Updated Dating Guidance

A 77-year-old widow is ready to start dating, but she needs updated dating guidance for this new era. Advice columnist Amy Dickinson offers her take on 21st-century dating for those returning to the scene.

Dear Amy:

I am a 77-year-old, retired professional woman who has been widowed for three years following a very happy and very long marriage.

I am now ready to begin dating, but am unsure how to proceed.

When I was young, the lady never did the asking. I’m not sure if that is still the protocol or whether it is acceptable and expected for me to call a gentleman I know to be single and ask for a date.

And if I do that, do I pay for the date, or is splitting the check the norm?

— Hoping for Companionship

Dear Hoping:

Yes — it is completely acceptable and expected for a woman to take the initiative and ask a man out.

Good first dates should be simple, inexpensive, and designed for the ease of conversation. A walk in the park followed by coffee, a visit to your local museum, botanical garden or historical society followed by coffee or a drink — chose something nearby and easy.

The person initiating the date should offer to pick up the entire check, but splitting the check is the norm — although a man in your generation might want to pick up the check, even if you’ve invited him out.

Which reminds me of a moment from a classic movie about adult dating, “Sleepless in Seattle,” that these days if a man offers to pick up the check, women will throw a parade for you.

Get out there! And good luck.

In the tradition of the great personal advice columnists, Chicago Tribune ’s Amy Dickinson is a plainspoken straight shooter who relates to readers of all ages. She answers personal questions by addressing issues from both her head and her heart. A solid reporter, Dickinson researches her topics to provide readers with informed opinions and answers – ranging from updated dating guidance for seniors returning to the scene, to a man who lied about being a veteran, and risky downsizing strategies . Ask Amy, P.O. Box 194, Freeville, NY 13068.

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