Well, he still had to be close enough to hear her.
If there's anyone he shouldn't take his time with, it's Oakley. She's already in the bag. Should he actually go fetch it. Or should she.
While I would say something about both of them not remembering they've met before, it also means she's been in the same kind of trouble before. So their third date seems like it could be predicted...
Or fourth. Maybe more.
Knowing things about a person that way is on one hand rather shallow, but on the other it's something you don't stop learning more about until years into a relationship, maybe decades.