Stacey
It’s a tale as old as time. Man meets an older woman on Tinder; man begins an intense sexual relationship with the older woman he met on Tinder; man learns that the older woman he’s been having an intense sexual relationship with is … his coworker’s mother??
Yes, that would be the record scratch moment that was sadly all too real for a Reddit user who posted his harrowing story to the social media site’s TIFU (Today I F—ked Up) subreddit.
In the post, aptly-titled, “TIFU by realizing the older woman I’ve been sleeping with for months is my coworker’s mom,” Redditor u/bleebloopo explains how he was merely looking for someone to hook up with on Tinder during quarantine.
(Which is not a good idea on any front, so perhaps this was karma?)
At any rate, the 25-year-old goes on to explain how he decided to swipe right on a “very attractive older woman” because evidently it’s the fantasy of every 20-something man to bed a smoking hot MILF.
“A few days go by and I get a notification that I have a new match,” he continues. “Wahoo! I open up the app and lo and behold it’s the fine ass cougar I was hoping for.”
“We start chatting and flirting, it’s going really well. Out of nowhere she messages me and says “I’m not sure how this app works, do we just meet to have sex or do we go on a date first?” I was drinking coffee at the time and promptly shot it out both nostrils. My chance had come. I replied back that people generally just meet up to go to the Bone Zone together but I’m easy either way. She replies “well good because I hate formalities” I nearly sh–t my pants in excitement. She sends me her address and tells me she’s free on Friday and to bring wine. The rest of that whole week was a complete blur of anxiety. I could not f—k this up.”
When Friday comes around, he shows up at the older woman’s house, and after some chit chat about music and traveling and a few glasses of wine, soon they were “full-blown going at it like rabbits [in] the middle of her living room floor.”
This goes on for several months, with the pair meeting up a couple of times a week to do the nasty, until one day OP texts her that he has the day off work and asks if he can swing by for a booty call. His cougar is DTF, but asks him to come over after 3 p.m. since her son was planning to take her to lunch.
And that is where things really go off the rails.
“So 3 p.m. comes and I’m almost at her house when she messages me that she’s running late—no problem. I park on the road and sort of just wait in my car because her car wasn’t in the driveway yet. I’m sitting there listening to the radio when an oddly familiar SUV pulls into the drive. I sorta looked at it funny and then I immediately realized where I knew it from. My coworker jumps out of the front seat, goes around to her side of the vehicle, gives her a kiss on the cheek and a hug, and then jumps back in the car. My jaw was on the ground.
He reversed out of the driveway and stupid me is sitting like a deer in the headlights in plain sight. He turns around and is literally 10 feet in front of my car and staring directly at me. My face goes bright red and I feel like I’m going to vomit. Me and this guy work together every single day and I consider him a friend of mine, I even trained him when he started at my company. And the kicker is I’ve been telling him (in detail) about this older lady and he’s been giving me immense kudos about it saying that it’s “his dream.”
He pulls up beside me and looks very confused, asks me what I’m doing and how funny it was we ran into each other. I panic completely and stumble over my words and pretend like I’m on the wrong street and trying to find my cousin’s house. He looked skeptical but sort of shrugged it off. The whole time his mother is standing there watching us through the curtains. He directs me where to go and I pull off and then circle back once he’s gone.”
Needless to say, OP says there was no “boom boom” that day, and the pair left things awkwardly—with him panicking and contemplating quitting his job.
“There’s no way he’s not going to know right? And he’s gonna realize all these wild escapades with this she-devil night mistress I’ve been telling him about is actually his mom?”
To make matters even worse, OP adds that his cougar feels guilty and wants to come clean with her son, despite the fact that he had talked to his coworker in great detail about the sexcapades, including the time he “dripped candle wax on her butthole,” because evidently “she a freak.”
Though he has not yet provided further updates, the older woman seems adamant about telling her son about their affair, but on the bright side of his imminent and untimely death, anyway, is that his tombstone will read: “Died doing what he loved best.”
Really, that’s the best any of us can hope for. But until then, at least he’s got something to talk about in the locker room.
More awkward dating stories:
- Woman’s Harrowing Story of Putting Poop In Her Purse On a Date Will Make You Stay Single
- A Woman Got Exposed Trying To Get A Free Meal And Guys Set Up A GoFundMe For Her Date
- Tinder Date Lands Girl In The ER, And Both She And Her Date Document It On TikTok
- Woman Mocked By Tinder Bro For Her Dress Gets Last Laugh When ASOS Puts Her On Their Site
- “What Is Your Tinder Horror Story?”—A Viral Thread (23 Replies)
