Alex really does have an abnormal amount of power in all aspects of her life if you think about it. She basically has the run of a library that she, essentially, owns. She’s paid mostly by a trust set up by her great… great… (I’m not sure how many greats) grandfather, and pretty much makes her own rules. I’m sure that accounts for a lot of why she’s generally happy all the time. It’s often said that you can’t buy happiness, but it has remarkable abilities when it comes to removing worry from your life. Which is an approximation of happiness at the very least.
Of course Reggie’s family has money, but they don’t allow him to do with it what he will, not that having access to said money would make Reggie happy deep down. Superficially he might be happy, but since he lacks the wisdom to make it stick long term simply by having wealth. That emotional maturity is what a lot of rich, successful people lack, which I why they stay miserable in spite of success. It’s not one specific thing that can give you that wisdom. Everyone has to work it out for themselves, and some never will.
Honestly, I’m not an expert when it comes to happiness, because I certainly don’t have the secret of it. I can see it in others, but I’m not sure what specific things I need to do to get there myself. Of course it might all just boil down to brain chemistry and everything I’ve posed at the beginning is just smart sounding bullshit. In fact, I think there’s a pretty good chance that’s the truth of a lot of what I say.
In any event Reggie has a shaky sense of self worth. On the one hand he believes he’s great, but somewhere inside he doesn’t believe it, so he has to try and force other people to repeat his hope back at him. Of course he’s gotten better over time, but he’s not quite there. He’s harsh, blunt, and mean spirited, but he also has standards, and wants to do good as he understands good to be.
Most of the cast is like this to one degree or another. They have flaws, but want to do good in the world.