Despite the warm weather, Cheryl wrapped up for her dinner date at swanky Mayfair restaurant Scotts, arriving in a slouchy knitted jumper, a loose leather skirt and matching statement heels.
No sooner had she arrived, than the songstress took to Twitter, tweeting snaps of herself and her superstar manager, with the caption: 'Fancy seeing you around here @iamwill #majah.'
We're not sure if Cheryl actually did bump into Will at the posh haunt, or if the dinner had been in the diary for ages. Either way, the pair seemed to be having a lovely time.
Earlier in the evening, cheeky Cheryl Cole sent a message of congratulations to 18-year-old diver Tom Daley on his bronze medal win - and asked him again for a diving lesson.
The smitten starlet wrote: 'Congratulations @TomDaley1994.. You did us all proud.. !! Now you should have some free time to teach me that dive !! :D.'
And just seconds later, Tom Daley wrote back, teasing: 'I will :) we need to get it organised! I will DM you now :).'
Cheryl first kicked the flirt-athon off last week when she Tweeted Tom Daley, writing: ‘@tomdaley1994 I think you are amazing! Will you teach me how to swan dive?’
The request was somewhat tongue in cheek following Cheryl Cole’s surprise swan dive off the stage when she performed on BBC1 talent show, The Voice UK earlier this year.
But it seems Cheryl might just be getting that diving lesson after all...
Will Cheryl Cole bag herself a private dive with medal winner Tom Daley? Let us know in the comments box below…