I was doing sound and asked the bassist if I could play his bass. He said yes, it was an Alembic 

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I should probably just start a new thread. Please accept my apologies for the highjack, but after 12 pages, I think we understand that “some people are cool with it and some are not.”
Anyway, here’s a funny twist to this scenario.
A local politician is having a fundraiser with a legendary blues guitarist (I will not name), my boss was “invited” to the function. To which he replied, “...Only if my guy Matthew can sit in with xxx”
I was mortified and tried to explain to my boss that it is not polite or cool to ask to sit in.
The local politician replied that he would “make it happen”
So, WHAT THE #%#% DO I DO?
I haven’t made it this far in my career saying NO to my boss or being timid. But, I’m not a jerk that “asks to sit in” either.
PS: if the “legendary blues guitarist’s” bass player happens to read this... please let me know how you feel. I can fake an illness or something to get out of this.
Thanks, but that’d be too obvious.show up at work with a finger bandaged