I was rewatching 'The Departed' (2006), and I don't know why but for some reason I loved the way Costigan asked Madolyn out!

The first scene that they shared is him attending his therapy session, where it's revealed that Madolyn is his counselor after she's introduced as the woman Matt Damon's character; Sullivan is dating!

Following a heated interaction between the two, Madolyn decides that Costigan would be better suited with a different counselor who isn't her and to her surprise he immediately takes this as an opportunity to ask 'if she'd want to go out with him for some coffee.'

There is something about the way he asked that felt so smooth, makes it look very simple like he's got nothing to lose and viewed it as his one and only chance to take his shot now that he's no longer her patient and would likely never see her again afterwards!

Combining all of that with the look on her face she makes after he asks, where she seems confused but impressed with his confidence was what made me love that moment even more.