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It's a tough call, really. I've personally guaranteed several loans in the past - for a couple of employees and two friends. One person was flipping houses and the other guy had medical issues. I don't have a philosophical problem with it even though I once had to take up some slack for a buddy who fell behind. Sometimes people need a little assistance and, when I'm not insulting people for grins, I don't mind helping if the circumstances are right.
Having said that, I would have to know the person pretty damn well. It would be extremely uncomfortable, for example, to discuss co-signing a note for a girl I just started dating. I mean, if you decline, I'm pretty sure the relationship would be over. I can hear it now; "You don't trust me?". Oh, my God. Then, on the other hand, it could well turn out to be the most expensive sex you ever had. Those aren't particularly good options unless it's Gillian or Salma or somebody.
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