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Ask Amy: Amy plays 'Cupid' in classic column

Amy Dickinson

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-and-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 microwaveable 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)

DEAR AMY: I moved in with a woman seven months ago after leaving my wife of more than 30 years. The agreement was that I would move in and she would stop smoking at that time. She did try twice to stop, using pills she bought on the Internet, but to no avail. She now smokes heavily.

I contend that she didn't live up to the agreement as I did, but she has difficulty with my saying so and feels I am trying to control her. I say it's not about control but about giving herself health problems and exposing me to harmful secondhand smoke. — Secondhand Smoker

DEAR SECONDHAND: It seems that your live-in has broken her agreement with you, but I can't resist pointing out that, according to you, you broke your own agreement with your wife of 30 years. What you're seeing is that these covenants are only as strong as the individuals involved. (2004)

DEAR AMY: "Pat" and I have been dating for a few months, and things are great between us — for the most part.

Pat has a 160-pound Great Dane that he allows to sleep in bed with him. When I spend the night at his place, his dog usually sleeps with us and there is not enough room for the three of us, so Pat usually sleeps on the couch or in the guest room.

I don't like this arrangement and don't think the dog should be sleeping with us, but also feel it's not my place to say anything. It's his dog and his house. How do I tell Pat that I want to spend the night with him, not his dog?

I am getting to the point where I don't want to spend the night with him anymore. I know he feels my frustration, but we've never discussed it other than him saying his dog is overly spoiled.

Please advise? — Doggone Tired

DEAR DOGGONE: Are you telling me that when you go to your boyfriend's house, you end up sleeping with his 160-pound dog?

And you can't manage to say, "I want to spend the night with you, not your dog?"

Here's how I see it: If you're brave enough to risk a nighttime encounter with Marmaduke, then surely you're brave enough to start a conversation. (2004)

(You can contact Amy Dickinson via email: askamytribune.com. You can also follow her on Twitter askingamy or "like" her on Facebook. Amy Dickinson's memoir, "The Mighty Queens of Freeville: A Mother, a Daughter and the Town that Raised Them" (Hyperion), is available in bookstores.) 


By Amy Dickinson
Tribune Media Services