To me, it's almost like CBJ is that average-looking, slightly pudgy girl you took to prom, while Gruden is that smoking hot rich girl that you could have taken if you hadn't accidentally thrown up on her when you tried to ask. And then after the fact telling yourself that she probably wasn't even interested, and you didn't really want to drive her dad's Porsche there, and that she probably wouldn't have put out, anyway.
And who knows, maybe pudgy girl will let you round the bases, maybe she even pleasantly surprises you in some ways you never even expected.
But you'll always wonder how things might have turned out with that smoking hot girl....