Alright, buckle up! Today, we're diving into some of the wildest, weirdest, and downright awkward encounters women have had with guys sliding into their DMs like it's the year 2005. Think unsolicited messages, awkward trying-too-hard pickup lines, and epic comebacks. Let’s get right to these cringetastic moments!
This post may include affiliate links.
Mr. Shy Guy’s Not-So-Shy Act
Slicing Through the Creepiness
Just Your Everyday Halloween Creep
When someone barely knows you but messages like you’re soulmates? Yup, that's a fun way to spot a potential stalker. Spoiler: Spam texts and clingy calls aren’t cute, no matter how much they say it’s 'love.'
Heads up! Bombarding someone with texts is a classic stalking move. Totally terrifying, even if it’s not face-to-face.
"Sorry About Your Sister, But Are You Single?"
Did He Think I Was Clueless? Spoiler: Nope.
On Vision and Boundaries
We’re talking weird pics, nonstop questions about your whereabouts, and ignoring the big flashing neon NO YOU SENT THEM. Red flag alert!
Because guessing games are lame: if they keep pushing after you’ve dropped the 'do not contact' bomb, it’s time to peace out.
Ladies, Meet Mr. 'On The Market'
When Your Much Older Coworker Can't Take a Hint
This dude was moved to another store because, surprise, he’s creepy and can’t quit fights with his ex. Now he’s targeting me. Manager meeting ASAP because nope!
Dating as a Black Woman? Brace Yourself
And it’s not just texts. Unwanted calls? Also stalking, not just clingy. Some folks think their ‘love’ means calling 30 times a day. Spoiler: Nope.
Yup, obsession and ignoring a clear NO isn’t romantic - it’s creepy.
Woke Up To This... And Nope, Didn't Go Back To Sleep
Girl I Went On Two Dates With: The Saga Ends
Told her I wasn’t interested a week ago... finally had to block her. Drama level: high.
From Work Chat to Panties Talk in Seconds Flat
Then, we've got the full horror movie plot: creepy gifts, online smear campaigns, property damage, and high-tech stalking gadgets. Yes, really. This isn’t fiction; some folks go there.
Bonus nightmare: they show up where you hang out, bug your devices, or stick trackers on your car. Yikes!
Older Guy From Work Asked Me Out When I Was a Teen
This guy was way older and asked me out when I was still a teenager. Creepy vibes all around. I blocked him ages ago but bumping into him in the grocery store gave me a real-life scare.
Creepy Old Housemate After I Gave Him My Number
The Younger Generation Is Scaring Me
If you’re ever in the cyber-stalking zone, note this: save everything! Messages, screenshots, all of it. That way, you have ammo for the police or social media to catch the creeps, even if they try to vanish.
If it gets scary quick, call the authorities ASAP. Otherwise, reporting is still a smart move.
Why Can't Men Over 50 Take a No?
Poor Dude Didn’t Know What Hit Him
Reply to My Comment on Age Gaps That Made Me Go Ew
Step up your online security game: strong passwords, two-factor authentication, and cleaning up your digital footprints are the new must-haves. Google yourself - yes, that’s a real strategy to keep the creepers at bay!
Reminder: if you’ve been targeted, it’s NOT your fault. None of it.
I Feel Uncomfortable... And You Should Too
Being a Plus-Sized Girl Online? Welcome to This Message
Short story: I asked this guy how he found my Snapchat, and his reply was... nope. Nope nope.
Respectfully… The Worst Opener Ever
Welcome to the 'Creepy PMs' club - where people share those head-scratching, facepalm-worthy, and bone-chilling messages from internet weirdos. From mildly weird to full-on nightmare fuel, it’s all here.
This subreddit has been running strong for years, pulling in thousands of people ready to shame the creeps every week.
I Think I Hit a Nerve… And It Was Priceless
Girl Added Me and Sent This After I Said No
Left Him on Delivered for 3 Hours—This Was the Reaction
Matched this guy on Hinge yesterday, and dude went all pet names instantly. Left him hanging for 3 hours, and this message popped up. Bro, we haven’t even talked for a day!
Posting rules? Cover names and faces to protect privacy. Wednesdays are wildcard days - think memes and icy chat app drama!
To Be Fair, I Was Wearing Fishnets
This Made Me Laugh for Real
Sent This Gem From a 52-Year-Old Colleague With Teen Kids
Reminder: Be kind! No roasting the people sharing their cringe stories. Zero blaming victims or trying to psychoanalyze on the fly. And definitely no creepy flirting in the comments. Let’s keep it fun and supportive, folks.
This Broke Her Brain (In a Hilarious Way)
I Know This Is Grindr, But Come On Man
Creepy Way to Start a Chat? You Bet!
So, what’s the weirdest, creepiest message YOU ever got? How’d you handle it? Feel free to spill the tea in the comments and share your own wild stories!
Oops, Got Another One
Loser Deleted His Message—Had to Laugh
Phew... Bullet Dodged!
I Wanna Hear You Say It...
What the Heck?!
One of the Worst Questions Ever Asked
"Are You Lactate?" What Even?
First Time on the Apps and This Happens (Classic)
My Very Own Reddit Stalker!
"Gooning A Lot"? Umm, Okay...
Started chatting and this gem dropped casually in the intro. Literally took me a second to process.
Creepy Message From Ex of My Deceased Best Friend
This guy dated my bestie before she passed. Years later, he messages me out of nowhere, despite knowing I’m engaged and pregnant. Mind = blown (and nope!).
"Why You Ignoring Me?" Nah, Just Nope.
Not So Creepy, Just Plain Weird (He’s 40, I’m 20)
My Dad Sent Me This Text (I'm 34) — Yikes
Trying to avoid my dad, but he drops texts like this. Grew up with a trucker dad, so... complicated. This one? Definitely the creepiest yet.

37
0