Why is Olaf chasing the kids, even when Esme is his GF?

[Hermes]

Well, for one thing, he may not want to be dependent on Esme, who is a rather volatile character. For another, as we've discussed elsewhere, his chasing the Baudelaires may be motivated by revenge as well as for his desire for the fortune.

(The bit about Esme being in charge of the Quagmire fortune - which only comes up in TSS - is a bit odd, by the way. You'd never guess that from TEE; the sense we get there is that O only became interested in the Quagmires when they fell into his lap; and he never tries to become their legal guardian, as he does with the B's, but instead has to keep them in secret. Indeed, if his girlfriend controls their fortune, could she not just hand it over, without going to the bother of kidnapping? He has to start conspiracies against the B's because Mr Poe refuses to hand their fortune over. In my fanfic I take the line that while she had been their financial adviser for a while, this had stopped before the main action, because of orphans ceasing to be in.)

[Foxy]

Olaf and Esme's relationship really doesn't make sense to me. Neither of them wants the same things. Olaf wants the Baudelaire fortune. Esme wants the sugar bowl. Esme is already unbelievably wealthy. Count Olaf wants to steal fortunes. And their both completely self-centered, so I don't know why either would want a significant other. And I don't know why Esme would date someone with no personal hygiene. I feel like this is something she would care about.

I wonder if Esme kept it a secret from Olaf that she was in charge of the Quagmire affairs because if he knew she was in charge of them, he would just make her give him their money and wouldn't take her out of the city and on all his... I hesitate to call them adventures. Acts of despicability, I'll call them.