Awkward: Jimmy Fallon’s Followers Share 40 Texting Mistakes We Wouldn’t Wish On Anyone

By Abigail T August 29, 2021

If there’s anything we’ve learned from living in the digital age, it’s that things don’t always translate over texts, tweets, or captions. Many misunderstandings – and let’s face it, Twitter wars – happen because of a lack of context, nuance, or just plain bad written communication. Also, these days, almost everyone prefers to text over calling. Partnering with the carrier T-Mobile, Jimmy Fallon asked the Internet to share their awkward text exchanges on Twitter with the hashtag #MyAwkwardTexts. The results took a deep dive into some of the most embarrassing and cringe-worthy text messages we’ve ever seen. If you’re looking for something to laugh at or die of secondhand embarrassment from, scroll down and delight in the awkward text exchanges below.

Is this girl flirting?

Someone is having some difficulty with the task of flirting over text. There is too much risk of autocorrect turning your flirty text into a morbid and embarrassing affair. Alas, what’s done is done. She really asked this guy how his stab was.

Image courtesy of Instagram/hd_kyarin; Tweet courtesy of Twitter/@Samanth56637563

We can’t begin to imagine what this guy might think the text meant. “Hey, how was the experience of being stabbed?” “Hey, how is your stab wound?” “Hey, did you manage to stab someone?” Samantha may have picked herself up off the ground, but he was probably sufficiently creeped out by that first text.

Trying too hard

Geez, how many times have you experienced this? If you’re going to hit on someone who doesn’t know who you are, at least make sure you’re a good texter. Be smooth, unlike this guy. These grammatical and spelling errors are making us cringe.

Image courtesy of Instagram/papa_andy_fanpage; Photo courtesy of Twitter/@getwiigywithit

Can this guy not take a hint? Clearly, @getwiigywithit isn’t remotely interested. She obviously couldn’t care less if he was the hottest Kevin. He should just move on and maybe work on some new pickup lines. But we do admire non-Emily’s responses and her grammar.

Wrong number

We’re all too familiar with wrong number texts. Most of the time, when we tell someone that they’ve got the wrong number, they apologize and quickly move along. But not this person. They texted the wrong number and just did not quit.

Image courtesy of Instagram/lilgemgem1; Photo courtesy of Twitter/@KMR1202

Poor @KMR1202. They had to deal with this stubborn and possibly technologically confused guy. We just wonder what made this person keep the conversation going after being told it wasn’t his aunt on the other end. Read the room, or rather, the text, and try a different number!

Reporting to the wrong chat

We’ve all experienced this at some point in our lives. Someone texts us, and we want to share it with the girls’ group chat, but we accidentally send the screenshot to the person who texted us instead. Consider yourself lucky if this hasn’t happened to you.

Image courtesy of Instagram/britneybriannetaylor; Tweet courtesy of Twitter/@paigedski

There’s a brief second when your heart stops as you realize that you sent the screenshot to the wrong person. You then push any and all buttons on your phone, trying to figure out if you can delete it before your recipient gets to read it. Did she make it?

Absurd autocorrect

You know how the iPhone autocorrect switches “omw” to an overly excited “On my way!”? It’s annoying, but it’s not too bad. What happened to @Corrinrpaul1993, on the other hand – now that’s embarrassing. Not to mention absurd. And hilarious.

Image courtesy of Instagram/graceacts; Tweet courtesy of Twitter/@Corrinrpaul1993

How does “pulling into the parking lot” automatically correct into “I’m menstruating”? This can happen only if Corrin was typing without looking at her phone and committed a ghastly typo. But hey, at least it was her brother and not someone she had a crush on.

Stranger danger

These days, you can’t just teach your children not to talk to strangers at the grocery store or the park. You have to teach them not to talk to strangers online too. So while this is an innocent mistake on this 10-year old’s part, it still shows a lot of wisdom.

Image courtesy of Instagram/madison_montes35; Tweet courtesy of Twitter/@marinersmom

He was right to ask who was talking to him, even though the person on the other line could still lie. At least he took the necessary precautions. And at least he was honest when he told his grandmother, “I thought you were a creep.”


Don’t you just love it when someone texts you about an emergency and they don’t respond to your follow-up text? Like, @AceCat33’s apartment might catch fire before she arrives home, but James doesn’t seem to think it’s all that urgent.

Image courtesy of Instagram/meganbishoppartist; Tweet courtesy of Twitter/@AceCat33

You can tell that Annaliese is panicking. All she wants is to have an apartment still to come home to after work. She’s doing all that she can do here. If James isn’t replying, it’s either he doesn’t mind the radiator breaking, or he’s already burned down with the house.

Show your what?

Sometimes you can’t take work too seriously. When you’re a little stressed out, it’s great to have a colleague who can break the tension, even if they didn’t mean to do so. Here’s a hilarious interaction between @betsyluczaj and her workmate.

Image courtesy of Instagram/graceacts; Tweet courtesy of Twitter/@betsylucjaz

Not gonna lie; we saw the word “uterus” and immediately did a double-take. Did he really mean to say that? It doesn’t matter, though, because that text single-handedly made Betsy’s drab Monday a whole lot better. We love that for her.

Cooking Mama

There is nothing worse than an inappropriate typo. Even if you set out to say something lovely and encouraging, a typo can ruin that intention. Exhibit A: this text from a son to his mother, letting her know how much people loved her potato recipe.

Image courtesy of Instagram/ishbelwatson; Tweet courtesy of Twitter/@terrylsparrow

Honestly, we don’t blame Mickey. The letters A and S are so close together on the keyboard, and the touchscreen doesn’t make it any easier! Let’s hope it was an honest mistake on Mickey’s part and not a Freudian slip.

Daddy issues

We feel terrible for this next texter, who really only wanted to be a good son and wish his dad a happy father’s day. Twitter user @Castillo_22_ was not expecting this day to be the day he finds out that his dad doesn’t even have his number saved.

Image courtesy of Instagram/Tweet courtesy of Twitter/@Castillo_22_

Imagine wishing your dad a happy father’s day over text, only to have him ask who this is. What a disappointment. We have a feeling this is going to be the start of a series of really hilarious teasing opportunities for years to come.

New phone who dis?

When an ex texts you and you don’t particularly want to engage, there is a sure-fire way to avoid the conversation completely. You don’t have to block them; you don’t even have to ignore them. Watch Twitter user @herooine teach you what to do.

Image courtesy of Instagram/the_stubbs Insta; Tweet courtesy of Twitter/@herooine

Yup, the answer is to put on your acting hat and just pretend the other person texted the wrong number, like so. The poor ex will either think he really got the wrong number or take the hint and leave you alone.


iPhone’s dictation to text feature is a tool that makes texting accessible to disabled consumers. It’s also a handy tool for people on the road but needs to reply to a text. But sometimes, speech recognition isn’t always very accurate.

Image courtesy of Instagram/simonrmatthews; Tweet courtesy of Twitter/@mrs_speech

Poor Dad was getting frustrated that the phone wasn’t recognizing his speech. What’s funny is that it is more common that we absolutely mean the other word, and autocorrect changes it. There’s always room for improvement, and perhaps Apple should take note.


It’s bad enough that people can sometimes send texts to the wrong number. But sometimes, the information received in said texts is unsolicited, and that makes it even worse. This is the stuff of texting nightmares. Take this wrong number text, for example.

Image courtesy of Instagram/fonzke_florentine_doxies; Tweet courtesy of Twitter/@raem0ndz

Yeah… nobody needed to know that you smell like beef, buddy. We can’t even begin to guess who you meant to send that text to. Who needs to know how you smell at the moment? Not a single person. TMI, man.

That’s concerning

Who doesn’t want to receive photos of kittens every once in a while? You’d be surprised how animal photos can brighten up your day. That’s probably what Twitter user @ginasopinion247’s mother thought when she sent her daughter this photo.

Image courtesy of Instagram/smithnotswift_taylor; Tweet courtesy of Twitter/@ginasopinion247

This could have been an innocent conversation had the kitten not been placed in a cooking pot atop the kitchen counter. Even worse, the answer to the follow-up question “Are you cooking it?” was “yes.” Mother, are you okay? Is the kitten okay?

… what?

On Twitter, there are those people who just tweet whatever comes to mind without a filter. It’s almost like they’re live-tweeting their daily life. Sometimes, you have friends who do the same thing. Although instead of on Twitter, they live next to you.

Image courtesy of Instagram/somebaldchick; Tweet courtesy of Twitter/@RachieFrench

That’s the only logical explanation we have for this series of texts that @RachieFrench received at 4:50 pm on a weekday. These two texts are completely unrelated to each other, and they came so close together. We also have no idea how to respond.

A monumental task

We love when grandparents are tech-savvy and with the times. This particular grandmother used her phone to text her beloved granddaughter, asking her to please write her eulogy. Not exactly something you want to hear from your grandma, or anyone.

Image courtesy of Instagram/samuel.t.basilio; Tweet courtesy of Twitter/@melissacooop

When tasked with something this monumental, to honor your grandmother in writing, you can’t say no. you can, however, respond with your initial reaction. For @melissacooop, it’s a big old “what the hell?” You can’t deny, though, that Grandma’s delivery was pretty hilarious.

Touch screen will do that

Here are just one of the reasons why you need to put a passcode on your phone, especially if you’re using a touchscreen. You might just end up sending a 10-minute voice message of yourself unloading the dishwasher. That’s just riveting.

Image courtesy of Instagram/; Tweet courtesy of Twitter/@smplcmplxity

Oh, Dad. At least it was of him in the kitchen and not somewhere awkward. But the fact that the audio message was 10 minutes long is actually pretty impressive! He really devoted himself to that dishwasher and the task at hand.

Watch your language

As a kid, you never want to make a bad impression with your friend’s parents. What if they think you’re the bad influence and forbid your friend from hanging out with you? Your friend’s parents’ impression of you determines your friendship.

Image courtesy of Instagram/canibotheryou; Tweet courtesy of Twitter/@LLAP_Idaho

Unfortunately for this kid, it looks like his friendship with Nate was short-lived. He added Nate’s mom’s number on his phone and thought it was Nate! What’s hilarious is the way he tried to cover it up with “Sorry, typo.” As if this lady is going to believe that!

Foul language

The voice text feature strikes again. This time, it riddled the lives of Twitter user @Thee_Rick_Jones and his then 15-year-old daughter Alexandra. All Rick wanted was to let his daughter know that she needed to take the bus home.

Image courtesy of Instagram/too.old.too.cold; Tweet courtesy of Twitter/@Thee_Rick_Jones

Thanks to voice texting, it made it look like Rick was calling his daughter something unseemly. Clearly, he offended Alexandra, even though he didn’t mean to. It’s a good thing Alexandra now has a car, so she doesn’t have to deal with this anymore.

Reporting to the wrong chat again

Here’s another one of the classic “reporting to the wrong chat” fiasco. It’s time we learned our lesson. Triple check before you send a screenshot to another chat. Otherwise, all the Andrews in the world is going to know that you’re talking about them.

Image courtesy of Instagram/itsdoobiedoo; Tweet courtesy of Twitter/@ngobodyy

Not that it’s a bad thing. Sometimes these dudes should know when they’re annoying, or maybe when a girl likes them and needs to confer with her squad. But to be fair on @ngobodyy, the names “Andrew” and “Angela” are alphabetically adjacent. It was an honest mistake on her part.

Protecting Yeezus

The text exchange below results from the letters “Y” and “U” close together on the QWERTY keyboard. They may only be one key apart. But Yeezus and Yeezys are two very, very different things. This one still has us giggling.

Image courtesy of Instagram/huan.g5657; Tweet courtesy of Twitter/@makenna_lg

Isn’t it the other way around? Isn’t “Yeezus” supposed to protect you instead of you protecting him? Oh, the many hilarities birthed from one simple typo. At least this typo makes you laugh instead of cringe or feel downright uncomfortable.

Sleep texting

You’ve heard of sleepwalking, but have you ever heard of sleep texting? Apparently, this Twitter user does that quite often. Of course, she doesn’t know who she texts when she does it, but this screenshot is still a comedic gem.

Image courtesy of Pinterest; Tweet courtesy of Twitter/@KatjaQueen

Imagine being the person receiving this text. You probably weren’t awake at 2:21 am, so you see this message as you wake up. Nothing about this text makes sense, so you re-read it again and again. Finally, you reply with a “Huh?”

Take the hint

So this is what it’s like to be a single girl that comes from a family that deems women should be married. You get lowkey passive-aggressive hints from your own mother. Take a look at this text and see what you think.

Tweet courtesy of Twitter/@meganfort22

Do you think @meganfort22’s mom actually committed a typo? Or did she really just want her daughter to have a spouse so she can have grandchildren? Oh, Mother. This one seems pretty clear to us. We hope that dinner turned out better than this exchange.

Location unknown

We can instantly tell the culprit of this awkward text over Craigslist. Yup. It’s your old friend autocorrect! While this feature does come in handy to avoid any errors when texting, the risk of it turning your innocent text into something weird is too great.

Image courtesy of Instagram/neurodivergentartisty; Tweet courtesy of Twitter/@DaveLowedown

We don’t understand why people just don’t turn off autocorrect. You can totally just do that in your phone’s settings. It’s a good thing this guy was just negotiating on Craigslist. Imagine the same autocorrect mishap happening when you’re texting your boss!


Whatever little nicknames or gimmicks couples share, we’re not judging. As long as they keep it in the relationship, it stays between them, and we support it. But texting can really expose someone, even when they don’t mean to be exposed.

Image courtesy of Instagram/natural_hairdom; Tweet courtesy of Twitter/@AreBu89

You can greet each other with “meow” all you want, as long as it’s to each other because other people won’t get it. Unfortunately for @AreBu89, that other person is her Certified Public Accountant. We hope things in that meeting didn’t get weird.

Is this guy flirting?

Let’s start this off with a truly awkward one. It’s every hopeless romantic’s dream to be compared to a song by someone they’re into. It’s probably their equivalent of Shakespeare’s “Shall I compare thee to a summer’s day?” But really, it depends on the song.

Image courtesy of Instagram/almost.instant.victoria; Tweet courtesy of Twitter/@ginasopinion247

Do you think this guy is flirting with @ginasopinion247? Because if he is, he needs to go away and learn some new lines. What is Gina supposed to reply to this? We’re not sure if this is flirting or cyberbullying, but it’s definitely awkward.

Boyfriend to ex real quick

The whole point of an April Fool’s joke is that it’s a joke. Unless, of course, you take it too far. But a joke isn’t supposed to come back and bite you in the backside. For Twitter user @Laki100, though, that’s exactly what happened.

Tweet courtesy of Twitter/@Laki100

It’s never a good idea to joke about cheating on someone when you’re in a relationship. It jeopardizes everything you’ve built together. This tweeter was just joking, but her boyfriend didn’t get it. He went from boyfriend to ex real quick.

Knock knock gone wrong

A knock-knock joke is one of the simplest jokes to pull off. It begins with “knock-knock” and normally hinges on a pun for its success. It’s pretty hard to get it wrong. But take a look at this exchange between siblings.

Image courtesy of Instagram/haleydarkling; Tweet courtesy of Twitter/@daxpots88

It’s one thing to get the entire order of the joke wrong. This in itself throws off the whole thing. But Josh’s texts are riddled with grammatical errors too. Little brothers think they’re hilarious, and we understand why @daxpots88 is so done.

Girls donkey

It’s always a fun time planning for a girls’ get-together. Brunch, lunch, or dinner – doesn’t matter just as long as it’s all the girls together. Well, all the girls, and a donkey, according to this text. Yeah, we were confused, too.

Image courtesy of Instagram/giavigile; Tweet courtesy of Twitter/@vicw14

What could this person possibly have typed for autocorrect to change the word to “donkey”? We’re also wondering what kind of autocorrect this person is using. Guess the donkey is coming along to dinner too! That would make for a fun story.

Should she report this to HR?

A funny nickname in the workplace is one thing. Terms of endearment are tolerable, dependent on context. But when it’s an unsolicited term of endearment coming from your boss, you can’t help but wonder… “Should I report this to HR?”

Image courtesy of Instagram/_xxs_2; Tweet courtesy of Twitter/@Nadraaaa_

This person’s boss did clarify right away that he had copied the text from a friend, so he didn’t actually mean to call her “Pumpkin.” But still, the initial shock of receiving that first text must have taken a while to wear off.

Forgot his roots?

Sometimes you’re the recipient of a wrong number text, and sometimes you are the person who texts the wrong number. Twitter user @Temoore_Raja just wanted to ask his cousin where the flashlight is, but he was met with a little hostility.

Image courtesy of Instagram/jackster1506; Tweet courtesy of Twitter/@Temoore_Raja

Apparently, his cousin changed his number after he got married and didn’t tell anyone. He probably should have told the family before they sent a stranger a selfie with an unflattering angle. No one wants to see up anyone’s nose.


It’s never the best thing to accidentally text your boss when you meant to text your boyfriend. It’s even worse when your boss is also your uncle. This Twitter user committed an awkward mistake. Thankfully her uncle had a sense of humor.

Image courtesy of Instagram/kayciebellrichard; Tweet courtesy of Twitter/@lindsayxolou

Thankfully for @lindsayxolou, the work environment also seems to be pretty chill. If this were a typical office or corporate setting, a boss would not exactly let this fly or respond with such humor. Sounds like a good work environment!

The shade

Family group chats are generally a place for central communication about basic things. Much information is exchanged there, such as who is picking up which kid from school, who needs the car on what day, and the family vacation itinerary.

Image courtesy of Instagram/sandra.diblasio; Tweet courtesy of Twitter/@iblubman

And sometimes, the family group chat is also a place to be just a little bit petty and throw shade at each other. It’s a good thing that no one took Fede’s text to heart. They’re all probably too busy being excited about the cruise to care about one little insult.

A sense of humor

The best way to play off an awkward or potentially awkward text is to just roll with it. This is where a sense of humor comes in handy, as seen in the following text exchange between a father and his daughter.

Image courtesy of Instagram/michaelpatrick1294; Tweet courtesy of Twitter/@mrs_speech

You gotta love it when your parents share a cellphone. You can’t tell who’s texting you at any given point unless they explicitly sign the text off. This dad could have easily gotten annoyed but rolled with it, and it made us laugh.

Stuck for life

Family is forever, and the same rule applies to the family group chat. Certain families update each other on everything, like getting an A on the math test or getting a new job. All @MatteaDawn wanted was to celebrate her new gig.

Image courtesy of Instagram/cruising5to1; Tweet courtesy of Twitter/@MatteaDawn

It wouldn’t be family without a little bit of banter. It’s all innocent as long as people don’t take things to heart. Jax, who we’re assuming is the brother, has actually got some zingers. We’re nonstop laughing at “Timber: The Dating App for Environmentalists.”

Potential Christmas murder?

Voice to text mishap strikes again! This time, it returns in the form of a slightly ominous text coming from a text from an aunt. Instead of wishing her nephew, Will, a good morning, she accidentally threatened to kill him on Christmas day.

Image courtesy of Instagram/graceacts; Tweet courtesy of Twitter/@S_willbeat_J

“Love you too, auntie…” Will replies to his aunt as he shouts downstairs to let his parents know he won’t be coming to the family Christmas lunch for his own good. And that was the Christmas this aunt learned never to use voice to text again.

You got the right word there?

See what we mean? The best way to handle an awkward text is to just roll with it. Laugh it off. Humor is both a defense mechanism and a weapon. If you can laugh at yourself, then you and the offender can laugh together.

Image courtesy of Instagram/tali_lasker; Tweet courtesy of Twitter/@josherwalla

@josherwalla went a step further. He didn’t just admit to Luke that he has pooped his pants in public before. By sharing this text on Twitter, with the potential to be featured on Jimmy Fallon’s show, he’s admitting this to the world!

Mom is gone

It’s always difficult to have family on the other side of the world, especially if you hear that they’re going through a tough time. The only way you can be there for them is to keep constantly updated on how they’re doing.

Image courtesy of Instagram/silvia_elizza21; Tweet courtesy of Twitter/@sararoseboyle

That’s really all Uncle John wanted – to know that his sister is okay. But his niece Sara had him believing otherwise. This is probably one of the worst autocorrect fails we’ve seen. We hope Sara wasn’t the only one who missed the text!


Nothing gets you running more than a string of texts from your mother. We’re not sure why this Twitter user’s mom didn’t just call her kids, but we’re glad that she texted because she gave us this gem of a screenshot.

Image courtesy of Instagram/inspirelytravel; Tweet courtesy of Twitter/@_WillJagner

The sense of urgency is palpable through these texts. We’re here reading through them at the edge of our seats, hoping the kids make it on the cruise on time. We’re actually screaming with the mom. “RUN, YOU GUYS. RUN!”

Thanksgiving friendliness

Have you ever been added to a group chat by accident? It’s a rare occurrence, but it does happen. It happened to Twitter user @Alisahart53 over Thanksgiving, a holiday that spreads warmth and cheer and always just a little bit of awkwardness.

Tweet courtesy of Twitter/@Alisahart53

She got added to a family group chat of a family she didn’t know, but that didn’t stop her from wishing them a happy Thanksgiving. Totally nothing wrong with that. Just trying to spread the kindness, you know? This is pretty wholesome, even if it’s awkward.