Well, he is working a job though, isn't he? Sleeping with ugly old men for money. So in that case, I'm definitely laughing at him, as are most people.
And there's the thing with Dylan - he's so tacky that he can't help but show off. So if he did have any higher connections he absolutely would've found a way to try and show off about them.
The other aspect is that he's always going to be marked with this. I've seen some say he still wants to be a lawyer. Christ, can you imagine the senior partner's faces when they see the background research on Dylan? And most of it put online by Dylan himself - another example of his extremely short-term thinking.