By Scott Conroy - November 16, 2012

On a chilly late-January afternoon in 2008, Mitt Romney was engaged in yet another day of around-the-clock campaigning when he posed for a photo with a group of young African-Americans at a Martin Luther King Day parade in Jacksonville, Fla.

It was my fifth month on the trail with Romney as an embedded campaign reporter for CBS News but the first time I had seen him at an event attended by more than a few minorities.

In all likelihood, not many of those at the MLK parade voted for Romney in the Florida primary the following week, but he was nonetheless greeted warmly by just about everyone he encountered.

The teenagers with whom the former Massachusetts governor posed seemed particularly excited to meet a famous person, as one young woman cheered and draped her arm around the candidate.

“Who’s got your camera though?” Romney asked as he scanned the crowd, looking for someone to snap the shot.

There was a brief pause, and then he bellowed:

“Who let the dogs out? Who?! Who?!”

The shirt-and-tie-clad candidate’s outburst referenced an eight-year-old song from a one-hit wonder; it had once so saturated the airwaves that a poll conducted the previous month by Rolling Stone magazine ranked it the third most annoying song of all time.

A few of the kids in the crowd giggled nervously at Romney’s non sequitur before the candidate told them, “Thanks, guys,” and moved along.

A few minutes later, a baby was hoisted up for the most standard of campaign trail rituals: politician-meets-infant photo op. But Romney took the moment to make yet another outdated, and perhaps even more cringe-worthy, reference to urban pop culture.

“Hey, buddy, how you doing? What’s happening?” Romney said to the African-American child. “You’ve got some bling-bling there, too!”

In the countless hours I spent in Romney’s presence during his first White House run (and mostly from a greater distance during his second bid), I saw a man who was preternaturally upbeat, well-meaning, and kind to just about everyone he encountered, friends and strangers alike.

But I also saw a candidate who seemed by nature almost uniquely ill-equipped to appeal to the young and minority voters who ended up playing a key role in his electoral demise.

Members of the press who traveled with Romney in 2007 and early 2008 began slowly to pick up on what would become an established media narrative by the time Romney was the 2012 front-runner: The former Massachusetts governor didn’t just have a difficult time relating to young and minority voters, he often came across as a walking-talking time warp from the 1950s.

On the stump, Romney frequently began declarative sentences with the word “why,” and talked about how long he’d been “going steady” with his high school “sweetheart.” And that persona seemed well enough suited to Republican primary electorates, which were disproportionately white and older.

The mostly gray-haired members of his crowds in Iowa, after all, were usually receptive when Romney told of cross-country trip that took him, as a teenager, through the Hawkeye State; he said he’d noticed that the soil was particularly fertile, prompting him to say to himself at the time, “God must love Iowa.”