I guess I have a different mentality... what if he was in a bind and needed to get to work that day while his car was broken down? there are alot of what if's I guess... but, what does it hurt to ask?
on the other hand... If I see the same guy riding like that day after day... then, i'll assume he's ok with the situation. who am i kidding... i'd probably still ask if any help was needed(maybe lighting the way) only once though.
that being said... no need to feel guilty about it bane.
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Bikes: C'dale, Trek, Cervelo and Santana