I'd have said that realizing in the first case that you were running your mind and your time was fairly vertebral. What am I missing?
Probably just curiosity at my end, but in the second case, did she turn out to be someone you wanted to spend time with at all?
Not much, it just didn't seem in my opinion as important (though it felt that way at the time), and the backbone growth didn't particularly propagate through my life, apart from ending that whole middle school/high school like-someone-but-never-do-anything-about-it thing.
Short answer, yes.
Long answer, we're good friends now, and its working out much better with a backbone. The main issue with the relationship not working is that a lot of what Robin Hanson speculates about "mating behavior" is true with her (to the point that when I explained those ideas to her she thought I was just being ridiculously insightful and empathetic). Other than that, she's really fun to be around.
We operate like this: the "overseer process" tells the brain, using blunt instruments like chemicals, that we need to find something to eat, somewhere to sleep or someone to mate with. Then the brain follows orders. Unfortunately the orders we receive from the "overseer" are often wrong, even though they were right in the ancestral environment. It seems the easiest way to improve humans isn't to augment their brains - it's to send them better orders, e.g. using drugs. Here's a list of fantasy brain-affecting drugs that I would find useful, even though they don't seem to do anything complicated except affecting "overseer" chemistry:
1) A drug against unrequited love, aka "infatuation" or 'limerence".
2) A drug that makes you become restless and want to exercise.
3) A drug that puts you in the state of random creativity that you normally experience just before falling asleep.
4) A drug that puts you in the optimal PUA "state".
5) A drug that boosts your feeling of curiosity. Must be great for doing math or science.
Anything else?