Just saw this thread, caught the first wee bit and when he mentioned that one might have to use an entire book of matches to light a single cigar. Figured I'd share my thoughts.
Either the cigar is:
#1. Not made of Tobacco or.
#2. It is soaking wet o r.
#3. The matches are damp or.
#4. those are Asbestos matches or.
#5. the would be cigar smoker is using his feet to strike the matches and not enough or flexible enouth to bring the flame to the too short cigar or most likely.
#6 The person trying to light the cigar is the damp one..a Snowflake.