How Close Do You Have To Be With Someone To Ask Them For Money?

So we're all familiar with the "three feet of personal space" we need to maintain sanity.  For some of us, that distance may be a little farther or, in the case of your ex, a restraining order.

But something happened the other day that sparked a discussion here at the office - Kendra Wolfe received a financial request from a college grad who owes $90,000 in student loans and hopes to get married next year.

I will say, it's not the worst request I've heard - as 1) it seems to be for good reasons (i.e. not drugs and booze, assuming he's being honest), and 2) as a music school grad, music/audio schools do a TERRIBLE job of giving you an accurate post-college picture of life.

Nonetheless, this led us to ask: what's the "personal space" rule with money?  Or in other words, how close do you have to be with someone to ask them for money (with a good conscience)?