crush on the older, cool girl as an awkward young fellow and then, later, how much was a workaholic wanting to love someone but not wanting the details of a relationship to get in the way of the work

I think a lot of people have the issue of wanting to love someone who is unattainable--for a whole lot of reasons. I've noticed how people will do that and will pursue someone relentlessly until they cave in and then there is frantic backpedaling.