Whether they're appearing at some book signing, endorsement opportunity, charitable function or on their way to rest room, the question isn't far behind.
As long as this cloud of uncertainty hovers, the question will linger until there's finally a resolution.
The question was foisted on LeBron James during a promotional stop in London, England.
Dwyane Wade was asked during a visit to his native Chicago.
And, no doubt, Chris Bosh will get it next Friday when the Raptors are scheduled to convene at their annual golf tournament to support the club's charitable foundation.
Will they or won't they?
Will each decide to stick around with their respective teams beyond this coming season or will each exercise their negotiated right to explore free agency next summer?
James, Bosh and Wade each came into the NBA in 2003.
Bosh and Wade each followed James' lead when King James took less term on a new contract.
Each has been very astute when questions of their future get broached.
No one has yet to blink and no one even remotely associated with basketball believes any will sign an extension, meaning each will test the free-agent waters.
If Wade is to leave South Beach, would he list Chicago as his preferred destination?
"If I disclose that kind of information, the articles this season aren't as exciting anymore," Wade said.
The Heat overachieved last season because of Wade.
The team hasn't added a significant piece this off-season and has cut costs, at least when it comes to officials not capable of hitting perimeter jumpers or getting the ball into Wade's hands during games.
Wade has said all the right things and is hopeful of staying put.
With Jermaine O'Neal's $23-million US contract coming off the books next summer, the Heat will have cap room to pursue a big-time free agent to ride shotgun with Wade, assuming Wade commits to Miami.
Money won't be issue, whether it applies to Wade, James or Bosh.
The key is winning.
Wade has a leg up on his celebrated draft classmates because he helped lead Miami to an NBA title.
James has come close and figures to be knocking on the door this season.
As for Bosh, the Raptors are better but are far from being championship contenders.
Of the three teams, the Raptors are better positioned to move forward if their "franchise player" decides to bolt.
It's not even close.
If James were to leave Cleveland for, say the bright lights of New York, the Cavs will have to start from basically scratch because the players they've lined up long term can only excel with James on the floor.
The painful remnants of a Heat team minus Wade was evident when Miami tried to defend its 2006 crown.
Without Wade, the Heat won 15 games.
The Raptors are better with Bosh, but they are not as vulnerable when compared to Miami and Cleveland.
If Bosh is forced to miss any games for whatever reason, Andrea Bargnani can slide into his natural position at power forward.
There's a late-game creator and scorer in Hedo Turkoglu, who will have the ball in his hands late in the shot clock, or at least he should have the ball in such scenarios.
Miami is reliant on Wade just as much as Cleveland relies on James.
The Raptors don't have to lean on Bosh and the team doesn't need the daily reminders of Bosh's future, which may become a distraction.
That is why the Raptors can afford to trade Bosh.
The question remains: What can the Raptors get back?
Moving Bosh might be the team's only option to rid itself of Marcus Banks and perhaps acquire a bona fide centre who will defend the post and block shots.
It's a move worth exploring.