Re: Obi-Wan Kenobi
Oh, Yelena's buying them shots to make sure he gets on stage before the night is over. She might even do some of it it with his money if she can pickpocket his wallet and get it back there without him noticing just because being a regular human and asking to split the tab is never actually going to occur to her.
And if he doesn't want to do Madonna alone, she'll totally turn it into a duet with him. She might even if he's willing to do Madonna alone!