And it led to a brilliantly awkward moment on Drivetime, as the former striker was caught like a rabbit in headlights live on air.
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The pair had formed a formidable partnership at the Stadium of Light during the first half of the 2010/11 season.
Sunderland forked out £13million on Ghana legend Gyan from Rennes following his impressive displays at the World Cup in South Africa.
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And he repaid the Black Cats' faith by scoring ten Premier League goals in his opening campaign.
At the time of Bent's departure to Villa, Gyan had banged in seven top-flight goals, with the ex-England international firing in eight goals.
The Wearside outfit were also sixth in the table, but ultimately finished that campaign back in tenth without Bent's goals, after he decided to up sticks and move to Aston Villa in January.
And Gyan, who eventually left in the next transfer window to United Arab Emirates outfit Al Ain, still remains hurt over the timing of Bent's exit.
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And, for once, the former striker was lost for words!
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Appearing on Drive, talkSPORT host Andy Goldstein told Gyan he had two more questions for him towards the end of the interview where he wanted a one-word response, but not before the ex-Udinese ace delivered a question of his own.
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Gyan asked Bent: "I want to ask Darren why he left Sunderland."
To which Bent sheepishly joked: "Have we still got time? Is it break time? Have we got a break?"
Pushed by Goldstein to give an answer, Bent remarked: "At the time Asamoah, it was just one of those things.
"Listen I knew it was your time to shine, so I thought if I don't move over, you're going to take my spot anyway, so the platform was yours."
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Not having his reason, Gyan replied: "I know, I know Darren, but we were playing good.
"We were comfortable playing two strikers, honestly, I was disappointed.
"Because we got to know each other, and we were performing, and all of a sudden you left."
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Understanding his hurt, Bent said: "Yeah I know, it was one of them decisions where I still look back and think, 'hmm'.
"No, listen, at the end of the day we got to spend a little bit of time together, I enjoyed our time together… and Andy please hurry up and ask Asamoah those two questions!"
One of the breakout stars from the 2010 World Cup, Gyan famously missed a dramatic last-minute penalty against Uruguay which would have sent the African nation through to the semi-finals.
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Luis Suarez had handled a shot on the goal-line to give Gyan the chance to score in extra-time, but he blazed his effort over the bar,
Ghana subsequently lost the shootout, but Gyan told talkSPORT he holds no grudge against Suarez after insisting he'd have done the same thing in his situation.