The 26-year-old found himself at a crossroads in his career last summer, having returned from Bournemouth after a promising loan spell that ended with yet another injury.
Struggling for fitness and game-time, Wilshere had not represented his country since the excruciating Euro 2016 last-16 exit to Iceland and was staring down the barrel at Arsenal.
"It was an honest conversation," said Wilshere, whose current Arsenal contract expires this summer.
"We have known each other long enough where we can have that relationship where we are honest with each other.
"It was boiling up for a while because everybody knew I had a year left on my deal and I had been out on loan, got injured, and wasn't really in his plans.
"He said, 'I am going to be honest with you and at the moment we are not going to be offering you a contract, so if you can get a contract somewhere else, you can go'.
"Obviously I was not happy with that, but at the same time I was happy he was being honest.
"He gave me the opportunity with three or four weeks left in the transfer window, but I did not find anything that I wanted and at the same time I was not really fit, so I decided that I wanted to stay and build up my fitness.
"He also said at the same time that if I did stay I had an opportunity to fight for my place, and if I performed well in the Carabao Cup and Europa League, I had a chance."
It was a difficult conversation to digest, but Wilshere is used to setbacks and decided to fight on.
The 26-year-old stayed at the Emirates Stadium and knuckled down, with cup competitions giving him a platform to prove his worth - and fitness - to Wenger.
So impressive has Wilshere been that talks are under way over a new deal, although there have been mixed messages coming from midfielder and manager as to where negotiations currently stand.
Asked if he would like his club future sorted before England go away, Wilshere said: "I have got three months left on my contract. I don't know how to answer that.
"Ideally, yes, I want it sorted as soon as possible.
"I want to go to the World Cup and enjoy it, but we have three months till then and a lot can happen.
"Ideally from my point of view and the club's point of view, they will probably want it sorted."
Wilshere claimed it would not be a distraction if it remained unresolved heading into the World Cup, while he "would not say no" to a move abroad if he leaves Arsenal.
That is not a scenario he claims to have really contemplated, though, as he is focused on "probably one of the most important years of my career".
The World Cup is a major target and Wilshere now has the chance to "stake my claim" in Friday's trip to Holland.
"It's completely different," Wilshere said of the squad make-up compared to when he made his senior debut in August 2010.
"I remember the first time I walked into an England squad, I went for dinner the first time and there was (Wayne) Rooney, (Frank) Lampard, (Steven) Gerrard, (Rio) Ferdinand, (John) Terry - big players who I had watched growing up.
"It's a different feel now. There's more young players, there's more of a group I think and there's more of a plan towards the future.
"The World Cup is a massive thing for us and we want to do well."
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