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The two are different in that the first means: Have you ever been issued another citizenship document? (i.e. you might not be a citizen of that country anymore) The second question asks about your current documents.
In general, having another citizenship (and passport) is not a problem when you enter the US under the visa waiver program as long as you show the ESTA-approved passport when boarding your flight and entering the US.
Important addition from the US customs and border protection web site:
Nationals of VWP countries who have traveled to or been present in Iran, Iraq, Sudan, Syria, Libya, Somalia and Yemen on or after March 1, 2011 (with limited exceptions for travel for diplomatic or military purposes in the service of a VWP country).