How 'Ask Amy' got its start

Ask Amy

Amy Dickinson, Ask Amy Ask Amy

Amy Dickinson is a general advice columnist.

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DEAR READERS: I'm marking my anniversary of writing the "Ask Amy" column, which debuted 10 years ago today. In honor of this, I'm rerunning the very first Q&A I ever tackled. I hope you'll agree that it's a classic.

DEAR AMY: This is my first time writing to an advice columnist, so I guess we're starting off together. Here's my problem: I'm in my mid-50s, divorced and have recently developed quite a crush on a lady who is a customer at my work. Although I am reasonably well educated and have enjoyed professional success in the past, present circumstances have me working as a clerk in a gas station-convenience store.

The lady has recently separated from a successful businessman and has been used to a rather glamorous and sophisticated social life. I sense that she likes me, but she knows me only in the context of a gas station attendant. How do I let her know that I care for her and, more important, have a lot more to offer than meets the eye?

Ken from Hinsdale

DEAR KEN: How's about a free package of Slim Jims? That always works for me. Don't overplay your hand, though.

First, pay close attention to her behavior. If she is buying her gas a gallon at a time or has recently developed a taste for microwavable entrees, she is most likely finding reasons to enjoy your company. And good for you!

Show a sincere interest in her -- not just her octane choices. Because, guess what: Women really like nice guys who pay attention.

My instinct tells me that a recently separated woman with a sophisticated social life might be lucky to find someone like you to lend a refreshing balance, even though she might not be ready for a full-fledged relationship.

And you get the first crack at the Lotto tickets, which is no small thing. (2003)