1. An expression said when one is excited, pleased, or pleasantly surprised. Oh boy, a lot of people sure came to the fundraiser! A: "We're going to spend summer at Grandma and Grandpa's lake house!" B: "Oh boy! That will be swell!"
2. An expression said when one is frustrated by, exasperated about, resigned to something bad or unpleasant. Oh boy, another surprise inspection. I sure do love these. A: "Hi, Mr. Peterson? I need you to come in to the school and have a talk with us about your son." B: "Oh boy, what has he done now?"
1. Inf. Wow! (Usually Oh, boy! An exclamation. It has nothing to do with boys.) Bill: Oh, boy! An old-fashioned circus! "Oh, boy!" shouted John. "Dinner smells great! When do we eat?"
2. Inf. I dread this!; This is going to be awful! "Oh, boy!" moaned Fred, as his old car stalled out, "Here we go again." Doctor: It looks like something fairly serious. Jane: Oh, boy. Doctor: But nothing modern medicine can't handle.
See also: boy