Dave Barry is American journalist who gained popularity writing for a regional newspaper Miami Herald and thanks to his talent and sense of humor became famous around the U.S. and abroad.
The essay "Breaking the Ice" is the thoughts and recollections of the author about his youth. It starts with the question which Dave Barry got from the young reader who asked the advice how to ask the girl for a date. As a reply, the writer told about his past experience in that deal.
According to the assumption that "there was always the possibility that the girl would say no", the author believed that the guy should avoid the direct request. He humorously concluded that after such an answer he needed "go into the woods and become a bark-eating hermit whose only companions would be the gentle and understanding woodland creatures. ... the woodland creatures would shriek in cute little Chip 'n' Dale voices while raining acorns down upon my head. “You wanna DATE? HAHAHAHAHAHA.”
So Dave Barry said:
"Never risk direct contact with the girl in question. Your role model should be the nuclear submarine, gliding silently beneath the ocean surface, tracking an enemy target that does not even begin to suspect that the submarine would like to date it. I spent the vast majority of 1960 keeping a girl named Judy under surveillance, maintaining a minimum distance of 50 lockers to avoid the danger that I might somehow get into a conversation with her, which could have led to disaster."
The author had a friend, Phil who was ready to help to arrange the date. "... after several thousand hours of intense discussion and planning with me, Phil approached a girl he knew named Nancy, who approached a girl named Sandy, who was a direct personal friend of Judy's and who passed the word back to Phil via Nancy that Judy would be willing to go on a date with me."
The main impression about the meeting (watching a movie in a cinema) was a tension. The author didn't feel confident, he wouldn't be able to communicate with Judy "without the assistance of Phil, Nancy, and Sandy". That feeling spread for everybody who was around. His mother who drove them to the cinema "was hideously embarrassing, had to pretend she wasn't there".
As a result of experience, the narrator gave advice for the young reader about asking the girl for a date: don't hesitate, pick up the phone and call her.
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