Nearly three decades ago, Mitt Romney left his office on a Friday afternoon, gathered his wife and kids in the family station wagon and drove out to spend the weekend at the Rhode Island beach house of Patrick Graham, a founding partner at Bain and Co.

Romney pulled into the driveway, jumped out of the car and immediately ran over to Graham’s Doberman pinscher, Samurai. Clad in a suit and tie, and eager to set a rollicking tone for the weekend, Romney grabbed Samurai’s favorite rubber ball from his mouth, led him racing down a sandy path to the beach and launched the ball into the water.

“Well, the damn ball didn’t float,” Graham said. “And my dog Samurai, he dove into that ocean for hours, and he’d come out of the ocean just whimpering.”

Romney, too, looked as though he might cry.

“I never saw Mitt feel so bad,” Graham said.

Sometimes Mitt Romney overdoes it.

In politics, his well-noted desire to please has led to “Saturday Night Live” skits and a whiplash-inducing record of political positions. On the campaign trail, Romney has uttered memorably pained locutions — such as telling people in Mississippi that he’d eaten “cheesy grits” — and once sang “America the Beautiful” at a rally in Florida. His efforts to relate to voters who have little in common with his wealth and religious background have left him at times looking forced and stiff.

The people who know Romney well, and who alternately describe him as a barrel of laughs and a master persuader, can’t figure it out.

“I worry about him,” said Clayton Christensen, a fellow Mormon, an influential business theorist and a friend of Romney’s.

In his office at Harvard Business School, surrounded by certificates and the books he has written — including “The Innovator’s Solution,” “The Innovator’s Prescription” and “The Innovator’s Dilemma” — Christensen argued that Romney should open up more. He said the candidate should talk about the way he navigated acrimonious negotiations between the selling partners and the junior partners at Bain and Co. during a near-mutiny that nearly sank the firm.

“Oh my gosh, if you could tell that story in the context of a bifurcated Congress that can’t agree on anything,” Christensen said, adding that there were “hundreds and hundreds of people whose livelihoods depended on this. Why can’t he tell us this story? Nobody knows.”

Christensen said he has appealed to Romney to reveal more about his life, especially “in the context of the church,” but he hasn’t gotten anywhere. “Mitt doesn’t have an instinct to be open in his personal life,” Christensen concluded.

The Romney campaign has tried to loosen him up. His advisers have leaned on his likable wife, Ann, to supply humanizing details (she told Parade magazine that “he’s a big cereal hound”) and his personal assistant to bring him down to Earth (“He always goes, ‘What’s up, boss?’ or ‘What’s up, doc?,’ ” the aide told the New York Times).

They have put the candidate in more relaxed settings to bring out his affable side. In December, he appeared on David Letterman’s show to read a Top Ten list of “Things Mitt Romney Would Like to Say to the American People.” (No. 9: “What’s up, gangstas? It’s the M-I-Double-Tizzle.”) Asked by Jay Leno in March to associate words with political personalities, he acquitted himself well, saying “huge” for Donald Trump and “press secretary” for Rick Santorum.

Some observers have noted that Romney avoids telling some of his most flattering personal stories — saving dogs instead of sinking their toys or transporting them atop station wagons; organizing a search party for the daughter of a Bain colleague — because they brush up against the enormous wealth and Mormon faith that he is clearly uneasy discussing.

Whatever the reason, his wariness of saying the wrong thing or fumbling a line on the trail has often made Romney look like a man on a tightrope. When he blew an applause line during his Super Tuesday victory speech in Boston, his knees buckled and he rocked back in exasperation.

For people familiar with him outside of politics, candidate Romney is hard to reconcile with the man they once knew.

As a kid in Michigan, Sidney Barthwell Jr., a high school classmate, recalled Romney as a prankster driving doughnuts in snowy parking lots. At Stanford, he lured rival University of California students into a trap in which his buddies “shaved their heads and painted them red,” according to a 1970 speech at Brigham Young University by his father, George Romney. George Keele, who served his mission with Romney in France, recalled Romney’s talent for teaching through example and without piety, as well as his ability to laugh.

One night in Bayonne, in southern France, Keele answered a knock on the door and saw two men, their faces hidden by sheets, ordering him in French to put his hands behind his back, turn around and not utter a word. Keele fled out the back door only to hear Romney, his mask removed, laughing uproariously in the house.

“George Romney was gregarious — Mitt Romney is probably three times as gregarious as his dad,” said Keele, who said that Romney resisted urging Ann to convert to Mormonism because he “has always been someone who doesn’t use his eminent powers of persuasion to wield unrighteous dominion.”

Like many people who knew Romney in the past, Keele has a hard time recognizing the candidate on the trail.

“Mitt Romney is capable of relaxing,” he said. “The stiffness that people see is simply Mitt trying too hard.”

Ultimately, Christensen thinks Romney is trapped in a sort of Catch-22. He is clearly at pains trying to relate to an electorate that does not share his wealth or upbringing, but voters seem unwilling to let Romney be the wealthy, devout, model family man that his supporters describe.

“I think our inclination is that we see somebody who is playing at a different level: ‘They can’t be real. They are not like me,’ ” Christensen said. “It just hurts because you have this real guy.”