For a guy whose awkward sense of humor keeps raising eyebrows, this incident in Florida this morning probably won’t help Mitt Romney’s reputation.

Mitt Romney sat at the head of the table at a coffee shop [in Tampa] on Thursday, listening to a group of unemployed Floridians explain the challenges of looking for work. When they finished, he weighed in with a predicament of his own.

“I should tell my story,” Mr. Romney said. “I’m also unemployed.”

I don’t want to sound humorless about this, and I’m sure Romney was just trying to be charming. Indeed, comments like these may very well be a deliberate self-deprecating strategy because Romney strutted around New Hampshire on Tuesday as if he’d already won the presidency, and no one likes an overconfident jerk.

But when an extremely wealthy person jokes to people who are actually struggling about being “unemployed,” it rankles. Indeed, Mitt Romney became extremely wealthy in a way that seems relevant to this discussion.

“You see, Romney made a Mittload of cash using what’s known as a leveraged buyout. He’d buy a company with ‘money borrowed against their assets, groomed them to be sold off and in the interim collect huge management fees.’ Once Mitt had control of the company, he’d cut frivolous spending like jobs, workers, employees, and jobs. […]

“Because Mitt Romney knows just how to trim the fat. He rescued businesses like Dade Behring, Stage Stories, American Pad and Paper, and GS Industries, then his company sold them for a profit of $578 million after which all of those firms declared bankruptcy. Which sounds bad, but don’t worry, almost no one worked there anymore.

“Besides, a businessman can’t be weighed down with a bleeding heart. As one former Bain employee put it, ‘It was very clinical…. Like a doctor. When the patient is dead, you just move on to the next patient.’”

Does Mitt Romney really want to joke about being “unemployed”?

To be fair, there’s at least a kernel of truth to it. Mitt Romney hasn’t worked a day in over five years — he can afford to kick back for a half-decade without breaking a sweat — but if memory serves, Romney had a job. During his brief tenure, he struggled with his duties, received poor performance evaluations, and his employers were ultimately relieved to see him quit.

Maybe Romney should mention this at his next diner stop.

Steve Benen

Follow Steve on Twitter @stevebenen. Steve Benen is a producer at MSNBC's The Rachel Maddow Show. He was the principal contributor to the Washington Monthly's Political Animal blog from August 2008 until January 2012.