Ask Amy

Ask Amy column

I’m marking my 10-year anniversary of writing the “Ask Amy” column by rerunning some of my favorite Q-and-A’s.

Q. I am a 46-year-old, never-married man who has not dated seriously in more than 20 years.

Recently, I have become curious about a phenomenon I have noticed: It seems to me that women in their 20s are exponentially better-looking than they were when I was in my 20s and first moved to the city.

Don’t get me wrong — I fully realize I am too old to try to date them, and I seriously doubt that I have become less repulsive to them as I have grown older. I would just like to know if there has been an actual demographic change, if this is merely the glandular consequence of middle age, or if it is due to global warming?

Perplexed in Chicago


A. I agree. Young people do seem to be exponentially better-looking than when you and I were in our 20s.

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Perhaps we belong to a distinctly unattractive generation. Maybe we can blame this phenomenon on the style of the 1980s. No one can look good in a mullet.

Or perhaps it has to do with our eyesight — and theirs — because have you noticed that as you approach middle age, you seem to be growing ever more invisible?

Talk about macular degeneration. (2005)

Q. I got engaged at Christmas, and a few days later we visited my fiance’s aunt. My fiance’s sister was there. She took me aside and said, “You’re not good enough to marry my brother. In fact, the only one he should be married to is me.”


She is 23, married, with a son. I am 20 and my fiance is 28. His sister broke up the last girl he went with. What should I do?


A. First you should ask your fiance for a thorough explanation of this sisterly attachment, her comment to you, and her history of breaking up his relationships. Even if you find his explanation plausible, I think you should then opt for one of two choices:

1. Insist on a very long engagement. You need to see how much of an impact his sister has on his — and your — life. If this is a once-a-year comment from someone you rarely see, you might find it easy to ignore.

2. Lace up your fastest sneakers and run for the hills.

Either way — tread carefully. When you marry your guy, you marry into his family. His sister’s attitude toward you is unlikely to change unless he insists upon it, and he should insist upon it. (2004)


Q. I was under the impression that when you coordinate and make plans for the night, dine at a hip restaurant, and have drinks and make out at a hip bar, that constitutes a date. And when you do that serially with one person who coincidentally is not seeing anyone else, it’s called “dating.” She thinks we’re “hanging out.”


A. It’s all semantics. Stop picking at this and enjoy yourself. (2005)

Q. How long is considered an appropriate length of time to wait for someone when a date/time has been agreed upon to meet at the theater, a restaurant, museum, gallery or the like?


A. I’m a 20-minute-limit gal, with exceptions made for people who are circling the lot looking for a parking space and for my cousin Jan, who is always late but worth the wait. (2004)

You can contact Amy Dickinson via e-mail at askamy@tribune
. You can also follow her on Twitter @askingamy or “like” her on Facebook.