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

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."
u/rebeccamb / Via reddit.com

2.This "accidental" text from a married neighbor:

  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 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 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 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 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"
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 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 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"
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 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 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 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 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."

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"
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 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"
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 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 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 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"
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 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 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"
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 apology

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 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"
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"
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"
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 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"
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 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"
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"
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 YouTube
u/TheTrenchCoatMafia / Via reddit.com

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