I'd ask if he wanted you to cut it for him, or else show him how to cut it by laying the cutter flat on a table and standing the cigar upright and cutting it that way. Perhaps teaching him a little about cigars will go along way to him enjoying cigars more often.
It's like the old saying "Clip a cigar for a man and he'll smoke for a day, Teach a man to clip and he's wife will hate you for 10 lifetimes"
