Newt Gingrich returned to his old stomping grounds Thursday to meet with House Republican freshmen. The former speaker who led the 1995 federal government shutdown was counseling the Capitol Hill rookies, but it’s clear he also wants to woo them as he gets ready to announce his presidential exploratory committee.

“The campaign before the campaign” has been a rocky one for Gingrich. Although he’s been out of office since 1998, he's remained in the public eye as a contributor for Fox News and with book deals and movie projects. Now his nascent campaign seems to be stumbling: He gave numerous conflicting answers on Libya; has had trouble answering the questions he knew were coming about his personal life; there was confusion about whether he was announcing an exploratory bid or not, as well as several eyebrow-raising comments. And this is all before actually getting into what is sure to be a bruising race with a crowded field.

A reporter after the meeting asked Gingrich if he was content with how things were going. Gingrich replied, “I’m perfectly happy.” Asked if they would take back any of the moves made up to now, a top aide said, “No.”

Will a stumble out of the gate hurt Gingrich’s campaign or is too early to even matter to voters? And shouldn’t the most seasoned politician in the race have his talking points prepared? Analysts, observers, and those who know him say that’s just Newt… but will that work in the early states? Alan Abramowitz, a political science professor at Emory University, says there are concerns about his electability even in his home state of Georgia because of his “personal history” and “comments that can come across as overly harsh or extreme or hypocritical in some cases.”

“He’s never run for anything outside his one congressional district... He really has no experience running a national or even a statewide political campaign or appealing to a broader electorate. I think it’s mainly his personality, that’s just Newt,” Abramowitz said. “He’s just irrepressible. He’s always got new ideas, energetic... but he has a huge ego [and] he just sort of barges ahead.”

“For him to almost be victimized by the 24-hour news cycle and the way people are able to research things and say things is kind of incongruous with what he used to say and sort of be.”

Gingrich’s changing positions on Libya have been widely skewered. He called for a no-fly zone in early March, then reversed that position a few weeks later, saying he wouldn’t have intervened—and then he quickly reversed again, saying Col. Muammar Gaddafi should be defeated. In Iowa last weekend, he admitted to “contradictions” in his statements, but spokesman Rick Tyler explained Gingrich was merely responding to the president’s “shifting positions and confusing signals.”

“I think Newt has said the same thing all along and I’m very confused why the press can’t see the difference between Col. Gaddafi has to go and Gaddafi can you please kind of go because this is really making me look bad,” said Tyler, referring to what he perceives as President Obama's shifting sentiments.

David Woodard, a GOP strategist in South Carolina and professor at Clemson University, has known Gingrich since the early 1990s. When Woodard was campaign manager for then-House candidate Lindsey Graham in 1994, Gingrich headed up GOPAC and they would have weekly conference calls with candidates and staffers around the country. Woodard said Gingrich—famous for his wonkiness— was exceptionally good with messaging, stressing word choices that could work on both voters and the press. It makes Woodard wonder why Gingrich is now struggling on, of all things, messaging.

“The thing they don’t expect from Newt Gingrich is waffling like that, because he made his reputation by being very declarative about what he believed and why. If there is one thing that characterizes his whole career, it's that he’s been articulate on the issues and good at explaining them in soundbite ways,” Woodard said. “It doesn’t seem characteristic for him to be on one side of the issue and then another. It’s just not in keeping with his whole political career.”

The other issue looming: his personal life. Gingrich has been married three times and admitted to extramarital affairs, including one with the woman he is now married to, which came at the same time he was blasting President Clinton over the Monica Lewinsky scandal.

“Three wives is a hard thing to explain,” Woodard said. “I think there are still a lot of people in the Republican Party who are very active politically because they care about social issues especially the traditional issues like marriage. It’s hard to see how Newt Gingrich would be the embodiment of traditional marriage given some of his life experiences.”

Woodard says he was with Gingrich in a van from the airport to Clemson when the scandal first broke in 1998. He said “sharks were swimming in that bus that day,” describing the Republicans salivating over the incoming news, but Gingrich remained very quiet.

“I thought at the time he was thinking through the implications before he wanted to comment on it. I realize now there were other reasons,” Woodard recalled.

One top Gingrich aide admits his past is “a concern,” but says voters are more focused on job creation, energy policy, and health-care costs. “I haven’t had any voters ask him about it,” the aide said. “The only people that seem to truly care about it is the press, but when the press asks, he answers in a forthright, honest and in a way that takes an enormous amount of courage.”

Woodard says he believes the early missteps are because of the new media world that Gingrich is now facing. Despite being at the forefront of technology while in office—Woodard said Gingrich advised campaign managers to fax every local media outlet and “keep blasting the message”—he’s now stumbling under the constant scrutiny.

“Now you have bloggers and the press… right on top of things almost instantaneously and you don’t have time to sort of be reflective or to sort of recycle the message or correct it,” Woodard said. “For him to almost be victimized by the 24-hour news cycle and the way people are able to research things and say things is kind of incongruous with what he used to say and sort of be.”

The Gingrich aide disagrees, stressing that “we’ve adapted just like everybody else. We have iPads now, BlackBerries, we have iPhones. We communicate through Facebook and Twitter. Newt has 1.4 million people on Twitter, which is more people following him on Twitter than watching MSNBC at any given moment of the day, so we are fine.”

With wife Callista by his side and his conversion to Catholicism two years ago, he has reinvented himself and will use these changes to try and woo social conservatives, but he has clearly been tripped up when asked about his past. He told the Christian Broadcasting Network that his infidelity was “driven by how passionately I felt about this country” and that he worked “far too hard,” but that didn’t get received well either. Chris Wallace on Fox News Sunday said many people thought the answer was “kind of lame.” Gingrich said he decided to pursue Clinton’s impeachment despite engaging in an extramarital affair himself because he believed the president was committing perjury, telling Wallace, “I don’t know what you would have had me do.”

Will the excuses work? Craig Robinson, former political director of the Republican Party of Iowa, says Gingrich’s past “will matter in Iowa to some Iowans, not all.”

“I think he missed an opportunity [with the CBN interview] and his reasoning kind of didn’t sit right with those of us paying attention. You hear it and you’re like: Really?” Robinson, who is going to remain unaffiliated, said. “When people are going to question you on a personal matter it’s harder to address as a candidate. It’s not like you can show up at an event tomorrow and start your speech by talking about your personal life and shortcomings where if your problem is policy-based… you can actually address those in a comfortable manner when you campaign, but your personal failings are more difficult.”

And Iowa and New Hampshire voters are notorious for asking tough questions.

“In Iowa and New Hampshire it’s very, very difficult to be a hypocrite or even to be perceived as a hypocrite,” said Patrick Griffin, GOP consultant and fellow at the New Hampshire Institute of Politics. “He’s a smart guy. He clearly knew this is coming, knows this is coming, knows this is an issue and is going to continue to be an issue until voters believe he is a serious candidate who can address the perceived hypocrisy issue—which, fairly or unfairly, that is what it is with the speaker.”

Griffin said Gingrich has been getting crowds in New Hampshire. “There is a curiosity factor around Newt Gingrich which is somewhat unstoppable at least for right now. Does that translate to votes in New Hampshire? I’m not sure anyone can answer that. It’s going to require more than just Newt being Newt for that to happen.”

Despite problems with his candidacy, at 67 years old this might be Gingrich’s last chance to go after the White House.

“If he doesn’t do it now, he won’t do it. This is his chance. He’s getting kind of old. I think this is his opportunity,” Woodard said.

Shushannah Walshe covers politics for The Daily Beast. She is the co-author of Sarah From Alaska: The Sudden Rise and Brutal Education of a New Conservative Superstar. She was a reporter and producer at the Fox News Channel from August 2001 until the end of the 2008 presidential campaign.