Some dinner questions seem harmless—until you realize they’re quietly loaded with assumptions that don’t quite fit the world we live in now.

There’s something about sitting down for a family dinner that makes people revert to their default programming.

And for boomers? That often means diving headfirst into conversation topics that feel more like landmines than small talk.

They’re not trying to stir the pot (most of the time). In fact, many of these openers are meant to spark connection or share values. But in today’s world—where the economy’s weird, identity is fluid, and not everyone dreams of owning a house in the suburbs—they can land with a thud.

Here are seven go-to boomer conversation starters that, while well-meaning, have a special talent for making dinner a little tense.

1. “So, what do you do for a living?”

At first glance, this seems harmless. Classic icebreaker, right?

But this question assumes that everyone ties their identity to their job. Which isn’t really the vibe anymore.

In a world where people are freelancing, job-hopping, gig-working, traveling, or still figuring it out—it can feel like a loaded question. It puts pressure on the responder to either impress or defend.

I’ve watched this go down more than once at a dinner table: the moment someone says they’re “between things,” a boomer will raise an eyebrow like it’s a crime scene. Or worse, they’ll start offering unsolicited job advice based on a 1994 economy.

The truth is, work isn’t always the center of someone’s life these days. And asking this right out of the gate kind of implies it should be.

A better question? “What’s been keeping you busy lately?” It leaves room for nuance. Work, hobbies, healing, side projects—whatever matters most to the person answering.

2. “When are you going to buy a house?”

Boomers grew up during a time when buying a home was the ultimate symbol of success. But now? It’s become a punchline.

Housing prices are astronomical. Wages haven’t kept up. And for many young people, owning property just isn’t a practical—or even desirable—goal anymore.

So when this question comes up, it doesn’t feel aspirational. It feels out of touch.

It also assumes that everyone wants the same things. Some people prefer renting, living abroad, or moving often. Others don’t want the maintenance, debt, or permanence that comes with home ownership.

As noted by financial educator Ramit Sethi, “Owning a home is not always a smart investment—it’s a lifestyle choice.”

I once heard someone explain it like this: “You want me to spend half a million dollars on a house I don’t even like, just to make you feel better about where I live?”

That’s the kind of tension this question creates. And let’s be honest, even some boomers who did buy a house back then wouldn’t be able to afford their own house today.

3. “Do you have a boyfriend/girlfriend yet?”

Ah yes, the relationship interrogation.

This one tends to appear right after the mashed potatoes hit the table. And it almost always catches people off guard.

The problem isn’t just the question—it’s the implication. That being in a relationship equals progress. That being single is a phase to grow out of. That everyone is straight, monogamous, and looking to settle down.

In reality, relationships are complicated. Some people are focusing on themselves. Some are healing. Some are perfectly happy flying solo.

Others are dating… they just don’t want to bring someone into the chaos of a holiday dinner with Aunt Carol.

Plus, let’s be real—being partnered doesn’t automatically equal happiness. And being single doesn’t automatically mean someone is lost or lonely.

There’s also a growing awareness that traditional relationship paths aren’t one-size-fits-all. As psychotherapist Esther Perel has said, “We have never been more free in love—and never more confused.”

So maybe ditch the checklist mentality. Ask people what kind of connections they’re enjoying lately. You might get a way better conversation out of it.

4. “Back in my day, we didn’t have all these labels…”

This one is the verbal equivalent of stepping on a rake.

Usually it pops up during a conversation about gender, mental health, or identity. And it tends to shut things down fast.

Even if the boomer saying it doesn’t mean harm, the underlying message is: “I’m not comfortable with your reality.”

I get that things have changed fast. It can be confusing to keep up with new terms and social norms. But dismissing them as “labels” isn’t curiosity—it’s resistance.

As activist and educator Alok Vaid-Menon said: “Labels aren’t about restriction—they’re about visibility.”

People aren’t labeling themselves to complicate things. They’re doing it to feel seen. To connect with others. To build language around their experience.

This kind of comment usually turns the conversation into a debate about “how things used to be.” And sure, the past might feel simpler. But simpler doesn’t mean better. And nostalgia isn’t a free pass to invalidate what someone is going through now.

5. “How are you affording that vacation?”

This one usually starts with a compliment—“Wow, that trip looked amazing!”—but takes a sharp turn into budget policing.

Boomers love to talk about money, but they often do it in a way that’s veiled in judgment. If someone’s traveling, there must be an explanation. Are they racking up debt? Are they living off their parents?

This is especially awkward when it’s aimed at younger relatives. Because the economy that boomers thrived in? It doesn’t really exist anymore.

Travel today isn’t just for the wealthy. With remote work, travel hacking, digital nomad visas, and flexible careers—it’s more accessible than ever.

I’ve mentioned this before but the old-school script of “save, settle down, buy things” doesn’t apply across the board anymore. Not everyone wants to work 40 years to enjoy two weeks in Italy at 65.

Some people want to live now. See the world while their knees still work. And sometimes that means prioritizing experiences over a mortgage payment.

6. “No offense, but you look tired”

I don’t know why this one is still in rotation, but it is.

Boomers sometimes have this way of expressing concern that lands more like an insult.

Pointing out someone looks tired, pale, heavier, skinnier—whatever it is—usually doesn’t lead to connection. It just makes someone self-conscious.

And even if it’s meant to open the door to a conversation about health or stress, there are better ways to do that. Like maybe just asking how someone’s doing, without the side dish of critique.

As noted by Dr. Thema Bryant, psychologist and author of Homecoming, “We can care without controlling. We can check in without intruding.”

Words matter. And even if you mean well, leading with a jab rarely invites honesty.

I’ve seen this derail otherwise lovely evenings. Suddenly someone’s checking the mirror, skipping dessert, or trying to explain their sleep schedule to their cousin’s husband’s mom. No one wins.

7. “Kids these days don’t want to work”

This one’s a classic. And it never lands well.

Usually it starts with a rant about how nobody wants to do hard jobs anymore. Or how people are entitled. Or how TikTok is ruining society.

What gets missed here is context.

Yes, work ethic matters. But what boomers often don’t acknowledge is that today’s jobs come with different challenges—lower wages, less security, and burnout built into the system.

Gen Z and Millennials aren’t lazy. They’re over it.

They’ve seen what hustle culture does to people. They’re watching their parents retire late, stressed out, or sick. So they’re asking better questions about how work fits into life—not the other way around.

As writer Anne Helen Petersen puts it in Can’t Even, “Millennials were raised to be ideal workers, only to discover that the economy had no intention of rewarding them for it.”

This comment doesn’t invite dialogue. It puts people on the defensive. And it makes the generation gap feel like a chasm.

The bottom line

Most boomers don’t mean to make things awkward. They’re drawing from a script that worked in a different time.

But if we want dinner to be a space for real connection, it helps to update the dialogue.

Ask open-ended questions. Get curious instead of assumptive. Focus on how someone feels rather than what they’re doing, achieving, or buying.

Because at the end of the day, good conversations aren’t about fitting people into boxes.

They’re about letting them show up—exactly as they are.