Generation Y takes unemployment with equal parts self-obsession and guilt.

A few weeks ago, a Facebook status update announced that my friend—let's call her Dorothy—had received her first unemployment check. I clicked on some pictures expecting to see tears and instead saw her drinking Red Bull and flashing her pearly whites. The photographs were presumably taken after she lost her job since, in New York, the first unemployment checks take between three weeks and two months to arrive. After I logged off, the images lingered like an unfinished equation.

With some wonder, I started seeking out stories that, in a few short strokes, fulfilled every negative stereotype associated with Generation Y, the so-called entitlement generation. They're easy to find. One unemployed Gen Yer is living out a life dream, traveling India and paying for hostels with unemployment checks. A particularly desperate male had to actually move back into his parents' beautiful two-story house in Connecticut and is on a weekly allowance from the state. What's striking is that the stories are told with refreshing honesty; there appears to be no real effort to mask anything. "I was trying to find another job, but I was being very selective," says a mid-20s male who was laid off from a job in L.A.'s music industry in early 2008 and who collected unemployment for six months. "I was, admittedly, being a pompous prick."

The stories continued, some with genuine guilt about receiving public benefits. "I collected unemployment for two months, and I felt incredibly guilty. Is that the norm?" asks a mid-20s female elementary-school teacher living in Montana. She described a number of people who live in her mountain town who work seasonal jobs and collect unemployment the rest of the year. The guilt came up again. "I do feel guilty. I do. I heard New York has to borrow something like $100 million from the government to pay for everyone on unemployment," says a mid-20s male who worked in telecommunications in Chicago and New York. He continued, "I was laid off in 2007, and I didn't collect unemployment because I thought I was too good to collect it. I didn't want to be a drain on the economy." That was before his family lost 90 percent of their net worth with Madoff. Even now, he admits, "I haven't even gotten the rude awakening yet." This last story is from one of my good friends, and I asked him if I could include it. "Sure. Mention it all. Just don't use my name. Slam us."

Generation Y grew up in the '80s and '90s; when we're classified by academic studies and articles we are, at our best, more civic-minded, more progressive, more community-oriented, more interested in the work-life balance than the generation before us. At our worst, we're arrogant, spoiled, and immature. Who can blame us? When the recession officially began in December 2007, everyone on the Forbes 400 list was a billionaire and The Apprentice was beginning its sixth season. How could there be anything but a thin awareness of real financial hardship? Go down the list of the things that occupied the cultural imagination during these decades. Start with Baby Jessica and stop when you get to Ritalin. The reality today is not ignorance or even materialism. It's merely a potentially devastating unseriousness, like listing lying as one's favorite activity on Facebook.

Consider the financial sector, past and present. The year the ship started to sink, 58 percent of the males in Harvard's graduating class accepted jobs in finance and earned twice as much as graduates working in other industries. By comparison, 1980—the birth year that roughly marks the beginning of this generation—shows an equal distribution of salary between financial and nonfinancial industries. Although the number in the Masters of the Universe club is dwindling every day, most still have more savings than their neighbors, a piece of valuable art, a $500 tie. Some think they got a good arrangement. "So many people are getting laid off that are married with kids. I'm getting laid off because I hate my job and in the process, I get severance and I get unemployment," says one mid-20s male who lost his job this month. "It's crazy if you think about it, that I qualify for the same thing."

This is not a memo against unemployment benefits for Generation Y. The unemployment program is a product of Franklin Roosevelt's New Deal, meant to act as an automatic stabilizer to the economy and provide unemployed workers with temporary relief. As we move closer to our own Great Depression, "stabilizing" and "temporary relief" make a lot of sense. As for Gen Y, why shouldn't we receive our fair share, as well? After all, these employees paid unemployment taxes to their employers, who paid taxes to the state. But then re-examine the original premise of unemployment insurance: to assist with basic needs. There is a surreal disconnect between the privileged unemployed and President Obama's recent injunction to the young and suffering to endure, to rise up, because not to means: "It's not just quitting on yourself, it's quitting on your country."