This actually speaks a lot to Neal's character, I think. Considering he's a white-collar criminal who's accustomed to luxurious living, you'd think money would be something important to him, but it's a "prop." It's the life that he likes, not the means to achieving it. And associating "hope" with "women" does two things: 1) establishes him as a more respectful/respectable character than James Bond (haha), and 2) takes you all the way back to Kate. He never really did give up on her.
This scene was so sad I was crying and then kate got blew up in the plane so j started celebrating and laughing for a second cuz I hate Kate and then I saw Neal I paused it when he was like flying though the air with the explosion behind him and then I started crying again