It’s no secret that The New York Times probably runs more stories than it should that feature tantalizing material goods and experiences available only to the 1 percent.

Occasionally, the Times’ coverage is so cringe-worthy that it begs to be mocked. Consider the recent article, “When the 13-year-old Picks a $14 Million Condo.” Or last weekend’s story on the trials and travails of building one’s dream home.

And then there’s the jaw-dropping piece Cory Doctorow brought to life again on Twitter last month, a 2009 tale of bankers who were worried they couldn’t afford to live in New York City on $500,000 if bonuses were to be capped by the federal government (“You Try to Live on 500k in this town”).

This propensity for tone-deaf stories about people of vast wealth may pose a problem for the Times as it seeks to expand its digital domain. The coverage sends the wrong message for a newspaper that must attract younger readers and reinforce the unique quality of its brand for the digital future.

Consider the Gothamist response to the wealthy-children-luxury-apartment-hunting feature:

We here at Brunch Hate Reads have seen every permutation of terrible in the weekend pages of the NY Times … . As we learned from a piece today, we still have the capacity for dumb-struck awe at their ability to hold up a mirror to modern New York and only notice 1% of the reflection.

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Then there was the Sunday Gawker column that “scored” couples in the Times wedding section. Writer Katie Baker gave numerical scores to the couples based on how prestigious their schooling was, what their parents did, where they grew up, and well, how rich they sounded.

Baker wrote the column for nearly two years, and explained it in depth in a post on Grantland (including her breakdown of how she scored the couples). She wrote:

Every Sunday, the New York Times publishes the wedding announcements of the most promising, wealthy, talented—and only very occasionally inbred—couples in the whole wide world. (Oddly enough, two-thirds of them hail from within a 30-mile radius of Manhattan.) If life is a contest, these people are already winning.

The implication, of course, is that you are not.

This kind of coverage has been going on for a while at the Times. It has led to Gawker pieces like this one, and drawn ribbings in publications ranging from Wonkette to The New Republic.

And it creates a complicated response. It sparks revulsion, but also the voyeuristic tendency that might make us peek inside the windows of a gated mansion if we got the chance. There’s also a hint of aspirational fantasy: What if we lived like that?

But as the Times seeks to remain relevant to a new generation, it’s worth noting that these stories may in fact be hurting the paper’s cause, particularly when it comes to attracting older millennials between the ages of 26 and 34, like me.

We are struggling with record student loan debt, and have the unique distinction of being the first generation in recent memory to make less than our parents. We are caught in an era that pushes contract work, freelancing and temporary gigs. We are more worried about how we’re going to come up with a down payment for our first home or afford decent childcare than who will get to choose our next multimillion-dollar condo. I’d rather read stories that took these challenges on, rather than the oh-so-difficult decisions about dream houses the very wealthy might struggle to make.

Certainly, these stories get read—a lot—and show up in the “most read” list on the Times’ website with some frequency. But the Times needs to think about the larger implications of continuing to run these pieces. It’s jarring that, even now, the paper doesn’t seem to acknowledge the problems with its own elitism.

Ombudsman Margaret Sullivan recently brought up her concern about the paper’s coverage of trends and experiences available to the wealthy. But the basis of her critique was essentially affirmed by executive editor Dean Baquet.

“I think of the Times reader as very well-educated, worldly and likely affluent,” he said. “But I think we have as many college professors as Wall Street bankers.”

For its own sake, the Times needs to take a long look at its soft news and think about whether this kind of coverage helps or hurts its cause to reach new readers. I would say it hurts.

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Nikki Usher is an associate professor at The George Washington University in the School of Media and Public Affairs. She is the author of two books, Interactive Journalists: Hackers, Data, and Code and Making News at The New York Times.