Beto O’Rourke’s headed to Iowa this weekend. He just made the rounds at the South by Southwest (SXSW) festival in Austin. He's stayed in the headlines with creative, at times unusual, gimmicks like live-streaming his dental appointment and posting soulful blogs from the road.

And ahead of his trip to the state that votes first in the presidential caucus calendar, O’Rourke has launched over 300 Facebook ads touting that he’s made his 2020 decision: "People in communities across the country have been reaching out and asking me if I'm planning on running in 2020. I have made a decision on that. Sign up today to be first to know what's next. I'd like for you to be a part of it."

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But amid rampant speculation that the former congressman from Texas turned rock star in the eyes of many Democrats is preparing to launch a White House run is concern that the waiting game is taking its toll on his unique brand. As the deadline for O’Rourke to first make a decision and now announce that decision keeps slipping, it’s led some party pundits to wonder whether the candidate who nearly ousted conservative GOP Sen. Ted Cruz last November may have missed his moment to capture the Democratic nomination.

Timing is everything in politics – think then-Sen. Barack Obama catching lightning in a bottle as he captured the Democratic presidential nomination and eventually the White House in the 2008 election cycle.

Should O’Rourke have jumped into the race in December or January, when ‘Beto mania’ was at a fever pitch?

“I do think that Beto O’Rourke’s star was much stronger a few months ago and the polls indicate that every week that goes by, that he plays this game, he drops even further,” said a longtime Democratic consultant, who asked for anonymity to speak more freely.

But veteran Democratic strategist Jesse Ferguson strongly disagrees.

“He may win or lose the primary, but it's hard to see any primary voter in winter 2020 voting against him because they held a grudge that he spent too long thinking in winter 2019,” argued Ferguson, who served as a senior spokesman on the 2016 Hillary Clinton presidential campaign but remains neutral this cycle.

“As we watch Trump announce things that don't exist and irrationally react to conspiracy theories, voters won't resent someone who takes the time to be sure about a decision. Being thoughtful isn't a vice, being rash and irrational is,” he emphasized.

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Another strategist was more blunt.

“Anyone claiming it's too late for candidates to jump into the race either has an agenda or is just plain stupid,” said the strategist, who also asked to remain anonymous to speak more freely.

Still, the drawn-out pre-announcement period has allowed other big names to dominate the conversation, including numerous high-profile senators who have already declared candidacies as well as former Vice President Joe Biden -- who also has not announced his decision but is polling much better than O'Rourke at this early stage.

O'Rourke's trajectory from here is anyone's guess.

The three-term congressman from El Paso first rose to national attention last summer and autumn, as he challenged Cruz in the 2018 midterm elections. O’Rourke raked in an eye-popping $80 million during his campaign, thanks in part to his uplifting message and his mastery of social media.

He immediately became a Democratic rock star. And like Sen. Bernie Sanders of Vermont, another darling of the party’s progressive base, O’Rourke quickly reached celebrity status, being referenced only by his first name.

O’Rourke narrowly lost to Cruz -- by just over 200,000 votes out of more than 8 million cast. After his better-than-expected performance against the GOP incumbent, there were immediate calls by some Democrats for O’Rourke to run for president.

After saying days after the November elections that "I will not be a candidate for president in 2020,” O’Rourke quickly changed his tune, explaining that "I haven't made any decisions about anything yet.”

By mid-December, he acknowledged at a town hall that he was considering a White House run.

In early January, with Beto mania heating up, O’Rourke live-streamed a visit to his dentist, which while going viral was also greeted with plenty of derision on social media.

Days later, as the Democratic presidential contenders were busy building organizations and making frequent stops in the early voting states, O’Rourke tried to find clarity. So he embarked on a solo road trip across the country, posting rambling dispatches on Medium.

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That trip came under attack from New York Times reporter Lisa Lerer, who argued that no female politician could get away with O’Rourke’s style of exploring a presidential campaign bid.

“Imagine, they say, if Beto were Betsy,” Lerer wrote in the Times. “What would the reception have been if a female candidate left her three small children home and spent several weeks traveling the country, posting stream-of-consciousness diary entries? Or if she chose to forgo a Senate race that would provide a greater opportunity for victory?”

O’Rourke, in a much-anticipated early February interview with Oprah Winfrey, said he’d make a 2020 decision “really soon … before the end of this month.”

But that deadline came and went.

Two weeks ago came word that O’Rourke had ruled out a 2020 Senate challenge against Sen. John Cornyn of Texas and would announce his decision on a presidential bid “soon.”

O'Rourke then told reporters that he had made a decision, but remained mum on what he had decided.

"I want to make the announcement to everyone at the same time," O'Rourke explained. "I want to do it the right way."

This past weekend, the apparent O’Rourke tease continued, as he attended South by Southwest for the premiere of a documentary about his 2018 Senate campaign.

He avoided revealing or detailing his 2020 intentions.

“I want to make sure I do it the right way and I tell everyone at the same time, so I’ll be doing that,” he once again told reporters when questioned about the delay in any announcement. “I’ve got to be on the timeline that works for my family and for the country.”

On Monday night, a video from O’Rourke on Twitter indicated that he would head this upcoming weekend to Iowa to lend a hand to a Democratic state Senate candidate running in a special election. The news came as O’Rourke reportedly had started staffing up in the Hawkeye State.

A new national poll from Monmouth University, meanwhile, indicated a slight deterioration in his popularity. O’Rourke enjoyed a 41 percent-9 percent favorable/unfavorable rating in January. Monmouth’s latest survey, released on Monday, showed O’Rourke with a 38 percent-12 percent favorable/unfavorable rating.

The longtime consultant critical of his approach argued that by waiting, O’Rourke is “just going to be one more candidate because he didn’t strike when he was hot.”

But others point to a lack of a breakout candidate so far in the large field of Democratic presidential contenders. They argue that a campaign launch by O’Rourke could shake things up.

A consultant who spoke anonymously pointed to Biden and Sen. Bernie Sanders of Vermont topping the Democratic nomination polls, arguing that “the primary is a complete free-for-all with the two so-called frontrunners artificially inflated by name ID and the fact that their records have yet to be vetted. No one has any idea which candidate is going to ultimately connect with early state voters until they're well into doing it.”