Updated Dating Guidance

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.

Reader response

Dear Amy: 

“Hoping for Companionship” is a 77-year-old widow who asked about jumping into the dating pool.

Your suggestions: Go to a museum? A coffee shop? Jeez, we’re old – not dead!

Why not suggest picking out funeral urns?

What’s wrong with playing nine rounds of golf, going fishing, watching your grandkids play sports? How about attending a street fair, county fair, mini-golf, or going to a local karaoke establishment? Do something fun and different.

My mom was 84 and was dancing at polka parlors until her death. She met men but dropped them when they’d say, “Oh, I go to bed at nine, so I can’t go out that late!”

Museum equals boring! I did that enough when my kids were small.

If they have a health restriction, moving might be helpful.

I’m not saying they should kayak down the rapids or join a pickleball team, but it is possible, I guess.

Who pays the bill? Easy! One pays for dinner the other tips generously. One pays for the show and the other buys the snacks.

If funds are limited, they could watch a minor league baseball game. Go to a farmers market, rent a movie and order a pizza, pick apples and make a pie. My gosh, the sky’s the limit, so put away the bingo cards and enjoy life!

– Disappointed

Dear Disappointed: 

Thank you for your great ideas.

I’ve been a life-long geezer, so I suggested first-date activities that are simple, inexpensive, and which I happen to enjoy.

Updated June 6, 2024, with the reader response

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.