40 Questions No One Over 40 Should Ask a Younger Person

"Will that internship turn into a job, y'think?"

40 Questions No One Over 40 Should Ask a Younger Person

According to an Axios poll released this April, millennials harbor some resentment toward their elders—and that’s putting it lightly.

An astonishing 51 percent of millennials surveyed said they believed baby boomers had “made things worse” for their generation. Maybe that’s a little extreme, but this general consensus has to come from somewhere. And you can take it from me, an actual younger person: I can’t help but think that some of that animosity might be linked toward older folks’ tendency to ask questions (even well-intentioned ones) that inadvertently ruffle younger people’s feathers or worse: place them in extremely awkward positions.

In short, there are just some things that you shouldn’t ask someone who happens to be two or more decades younger than you. For instance, you definitely shouldn’t ask for clarification about our lingo—especially if it concerns acronyms. Obviously judgmental, condescending questions about our finances and fashion choices aren’t exactly welcome, either. And yet, every Thanksgiving brings a new barrage of them.

So, let’s, all together now, put a stop to it once and for all. To help steer everyone toward friendly territory, here are some of the touchiest scenarios—from needless 10-year-plan needling to downright intelligence-insulting—that you really don’t have any business creating or placing yourself in.

exchanging rings at a wedding ceremony

“When are you getting married?”

As much as we may not like to admit it, a lot of us are just winging these years of our life—not to mention that asking this question of a younger person who doesn’t even have a significant other can broach particularly sensitive subjects. It’s probably best to avoid it altogether, unless you know for a fact that the person is and has been in a serious, committed, loving, stable long-term relationship.

kid in bed

“Do you want kids?”

When we’re surviving on diets of microwave meals and copious caffeine, do you really think we can devote a lot of brain- and wallet-power to whether or not we want children right now? 

man holding a camera

“You’re going to Europe! So you’re going to send us all the pictures, right?”

Nope, that’s what the Facebook photo album is for. (Trust me: you don’t want the daily overload of 100+ pictures being texted to your phone.)

man at a job interview

“Is that internship going to turn into a job?”

Talk about a touchy subject. For a lot of fields, the career ladder just isn’t what it used to be in decades past. Sometimes it doesn’t matter how hard you work during the summer or how much your bosses love you—if there isn’t money in the company’s budget to fund another entry-level salary, then a full-time job just isn’t in the cards.

i voted sticker

“Are you going to vote?”

Yeah, yeah, voting rates among millennials are lower than those of any other demographic. But there’s no need to drive the question home: we’re either going to do it or we’re not! Plus, as Jaboukie Young-White, another young person, pointed out on a recent episode of The Daily Show, Tuesdays are the hardest days to take off.

man taking money out of his wallet

“Why are you spending so much money on that?”

Whether it’s avocado toast or a tattoo you’re not fond of, we don’t really want your opinion on our extraneous expenses.

people using cell phones

“Why are you on your phone so much?”

Contrary to popular belief, we’re not spending the entirety of our time wiling away on social media. We use those devices to catch up on the news, listen to podcasts, make to-do lists, order groceries, and much more.

ripped jeans

“Why are there holes in your jeans? Did you actually pay for those?”

It’s called fashion, people.


“Why are you wearing so much makeup?”

Pointed questions like this can really prod at people’s insecurities. The fact is that some women feel best about themselves when they’re wearing a full face of makeup, while others simply love experimenting with the plethora of products available. What’s it to you if we love Sephora?

Mother Daughter Fighting

“Why aren’t you wearing makeup?”

Equally as distressing as the previous question. It’s a personal choice, and if a woman doesn’t wish to wear makeup, you definitely shouldn’t try to make her feel uncomfortable about it.

woman at computer annoyed

“How do you work Excel?”

There are so many Microsoft Office tutorials available for those who are really curious, and for the most simplistic functions in Excel, a quick search on the internet will explain how to work the program much quicker than we can.

woman looking in the mirror

“Have you gained weight?”

Honestly, it’s not advisable for you to ask anyone this question, regardless of their age.


“Is that the same boyfriend you had last year?”

The worst possible situation for this question is when a relative poses it over the holiday dinner very loudly in front of your current boyfriend, who is most definitely not the same guy you brought home last year. In those situations, all you can do is swallow a mortifying mouthful of mashed potatoes and avoid eye contact. Best to play it safe and forget the question entirely.

hair salon

“What’s your natural hair color?”

This is one of those questions that is all about how you frame it. If you present the question brusquely, we’re bound to bristle. What’s it matter to you if my hair is naturally dark brown, but I have a tendency to dye it strawberry-blonde?

mother in law with mama's boy son

“A kid out of wedlock? Really?”

A deeply personal question that likely has a convoluted answer with many intricacies and caveats. Unless you’re very, very close to the person, this question is definitely off-limits.

high school kids

“Are you excited to finally graduate and enter the real world?”

When someone’s eagerly telling you about how much they’re enjoying the classes they’re taking, this is not the way they want you to respond.

credit card

“How are you paying for that?”

Whether it’s graduate school, a new vehicle, or just a nice new wardrobe addition, critical inquiries into money management skills (or lack thereof) are likely unwanted.

broken computer

“You know how to fix this, right?”

Contrary to popular belief, being born in the digital age did not endow each and every person under 30 with a heightened Spidey-sense of technological understanding. Trust me, we’re disappointed about it, too.

daughter and father mad

“As a millennial, what’s your take on…”

It’s all in the phrasing. Don’t expect a single person to be the representative voice for an entire generation—one that encompasses a lot of disparate beliefs, experiences, and views. If you want our opinion, frame it as asking us to answer based on our own personal experiences.  

Woman holding up her college degree

“You really think that major’s going to get you a job?”

Any seasoned liberal arts student is well-accustomed to this question, ready to respond, through slightly gritted teeth, by noting the benefits of a balanced education and studying subjects that interest and excite you.


“Do you have a Tinder?”

This is necessary for you to know because…?

Graduate degree

“When are you going to graduate?”

With night classes, summer school, and part-time studies all as viable options, yes, it’s possible to receive a college diploma out of the bounds of the traditional four-year route you’re accustomed to.


“Why do you wear clothing like that?”

We wear what we want, how we want it! Keep your eyes (and thoughts) to yourself, please.

Angry Woman on Phone

“What does ‘DTF’ stand for?”

Don’t make us scramble here. “Dads That Fly?”—yeah, just…don’t.

news app millennials

“Do you even read the news?”

Could you be any more condescending? Just because younger people usually don’t pore over a print newspaper every morning at breakfast doesn’t mean they aren’t taking in the news. It’s quite the opposite, in fact. With the prevalence of push notifications, podcasts (like the New York Times‘ “The Daily”, which is exceptional), and the omnipresent News app, young people are consuming the day’s headlines voraciously—albeit not in traditional modes.

Facebook friend request

“How do I get on Facebook?”

We’re going to go out on a limb here and say that, if you can’t follow the step-by-step directions to make yourself a Facebook account, you probably don’t need one—and might not even get much out of us making one for you.

Angry Man on Phone Worst Things to Say to Customer Service

“Do you want to hear where you stack up in my will?”

We’re not as materialistic as you might think—not to mention that phrasing it that way makes it all seem a little morbid.

annoyed woman

“What do you think of ____ (insert name of family friend your mom wants to set you up with)?”

For the love of all that is good in the world, please don’t pose this question in front of said family friend’s mom. Now you’re just begging for some stuttering and straight-up awkwardness to ensue.


“What’s a Juul?”

Read the news!

Man Checking Phone During Meeting Body Language That Kills First Impressions

“Which apps should I get?”

This is one of those things you’re just going to have to feel out on your own. We can steer you clear of Snapchat and point you in the direction of the Amazon app, but we can only help you with this so much.

woman looking in the mirror

“Do I look like I’ve gained weight?”

C’mon, don’t do this to us.


“So, did you ever have a beer underage?”

Hey, let’s just focus on the present! Another round, anyone?


“What’s a Bitcoin? And how does it work?”

Chances are that we understand it about as well as you do.

Renting an apartment

“When do you plan to buy your first house?”

Well, given recent trends, it’s looking like maybe never.

Obsolete, landline phones

“What’s your landline?”

I’m sorry, my what?

Harry Potter and the Sorcerer's Stone JK Rowling Jokes From Kid's Books

“When are you going to outgrow your Harry Potter phase?”

Phase? Excuse us. This is not a “phase.” Have you outgrown your Star Wars “phase” yet?

words that reveal age, Pick-Up Lines So Bad They Might Just Work

“How do I connect to the Wifi?”

Come on: this is 101-level. You should absolutely be able to do this yourself, now.

Grandma, older mom sitting down with her grown adult daughter for a drink

“Do you remember in the ‘80s when everyone was…”

Oh—you know, grandma, I’m racking my brain, but I can’t say I do remember that time before I was even born.

confused woman

“Am I hip?”

Again, you really shouldn’t put us in this situation.


“Want to take a selfie?”

We know that’s code for: “Will you teach me how to take a selfie?” Time this question wisely; it might just depend on how high our patience levels are when you ask.

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