She's giving him too much credit. He's not all that good at picking up on the nuances of women's vague statements.

'Afraid it's all gettin' a bit personal, Drake?'

He says it like an accusation, swinging through the cold streets like he owns them.

'Jus' thought you needed some cheerin' up.'

That comes out as a mutter, barely audible. And what he might have in mind for cheering her up is unclear.