Drinking with the characters is dependant upon your personality class...
Teammates like the Team Captian
Managers like the Self Promoter
No one really likes the Perfectionist (but i think this puts gains into auto-pilot)
The Pragmatist falls somewhere in between
In anycase Charisma impacts interactions a great deal as well.
I usually get the guy down to 3-4 drinking bars and then ask him. I have never played as the self-promoter/Barry Bonds type and I have NEVER gotten money from the GM. Don't know if it is just a small sample size though.
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