Brush one side of each bread slice with olive oil. Spread the other side of each slice with mustard.
Layer cheese, ham, lettuce and pear together on each sandwich. Grind some pepper on the sandwich and top with the other slice of bread.
Place on skillet or griddle and weight down with something heavy (small skillet or a large can of tomatoes work well). Cook until golden brown. Flip and cook until second side is golden and cheese is melting.