Would you let your 16 year old daughter go on a one week trip with a 40 year old male friend of yours, both alone together on this vacation?
As the father of two daughters (ages 11 and 14), I can tell you with absolute certainty that you've just asked the dumbest question in the history of the universe.
+1 i'll add that, if my 'friend' were to even ask me this, he might just end up eating his teeth.. and definitely would not be my friend any longer.
Probably a little. No offense, but as has already been pointed out. This is an incredibly stupid question/something to consider letting your young daughter do. Unless maybe you care more about your friend than your daughter.
Of course the normal, common sense answer to the OP would be no to letting a "friend" take out your daughter. If the so-called friend had the gall to ask, then he wasn't a friend to begin with. It's like the unspoken rule where friends don't flirt with another friend's wife. Or back in high school, friends don't date your ex-girlfriend.