40 Hilarious Jokes About Everyday Challenges Millennials Know Too Well

By: Lisa Lee | Last updated: Nov 06, 2023

Millennials are often stereotyped as whiny brats, but their lives have been shaped by global recessions, terror attacks, and now a pandemic. Despite their hard work and the difficulties they’ve faced, they often lack the stability and financial security to accomplish their goals. 

Yet, amidst all the negativity, millennials collectively maintain a dry sense of humor. To prove it, here are 40 jokes about millennial life that might bring a smile to your face. Enjoy some laughs, and remember, millennials deserve a break now and then!

Why Can't Millennials Afford Diamonds? 

For years, journalists were perplexed about this question – why weren’t millennials spending as much as their parents? Why weren’t they buying four-bedroom homes or throwing extravagant weddings? Above all, why weren’t they buying diamonds? 


Source: @TheEconomist/ Twitter

Thankfully, one millennial responded to a tweet about an article in The Economist, pointing out the obvious – millennials simply don’t have enough money! No longer shall we wonder why diamonds are not on the millennial menu. Now we know the answer – Millennials don’t have the budget to cover them.


How Boomers Can Help Millennials Afford a Home 

The 2008 global recession changed the economy forever. After a swirl of dodgy loans, the housing market crash left millennials in a tough spot. With home ownership out of reach, one millennial took to Twitter to voice their frustration: “If only every boomer complaining about us would give us a dollar, we could afford our own homes.” 


Source: @talzir/ Twitter

Sadly, it’s not that easy. But it does highlight how the actions of the baby boomer generation have heavily impacted the housing market. Millennials are still looking for a foothold in the market, and the dream of home ownership is slipping further away by the day.

Can Millennials Be Karens? 

Millennials are often accused of being entitled, but this tweet reveals that the “Karen” stereotype is actually based on middle-aged women. The Karen meme has become a popular way to mock people who throw a tantrum when they don’t get their way. 


Source: @LiamDrydenEtc/ Twitter

This tweet offers a new twist on the Karen meme, introducing us to Janet, who gets furious about her coupons. Could it be that boomers have got it all wrong when they accuse millennials of being entitled? Perhaps they need to look in the mirror.

What Millennial Life Is Really Like 

As a millennial, life can be a strange experience. The ability to live with friends, work remotely, and postpone starting a family is not always as grand as we imagine. We may be lucky while also feeling the effects of being “first-world poor” (i.e., we can afford the latest tech but still have empty bank accounts).


Source: @YeahimRajee/ Twitter

It’s a perplexing blend of good fortune and frustration that can leave us confused. We’re caught between the life we want and the life we have. It’s an experience that is unique to us and one that we must learn to navigate.

What Do Millennials Have to Say? 

Have you ever felt like everyone talks about you, but nobody actually asks about your life? That’s the feeling Millennials often report, as newspapers and TV shows love to debate so-called generational issues without speaking to an actual Millennial about their life. 

Source: @kbiegel/ Twitter

This can be seen clearly in the screenshot of a TV show that opted to feature Mr. Morley Winograd, who is clearly not a millennial. Here’s a novel thought: If you want to know what millennials have to say, ask a millennial, not a boomer!


Millennials: Managing Debt with Humor

For millennials, life is no joke. We’re stuck with mountains of debt, making the future a daunting prospect. But one thing that can help us get through it all is having a good sense of humor, and what better way to find that than with the hilariously inappropriate card game, Cards Against Humanity? 


Source: millenials/ Tumblr

This game, self-described as “a party game for horrible people,” asks players to match the cards in their hands with a card selected from the deck. Whoever played this card completely nailed the millennial experience and proved that even when we’re broke, we can still laugh with each other.


A Millennial's Dream Job: Emoji Translator! 

It’s no secret that many millennials are facing a difficult job market. But some have managed to snag something incredible! Take Keith Broni, for example – he’s an emoji translator! We bet you’re wondering how he got the job and if his interpretations are universal. 

Source: WtbdO/ Imgur

After all, the same upside-down smiley face can mean different things in different contexts! But we’ve got to give credit where it’s due – this is a great job for a millennial, and we’re proud of Mr. Broni for his success!


Millennials Reject Diamond Shopping Yet Again

Are millennials no longer interested in diamond shopping? It’s the question that just keeps popping up, and now the Financial Times has decided to explore the issue. According to one millennial, the cause of the problem may be the tedious online job applications that require us to enter the same information over and over. 


Source: @Steph_I_Will/ Twitter

If we could only streamline these applications, we’re sure that diamond stores would welcome the influx of young shoppers. It looks like it’s time to bid farewell to those monotonous online forms and say hello to diamond shopping!


Millennial Monopoly Hits Too Close to Home

We all love the classic board game Monopoly, but we all know the feeling when it’s over. You’re inevitably left exhausted, penniless, and quietly fuming at all the friends and family members who betrayed you and sent you broke. Sound familiar? Well, this tweet suggests it’s time to give Monopoly a millennial makeover. 

Source: @mutablejoe/ Twitter

Instead of scooping up property, we’d just pay rent – something we’re all too familiar with doing as millennials! Instead of a long, tedious, and pointless game, Millennial Monopoly promises to be an entertaining, short-lived experience that we can all relate to on a personal level.


Millennials  – Laughing All the Way to the Grave

It’s no surprise that millennials have been blamed for the end of the napkin industry, luxury goods industry, department stores, and casual dining. But what if they were also responsible for driving up funeral costs? That’s the hilarious suggestion this tweet makes, poking fun at the constant editorials that complain about millennials killing various industries. 


Source: @Internethippo/ Twitter

Although it might sound outlandish, is it that far-fetched to think millennials have the power to bring about the end of the funeral industry too? We can only joke about it – for now.


Millennial Struggles: The Reason We're Obsessed with Food 

Millennials are constantly blamed for their habits and choices, but have you ever stopped to consider why? It turns out millennials are “obsessed with food” because it’s one of the few pastimes they can afford. Think about it – millennials need food to stay alive, so it makes sense that their pastime is centered around it.

Source: @bafekidman/ Twitter

A tweet sums it up perfectly: “We’re obsessed with food because we need it to stay alive!” It’s a hard-hitting truth that many people don’t want to face, but it’s the reality that millennials have to deal with daily.


Boomers vs. Millennials: A Generation Gap That Just Won't Close

Millennials and baby boomers have long been at odds, their differing perspectives creating a generation gap that isn’t closing anytime soon. Baby boomers, born between 1946-1962, are seen as the “know-it-alls” of the world, having grown up in a time of more wealth and opportunity than ever before. 


Source: booktree.bg

Millennials, or Gen Y, have been accused of being entitled and prioritizing education over international war. In the words of a famous Tumblr joke, all we can say is, “okay, boomer.”


Millennial Frustration – A Tale of Two Generations

Struggling to find a job, saddled with student debt, and locked out of the housing market – life can be an uphill battle for millennials. But what makes it all the more frustrating is the attitude of older generations, who seem to think that the world hasn’t changed. Boomers had it easy – lifetime careers, affordable homes, and no zero-hour contracts

Source: Alamy

But times have changed, and the way millennials are treated by boomer bosses is a testament to this. Take this Tumblr post, for example, where an innocent question about food at a work event earned them the label of an entitled millennial. Clearly, there’s a huge gap between the two generations.


Dreaming of a Home: The Millennial Paradox 

For millennials, owning a house may just be a dream. With the struggle to get a mortgage, many of us remain stuck in rental properties. So, instead of daydreaming about the perfect wedding or a high-profile job, we find ourselves longing for good lighting, a decent-sized kitchen, and other features of a cozy home. 


Source: madamebomb/ Twitter

It’s almost comical how we romanticize the idea of having a basic place to live, yet as sad as it may be, it’s the reality of our generation.


Breaking Through Stereotypes: Millennials and Their Phones 

Gone are the days of generational stereotypes, especially when it comes to the millennial generation and their phones. While it’s true that millennials are glued to their screens, it’s not always for a harmful reason. 

Source: @TechnicalRon/ Twitter

Millennials are using their phones to stay connected, learn more about the world, and participate in politics and entertainment. We may joke about the differences between generations, but at the end of the day, a millennial’s phone could be a powerful tool for good.


Surviving on Air and Student Debt – The Millennial Diet 

Gone are the days of sit-down family meals, as millennials now enjoy takeout and eating on the go. But what is the true secret to surviving as a millennial? According to this post, the answer is air and student debt. 


Source: buzzfeed.com

While it may sound strange, it’s not far from the truth. Many millennials work multiple jobs, with most of their income used to pay off debt, leaving them with little time to cook meals. But that doesn’t mean millennials don’t have enough to eat – it just means they’re getting creative with their diets!


Uncovering the Cultural Differences Between Millennials and Boomers

The millennial generation is unique, with a long list of differences from the preceding generations. While their parents stayed in the same house and maintained a single career, millennials have grown up in an entirely different economic climate. This has resulted in a wide array of changes, small and large. 

Source: o.canada.com

For example, according to this ad, millennials are described as “health-care-loving-witches who don’t drive.” It’s time to explore the cultural shifts between generations and better understand the distinct characteristics of millennials!


Digital Natives vs. Boomers: Who Earns More? 

Millennials may have one advantage over boomers: technology. Growing up with the birth of the internet, they are digital natives and know their way around computers, smartphones, and other devices. 


Source: @LikwidCyance/ Twitter

But does this technical knowledge pay off? A recent tweet hilariously showed that boomers still earn more than millennials, even though they can’t use basic technology! It seems the digital natives have a way to go before they catch up to the earnings of their older counterparts.


Millennials: The Hardworking Generation 

Millennials are a generation of multi-taskers. From waitressing and retail in their teens to admin and delivery driving in their twenties, millennials juggle multiple jobs and go to school simultaneously. 

Source: weight-a-second

It’s no surprise that baby boomers fail to understand why three part-time gigs aren’t enough when you could have four. Still, resilient millennials have proven to be the hardest-working generation, showing that hard work and dedication can lead to amazing results.


Millennials Are Not to Blame for Ruining Industries

Millennials often get the blame for ruining industries like diamonds, real estate, and department stores. But, as the saying goes, “you can’t have your cake and eat it too.” The assumption that millennials have all this money sitting around is just false. Millennials live in rental apartments and are not swimming in a giant pool of cash like Scrooge McDuck. 


Source: @alketrolyat/ Twitter

So, before boomers point fingers, they should take a moment to realize that they must buy all the diamonds if they want that industry to flourish. Millennials can’t be blamed for ruining an industry they don’t care to support.


Laughing in the Face of Unfairness: The Millennial Education Dilemma 

Despite having better qualifications than previous generations, millennials often find themselves trapped in a cycle of short-term contracts featuring no benefits or long-term prospects. It’s a frustrating situation, but if we can’t find a solution, we may as well find something to laugh about! 

Source: izismile.com

This meme perfectly captures the comedic irony of the situation – while we’re complaining about housing and employment, let’s not forget to take a moment to moan about education too!


Millennial Flaws: We're Not as Practical as We Think

It’s no secret that millennials have faced many challenges, but this doesn’t make us perfect. In fact, when it comes to domestic tasks, many of us struggle to be practical. We may joke about our parents or grandparents being unable to keep up with technology, but it’s only fair to admit that we’re not perfect either. 


Source: Alamy

Perhaps it’s because our parents took care of the cooking. Or maybe it’s because we were too busy working part-time jobs in our teens to learn these skills. Whatever the reason, millennials need to recognize that we have our flaws too.


Rich Men Have Been Taking Selfies Since the 16th Century! 

For centuries, older generations have accused millennials of being too attached to their phones and taking too many selfies. But the truth is, we aren’t the first people in history to document our own images!

Source: Hanna Jameson/ Twitter

As this witty tweet reveals, rich men have been taking selfies since the 16th century – and their methods were far more elaborate than ours! From oil paintings to sculptures, wealthy men of the past went to great lengths to capture their own images. Now that’s a self-love story worth telling!


Making the Most of Millennial Life 

Being a millennial can come with its fair share of downsides, but it also has plenty of advantages. If it weren’t for smartphones and Netflix, we would miss out on a world of entertainment. Sure, we might not always be the first to accept social invitations, but that’s how it is. 


Source: @SouthernHome/ Twitter

A classic meme expresses this sentiment perfectly: we’d much rather stay in and watch the latest true crime series than go out and socialize. Nevertheless, we can make the most of millennial life with the right attitude and approach!


The High Cost of Higher Education: Millennials vs. Boomers 

Millennials receive plenty of criticism for being entitled, but what about the massive increase in the cost of education? College fees have skyrocketed since the days of the baby boomers, making it incredibly difficult for younger generations to afford higher education. 

Source: snoarkaxatives

With student debt compounding for years after graduation, it’s no surprise that millennials are feeling frustrated. Boomers, however, often view this attitude as entitled rather than pushing for more affordable tuition. Is this fair? It’s time to call for change and make higher education accessible to all.


Generational Divide: Millennials to the Rescue! 

As the internet continues to reign supreme, it’s no surprise that the war of the generations has moved online. From boomers confusing millennials with the #HowToConfuseAMillennial hashtag to Gen Z mocking millennials on TikTok, it’s evident that this generation is often misunderstood. 


Source: @calvinsharris/ Twitter

Millennials have an ace up their sleeve – their experience with the internet and new technologies. As a recent tweet pointed out, boomers may roll their eyes, but they’ll always come to millennials for help. Who else is going to help them rotate that PDF?


Avocado: The Defining Millennial Food 

The obsession with avocados is real! Every time millennials come up in conversation, avocados follow closely behind. For some reason, avocados have become the definitive millennial food, with outlets constantly discussing how millennials spend their hard-earned money on these bumpy, green, stone fruits. 

Source: @NickSplat/ Twitter

But what happens when millennials have spent all their money on luxurious green toast? They’ll be just like Tommy Pickles – left with nothing! Whether you love them or hate them, it’s clear that avocados are an integral part of the millennial experience.


"Pay Us, Please!" – Millennials Begging for Better Compensation 

Millennials are familiar with all the strange workplace trends that have taken the lead from Silicon Valley, such as hot desks and open-plan offices. But despite the perks, many millennials would rather be adequately paid for their work. 


Source: @jpbrammer/ Twitter

With the prevalence of internships and underpaid positions, many members of this generation struggle to make ends meet, and all they ask is to be paid what they deserve. Why go through the hassle of endless office trends if you won’t even receive a fair paycheck?


Catch 'em All! Millennials Rediscover Nature with Pokémon Go 

Millennials have been unfairly criticized for spending too much time on their phones. But when Pokémon Go came out in 2016, it proved that it’s possible to combine a love of technology with a love of nature. 

Source: jrpass.com

Millennials all over the world stepped out of their bedrooms and into the great outdoors, searching for digital monsters. With this game, the younger generation found a way to combine their love of technology with their love of nature. They turned a complaint into an opportunity, but still, the boomers weren’t happy. 


Taking Selfies to the Next Level 

These days, selfies are more than just a fad. People are taking them to the next level with the help of selfie sticks. Sure, it seems excessive to some, but selfie sticks are just another viable way to take a portrait. 


Source: @earlymoderation/ Twitter

Let’s face it – it’s much easier (and cheaper) to set up your phone on a stick than it is to sit still while someone paints you. Actually, scratch that – who wouldn’t want an oil painting of their latest selfie? 


Boomers Have it All: Here's Why Millennials Struggle 

The media routinely criticizes millennials, with many articles detailing their shortcomings. But the truth is, many of their struggles are rooted in the advantages their parents, the baby boomers, had. Boomers got their education for free or for a meager price, making their lives much easier and more enjoyable. 

Source: fannybawws

Just look at that baby boomer rollerblading without a care in the world. That’s the look of a man who never had to deal with thousands of dollars in student debt! While millennials may be jobless and frustrated, boomers are having the time of their lives. No wonder there’s so much bitterness among the younger generation.


Boomer vs. Millennial: Let's Swap! 

Let’s end the bickering between generations and devise a fun and creative solution. How about a full-on swap? Like the hit reality show, Wife Swap, let’s switch places and have millennials experience life as a baby boomer and vice versa. 


Source: Unsplash

We can both learn to appreciate the other’s lifestyle and understand each other better. Who knows, it could be the start of something great! So what do you say, boomers and millennials – are you ready to switch?


Millennials Hit Back at the Boomers

Millennials have a good sense of humor; this post is a perfect example! It takes a humorous jab at boomers by using the Titanic as a metaphor. We all know boomers are not fans of our phone addiction and emoji-filled conversations. 

Source: Unsplash

This poster jokingly suggested that if they were around in 1912, they would probably complain about the Titanic’s S.O.S signal being an abbreviation. It may be a little too close to home, but it’s a hilarious take on the age-old generational divide.


The Struggle Is Real: The Millennial Quest for Affordable Housing 

As millennials, we are often labeled as entitled and privileged, but the struggle to find an affordable place to live is all too real. Rent prices are ever-increasing, yet landlords still try to lease tiny homes for the same price as normal-sized ones. 


Source: Pexels

All we want is a place that doesn’t break the bank, where we can move around freely. We don’t ask for much, just a kitchen we can turn around in and a roof over our heads. Let’s face it, the quest for affordable housing is a never-ending battle.


Millennials Blamed for Killing the Snake Oil Business 

It’s a common joke to blame millennials for killing the diamond industry, the breakfast cereal industry, and even TGI Fridays. But this time, someone has taken the joke to a new level. Recent reports have blamed millennials for ending the snake oil business. Yes, you read that right. 

Source: @PastVox/ Twitter

According to the tweet, we pesky millennials have shut down the snake oil industry – who would’ve guessed? While it’s an obvious joke, and the truth is far from it, this does make for an interesting thought – what else have millennials caused to become extinct?


Boomers and Millennials: Bridging the Language Gap 

Millennials are making their mark on the way language is used in the 21st century. Growing up with new technologies has enabled us to express ourselves in ways our parents never imagined. We use emojis to convey emotion and abbreviations to type quickly. 


Source: onedio.com

Though some boomers may seem irritated by our slang, many are interested in what we have to say. By embracing millennial language, we can bridge the generational gap and create a stronger connection with our elders.


Goodbye Doorbell, Hello Smartphone 

Millennials have embraced their modern way of living, and the traditional doorbell is no exception. Smartphones have become our go-to source of communication, and if someone wants to reach us, they must call or message our cell. 

Source: @Abid_ism/ Twitter

The idea of answering the door to an unknown person is no longer appealing, with many of us preferring to stay put and find out who it is from the safety of our smartphones. From delivery notifications to home security alerts, our smartphones can do it all – goodbye doorbell, hello smartphone!


Boomers Beware: Millennials Are Here to Stay! 

It’s no secret that older generations love criticizing millennials. But this tweet takes savage aim at anyone who tries to argue against them. For this tweeter, the message is clear: boomers’ fear of getting older and fear of change is no match for millennials’ power. 


Source: @bromanconsul/ Twitter

With their avocados and student debt, they are an intimidating bunch that can’t be stopped. So, to all the boomers out there, it’s time to accept the fact that millennials are here to stay!


Millennial Frustration with Private Healthcare 

Millennials have every right to be frustrated with private healthcare. From sky-high premiums to the lack of medical coverage for those in need, it’s no wonder they’re cynical about the current system. 

Source: @samkru_/ Twitter

This tweet hilariously pokes fun at the idea that millennials are “obsessed” with public healthcare, humorously suggesting that if they need medical attention, they should just die. It’s a tongue-in-cheek jab at the boomer generation, emphasizing the need for healthcare reform.