This snapchatter who “doesn’t want” this person to open this photo they “accidentally” sent:

Someone sends a photo, then claims they sent it to the wrong person and asks them not to open it; when they say "OK, I won't open it" they say "You can open it if you want"Someone sends a photo, then claims they sent it to the wrong person and asks them not to open it; when they say "OK, I won't open it" they say "You can open it if you want"
u/ergoegthatis / Via reddit.com

28.This person who was just joking, of course:

The first person says "you're cute, wanna make out?" the second person says no, the first person says it was a joke, then two days later says "like I'm seriously joking"The first person says "you're cute, wanna make out?" the second person says no, the first person says it was a joke, then two days later says "like I'm seriously joking"
u/saint-cardon / Via reddit.com

29.These dudes who had a hilarious convo after one of them sent a selfie to the wrong number:

Someone starts a text convo with "good morning babe," the other person plays along but says they didn't get their selfie, so the first person sends it and asks for a selfie in returnSomeone starts a text convo with "good morning babe," the other person plays along but says they didn't get their selfie, so the first person sends it and asks for a selfie in return
u/DocdurDurf / Via reddit.com
The second person responds with a joke selfie making it clear they're someone else, the first person says "you're funny" and the second person says "I've enjoyed this moment with you"The second person responds with a joke selfie making it clear they're someone else, the first person says "you're funny" and the second person says "I've enjoyed this moment with you"
u/DocdurDurf / Via reddit.com

30.This person who purposely sent this message to their crush (who already turned them down a month ago):

The text says "I really like [name redacted] but I know he doesn't feel the same, help!" but was sent to the crush; the sender claims it was meant for their friendThe text says "I really like [name redacted] but I know he doesn't feel the same, help!" but was sent to the crush; the sender claims it was meant for their friend
u/pentapous / Via reddit.com

31.This coworker who really tried to slip this into a conversation:

In a conversation about not having a car, someone suddenly says "god I need sex, sorry I'm so frustrated"In a conversation about not having a car, someone suddenly says "god I need sex, sorry I'm so frustrated"
u/admiralasskicker / Via reddit.com

32.And finally, this cringey “prank”:

The first person claims to have become a millionaire and says "you are so fucking cute," the second person responds "thanks, my boyfriend thinks so too"The first person claims to have become a millionaire and says "you are so fucking cute," the second person responds "thanks, my boyfriend thinks so too"
u/TheTrenchCoatMafia / Via reddit.com
The first person says "I can buy you anything you want," the second says "a one-way ticket to go fuck yourself," and the first person claims this was a prank for YouTubeThe first person says "I can buy you anything you want," the second says "a one-way ticket to go fuck yourself," and the first person claims this was a prank for YouTube
u/TheTrenchCoatMafia / Via reddit.com

Whew. What’s the most awkward text you’ve ever sent? Tell us in the comments below.

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