I've only seen the original Japanese version,
so I have no idea how it's translated to English in the dubbed/subbed versions.
But from the conversation between Tomoko and Gengo when she first appeared,
I can tell she must be his manager in some agency.
When she begun looking for the next possible job for him,
Gengo said "Hey wait, I want to take some break."
And she replied "You are not in the position to ask such.
Mind you, I'm handling an unsuccessful project team, which is not an easy job."
This implies she's in charge of several unprofitable talents like him.
As for Machiko and Shôsaku (the 'hippie guy'),
it's not very clear but I agree with jcollin3k: they are mere friends.
When they introduced themselves to Gengo, they only told their names.
If he was her boyfriend or anything special (such as brother),
it's unnatural that they didn't mention it.
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