The family friend undoubtedly feels worse because it's a double-betrayal - the friend and your significant other. On the other hand, given human nature, it would be easier to understand. Two people who are friends, who each care about the other, like each other, just happen to be together at the right time, at the right place, under the right circumstances, and voila! Shit happens! Understandable, yes. Excusable, possibly not.
Having said all that though, I think your S.O. fucking more than 5 random people is actually worse. That indicates your relationship has some serious problems or it wouldn't be happening.
The first scenario probably hurts more, but the second is the more serious. At least that's my $0.02 worth.
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When a woman asks for it, is it not the gentlemanly thing to do to give it to her? 
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