9 questions boomers ask younger people that feel more like interviews than conversations

"So, what's your five-year plan?"

I was at a family barbecue last summer, casually chatting with my uncle about my writing career, when he dropped this question like we were in the middle of a performance review. The conversation went from relaxed to rigid in seconds.

Sound familiar?

If you're a millennial or Gen Z, you've probably experienced this too. What starts as a friendly chat with someone from an older generation suddenly transforms into what feels like a job interview. You find yourself mentally preparing answers like you're defending a thesis rather than just catching up at a family gathering.

After years of navigating these interactions (especially after leaving my finance career to become a writer), I've noticed certain questions that consistently pop up. These aren't inherently bad questions, but the way they're often delivered and the expectations behind them can make younger folks feel like they're being evaluated rather than engaged with.

Let's explore the nine questions that tend to turn conversations into interrogations.

1) "When are you planning to buy a house?"

This question assumes that homeownership is still the ultimate marker of adult success, ignoring the reality that many younger people face astronomical housing prices, student debt, and a gig economy that doesn't always provide the stability banks want to see.

I remember explaining to a family friend that I actually prefer renting right now because it gives me flexibility as a writer. The look of confusion on their face was palpable. They couldn't comprehend that someone would choose not to buy property if they theoretically could.

What makes this feel like an interview question is the underlying judgment. There's often an unspoken "correct" answer they're looking for, and anything else requires justification. It turns a potential discussion about lifestyle choices and economic realities into a defense of your financial decisions.

2) "Why don't you want kids?" (Or "When are you having kids?")

This one hits close to home for me. As someone who chose not to have children, I've fielded this question more times than I can count. The follow-up questions are even worse: "But who will take care of you when you're old?" or "You'll change your mind."

What boomers often don't realize is that this deeply personal question can be painful for various reasons. Maybe someone is struggling with infertility. Maybe they can't afford children. Maybe, like me, they simply made a different choice.

The interrogation aspect comes from having to justify what should be a personal decision. You end up listing reasons like you're making a case to a jury, rather than simply having your choice respected.

3) "What exactly do you do for work?"

When I tell people I'm a writer, this question inevitably follows. But it's not asked with genuine curiosity about my craft. It's usually code for "How do you make money doing that?" or "Is that a real job?"

My mother still introduces me as "my daughter who worked in finance" rather than "my daughter the writer," as if my current career needs the validation of my former one. The subtext is clear: traditional careers are legitimate, while creative or digital careers need explanation.

For many younger people working in social media, content creation, or the gig economy, this question becomes an exhausting exercise in legitimizing their career choices to people who equate "real work" with offices and fixed schedules.

4) "How much are you putting away for retirement?"

While financial planning is important, this question often comes with assumptions about what financial security should look like. It rarely acknowledges that many younger people are dealing with student loans, rising costs of living, and wages that haven't kept pace with inflation.

When I left my six-figure salary to pursue writing, the shock from older relatives was intense. They couldn't understand prioritizing fulfillment over maximizing retirement contributions. The conversation becomes less about sharing wisdom and more about defending why you're not following their exact financial playbook.

5) "Don't you think you're on your phone too much?"

This question is particularly ironic when it comes from someone who watches cable news for hours daily. But beyond that, it shows a fundamental misunderstanding of how younger generations work, socialize, and navigate the world.

For many of us, our phones aren't just entertainment devices. They're our offices, our connection to clients, our research tools, and yes, our social lifelines. When this question is asked, it often feels like defending your entire lifestyle rather than discussing healthy tech boundaries.

6) "Why would you pay for a degree in that?"

Whether it's art history, philosophy, or gender studies, this question implies that education is only valuable if it leads directly to a high-paying job. It dismisses the value of learning for personal growth, critical thinking, or passion.

Coming from parents who were a teacher and an engineer, education was everything in my household. But it was a specific kind of education, one that led to secure, traditional careers. The interrogation feel comes from having to justify why knowledge itself might be worth pursuing, even if the ROI isn't immediately obvious.

7) "Have you tried just walking in and asking for a job?"

This question reveals how out of touch some boomers are with modern hiring practices. It usually comes with stories about how they got their job by showing up with a firm handshake and can-do attitude.

Explaining online applications, ATS systems, and the reality that most businesses don't even want walk-ins feels like teaching a masterclass rather than having a conversation. You become responsible for updating their entire understanding of the job market while defending why you can't just replicate their experience from 1978.

8) "Why do you rent when you're just throwing money away?"

Similar to the homeownership question but more accusatory, this implies financial illiteracy rather than different circumstances or priorities. It ignores maintenance costs, property taxes, the flexibility renting provides, and the barrier of down payments in today's market.

You find yourself pulling up spreadsheets and market analyses to justify what should be a simple lifestyle choice. The conversation becomes a financial audit rather than a genuine exchange of perspectives.

9) "Shouldn't you be further along by now?"

This might be the most painful question because it assumes there's a universal timeline for success. Whether it's about career advancement, relationships, or financial milestones, it measures your life against benchmarks from a different era.

At 37, when I left finance, I got versions of this constantly. The implication was that I was moving backward, that changing careers meant failing rather than growing. It turns what could be an interesting discussion about life paths into a performance review where you're always falling short.

Final thoughts

These questions often come from a place of concern or genuine interest, but the delivery and assumptions behind them create walls instead of bridges. They reflect a worldview where there's one right path to success, and deviation requires explanation.

What would happen if these questions became actual conversations? If "What do you do?" became "What excites you about your work?" If "When are you buying a house?" became "How do you like your living situation?"

The difference is curiosity versus judgment, dialogue versus interrogation. Real conversations involve listening to understand, not listening to evaluate.

Next time you're faced with one of these interview-style questions, remember that you don't owe anyone a defense of your choices. Sometimes the best response is to redirect: "That's an interesting perspective. Tell me about your experience with that."

After all, the best conversations go both ways.