Just hours before the first presidential debate on Thursday, Republican nominee Mitt Romney dropped in for lunch at Chipotle. He took his salad bowl to go, but stopped for a photo op with Latino workers before he did. The resulting photo, with Chipotle manager Marty Arps yucking it up for the camera, went viral instantly. For a candidate at just 21 percent among Hispanic voters according to the latest Latino Decisions/ImpreMedia tracking poll, the awkward image gave more fodder to Romney’s critics.

It’s not the first time Romney’s attempts at Latino outreach have fallen flat. Here’s a look back at six Mitt Romney gaffes in his quest to win the Latino vote.

1. Accidentally quoted Fidel Castro when talking about Cuba. Speaking before the Miami-Dade Republican Party on March of 2007, Romney launched into an attack on Venezuela’s elected strongman: “Hugo Chávez has tried to steal an inspiring phrase -- Patria o muerte, venceremos … It does not belong to him. It belongs to a free Cuba.”

The phrase means “Fatherland or death, we shall overcome” and it was popularized by former Cuban dictator Fidel Castro, who traditionally ends his speeches with it.

2. Did business with Salvadoran families tied to death squads. When Romney started raising funds for his private equity firm Bain Capital, one of the first sources he turned to were a group of Central American oligarchs that included members of the Solá, Salaverría and Dueñas families of El Salvador. It turns out they were financing paramilitary death squads.

3. Hosted rally at business owned by convicted drug smuggler. On a campaign stop in Miami, Romney held an event at Palacio de los Jugos. As first reported by the Miami New Times, the juice joint is owned by Reinaldo Bermúdez, a convicted Colombian cocaine dealer who spent three years in federal prison.

In his defense, Bermúdez told the Miami New Times he’d been vetted:

The Secret Service checked everything. [The conviction] was not a problem. Everybody deserves a second chance.

4. Accidentally said he’s a big fan of vagina. As he wrapped up an interview with Radio Mambí, Miami’s most prominent Cuban exile station, the hosts told Romney that El Palacio de los Jugos would be waiting for him with Cuban fruits like mamey and guayaba -- “Cuban fruits.” Did Romney like those fruits, they asked?

“I’m a big fan of mango, papaya and guava,” Romney said, followed by giddy laughter from the hosts.

Papaya is Cuban slang for vagina.

5. Wished he were Latino to gain votes. During a fundraiser, Romney quipped that being Latino would help him in the polls:

My dad, you probably know, was the governor of Michigan and was the head of a car company … But he was born in Mexico, and had he been born of Mexican parents, I’d have a better shot at winning this. But he was unfortunately born to Americans living in Mexico. He lived there for a number of years. And, I mean, I say that jokingly, but it would be helpful to be Latino.

Some Latinos didn’t find the joke very funny.

Critics pounced on Romney for the comments, pointing out that if he were born to Mexican parents he would have likely faced discrimination.

“Statistically, he has the golden ticket,” wrote columnist Ruben Navarette. “He's a rich white male, and they're overrepresented in the exclusive club of the 44 individuals to ever serve as president.

6. Dyed skin? Was it self tanner? Bad lighting? A makeup disaster? Two days of campaigning under the Florida sun? Likely through no fault of his own, Romney appeared at the Univision candidates' forum this month looking unnaturally orange -- feeding rumors that he had used self tanner to fit in better with Latinos.

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