Because I feel adventurous, let's see if I can expand the actual answer of, "When he asks you" into 300 words. Are you ready? Grrrrrrrrrrrrrrrrrrrrrreat.

So my guess is pretty much when he comes up to you and says, hey, do you want to go out, unless of course there's a much prettier girl standing behind you in which case he's not asking you but her, which would TOTALLY blow, but hey you live you learn ya know, kind of like that song by Joe Public, except their song was called, "Live and Learn" but the concept is the same if you think about it, then again if you were thinking you'd realize the answer to this question as opposed to writing into some seemingly racially ambiguous Black guy (you see what I did there) with a random white chick over his shoulder who is either whispering sweet nothings in to his ear or really needs to go potty, neither of which is clear just from looking at the picture, which I guess refutes the notion that a picture is worth a thousand words if nobody can muster more than, say 100, out of that one since lke I said, its confusing, befuddling, or downright confuddling which I'm pretty sure was the last name of the 6th Beatle who got kicked out of the group for answering every question with a question since that gets MAD annoying after the third or fourth time since nobody wants to be questioned all of the time about anything, especially not chord progressions so I'm guessing McCartney gave him the boot unlike his wife who he tried to boot but now she's stuck her foot so far up his fanny that every time he speaks to her it costs him money, I guess he lived and learned, which takes us back to the original question and answer, which is, indubitably, when he asks you.

And yep, that was about 300.