Aging Millennial Jokes and Fails That Will Make You Feel, Well, Like an Aging Millennial

It's certainly not the first time we've admitted here at FAIL Blog that millennials have had their day in the sun and whether we like it or not, we are no longer the center of the culture. Who would have thought that we would have to pass the torch eventually one day? I'd like to say that I hope to not have the resentment and condescension of certain generations that came before us (*cough boomers *cough), but as it turns out, it's really hard not to be at least a little resentful and condescending. 

 

These memes and tweets were compiled from @millennial_misery, @corporate_millennial_memes, and @middleclassfancy. These accounts and content creators understand the pain of nostalgia and the gradual descent toward complete and total irrelevance. For instance, I grew up saying I never wanted to be that person who had no clue who certain pop culture figures were, but these days I'm like "what is a Sumner Stroh?" Welp, keep scrolling below for these aging millennial jokes. For more content like this, check out these top trending dating fails. 

'Firing me for exposing the company's illegal activities was also illegal, so instead she raged at me' : Employee maliciously complies with terrible manager, calls IT after finding error in system, resulting in fines amounting to $30,000

Companies often cheap out on buying software, instead opting to download a pirated version for free. If this were to come to light, the fines would be hefty, but a lot of companies get away with it. This one did not. An employee with no prior office experience was hired as a processor for a mortgage company. Her boss was extremely dismissive, as she looked down on her for having no experience. Her pride cost the company $30,000 in fines.

What happened was the following: An unknown error popped up on the screen one day, and OP wasn't sure how to fix it. All she knew was that she was told 'Never to call IT'. She approached her boss, who told her literally, to call IT. OP tried arguing, but her boss was adamant. Left with no choice, OP maliciously complied; she called IT, and they were 'incredibly helpful'. In fact, they were so helpful that they asked OP to print a diagnostic page and fax it to them to see if there were any other problems, as OP was 'new'. OP did.

That left the cat out of the bag, and the next day, the manager was absolutely livid. Scroll down for a detailed account of the events. For more stories like this one, check out this woman who had enough of her messy roommates and decided it was time for revenge.

'I don't work here but can I try to help you?': Disabled customer mistakes rude Karen for a worker, most wholesome interaction ensues

Mistaking another customer for a worker is always a disastrous experience: You're embarrassed that you made a mistake, and they're confronted by the fact that someone thinks they look like a "lowly" retail worker. Depending on how much of a jerk the not-retail-worker customer actually is, they may just brush it off and leave you to stew in your embarrassment. Still, there's also the chance they explosively take offense to the situation.

When this happened to this blind customer, who had mistaken a Karen for a worker, luckily, there was another kind of customer standing by who was willing to help.

This thread emerged around a story posted to Reddit's /r/IDontWorkHereLady subreddit by Redditor u/Master-Protection-29. They shared their experience and detailed a story of a delightfully heartwarming interaction. Check out their story and see some selected screenshots below.

For more like this, 

 

'I'm not a charity': Snarky choosing beggar demands a petsitter take her dog last minute, gets completely roasted instead

Over a series of texts, this dog owner demanded a dog sitter watch her precious pooch, and she didn't bother to ask nicely. Instead, this entitled mom and dog owner tried every trick in the book to get the dog sitter to take this pup off her hands. 

Right off the bat, the conversation started with snark. The dog mom/Karen defined herself as "a potential and a little upset customer," who was annoyed that the pet sitter didn't answer her fast enough. Despite the pretentious way Karen was talking to the pet sitter, the sitter remained polite… until the very end.  

Check out this full conversation below — as some people mentioned, this conversation went on way longer than it should have, but the sitter never lost their temper. Next up, this guy had a genius workaround for his lawn work. However, his wife is far too concerned about what the neighbors would think to appreciate his brilliant plan! 

'I was that lady who checked you in last time. And I did not say that': Entitled hotel guest tries to cheat his way to a cheaper rate, gets caught in a lie

Some folks will lie, cheat, and steal to get a cheaper rate, even if the difference is just $8. Well, this guy messed with the wrong front desk employee, who proceeded to call him out and then post about it via this thread on Reddit's r/TalesFromTheFrontDesk subreddit.

 

Essentially, this dude requested two more nights at a hotel and asked for the price to match that of his last stay. Mind you, this isn't a guest with a special deal or anything because of frequent stays. He only stayed there one other time. And when he claimed that the last person at the concierge desk made this baffling "price match" promise, the Redditor revealed that they remember very clearly being that same front desk employee and made no such promise. 

 

Keep scrolling below to learn exactly how the dude reacted when he was caught in his own lie. For more, here's another story of an entitled hotel guest named Karen.

'Hate to sound picky, but...': Top 20 Choosing Beggars of the Week (March 16, 2023)

You can't just ask for free things and then throw a fit when you don't get what you wanted! But no one told that to this weeks' "choosing beggars," who are convinced the world will give them free things on a platter. 

Some people go on Facebook Marketplace or Craigslist and either beg for free stuff, or demand high discounts. There are places in the world you can get donations, so why are they trying to talk to sellers this way? Other people want creators to work for just exposure, and we all know that don't pay the rent. 

Scroll through these eye-roll inducing entitled choosing beggars. Then, check out this dude's icy revenge on his annoying neighbors.