Would the England winger benefit from a change of scenery after what has been a frustrating season at the Emirates?
And the forward may have to contemplate the very real possibility that leaving North London might be the best option for his career.
Now, make no mistake, that's not to say Walcott should leave the Gunners, a side he has been with since 2006, it's merely saying that he can't afford another season like he's had this year, where he has played a bit-part role in the first team.
The 2014-15 season has been far from ideal for Walcott. He didn't fully recover from the cruciate ligament injury that forced him to miss the World Cup until October, with the winger making his first squad appearance against Burnley at the end of that month when he was an unused substitute on the Arsenal bench.
A groin strain ruled him out of several further games at the end of November and beginning of December, but however much Arsene Wenger was eager to keep his player from damaging himself once again, the hard fact is that since appearing as a substitute against Liverpool at the end of December, Walcott has spent over four months on the Arsenal bench, and even more alarmingly for the former Saint, he hasn't really been missed.
Wenger's men have put together a superb run since the turn of the year to push themselves to within a point of second position in the Premier League, with it looking increasingly likely that a top four finish is the very minimum they should be aiming for.
And with the Gunners winning their last six games, has the Frenchman found a style of play and lineup that best suits his philosophy?
Since returning from that groin strain, Walcott has been on at least the bench in each of the 14 Premier League games he has been available for. The problem is, he has started just three of those matches and found himself an unused substitute 8 times. If he was being honest, he would have to admit to being lucky to be selected by Roy Hodgson for England, considering his lack of playing time. Despite that loyalty from the England boss, Walcott has slipped from his country's starting lineup.
With the injury Alex Oxlade-Chamberlain suffered in the FA Cup win over Manchester United, Walcott may have fancied a renewed role in Arsenal's first team, but he has only started one of the three games since Old Trafford, and was crucially on the bench as the Gunners sought to overturn the 3-1 deficit to Monaco in the Champions League. The role he played in Aaron Ramsey's second goal proved that he had something to offer in that match, and there is no doubt that the England international is far from being a spent force, but the form and presence of the likes of Chamberlain, Mesut Ozil, and the new arrivals of Alexis Sanchez and Danny Welbeck make Walcott's right wing position a highly competitive one.
Walcott is certainly a strong enough player to make an impact at any of the other elite clubs in the Premier League, with Jamie Carragher already admitting that Liverpool have looked at him in the past, while his dwindling contract will mean Walcott can talk to foreign clubs as soon as next January.
There would undoubtedly be plenty of interest from European clubs, while his previous hopes on wishing to play in a more traditional striking role could also be fulfilled elsewhere, given the impressive form he showed in the 2012-13 season.
But maybe all Walcott needs is a full pre-season under his belt, before reclaiming a regular role in Arsenal's starting lineup and signing on at the club for life.
At least that is what he will have to tell himself if he is to consider extending his Emirates contract, because the speedster will unlikely be satisfied as an impact substitute during what should be his peak years as a footballer. Ultimately he has to ask himself, how long am I prepared to wait for my chance?