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Ask Amy: How does this 70-year-old widower meet women to date?

Dear Amy: I am an almost 70-year-old widower (politically liberal and atheist) who wants to meet new people. Especially female people. Unfortunately, I have almost no experience.

I had a total of two dates in high school, both of which went nowhere. I became very good friends with my best friend’s wife (friend-in-law?), and when they divorced, she and I got married. So when it comes to wooing and flirting, I’ve got nothing.

It has been four years since my wife died, and I have had zero possible romantic encounters. My only teacher has been rom-com movies, which I am told do not portray real life. Sadly, I was planning my run through the airport already, but now I’m lost. Where should I go to meet a possible romantic interest?

Denver: Assuming that you are respectful, presentable, self-supporting — and that you can still drive at night — I’ll paraphrase a line from “Sleepless in Seattle” and say, basically, that the available women will throw a parade for you. You just have to locate the best parade route.

You may have spent the last four years in a fairly solitary state (understandable, given a global pandemic and the loss of your wife). If so, you might do best to view this as an effort to meet and make new friends (rather than to find women to date). You should pursue activities that align with your interests, and then — start showing up. You live in a large urban area with a lively arts scene and surrounded by spectacular natural wonders. Start to explore! ( is one way to find groups to join.)

Your best friend’s wife found a reason to leave him and then marry and stay with you, and so I’d say that you’ve probably got a bit of Tom Hanks in there — somewhere. Friends can help to “polish” you and even take you on practice runs where you can work on your greeting, meeting and connecting skills. (In a rom-com, this would involve a montage of misfires, until you had proved your readiness.) Friends can also introduce you to available women.

There are a number of online dating sites designated for “silver singles” like you. Peruse and research these sites to see if you are ready to meet women virtually.

Dear Amy: Not only am I the only remaining Jewish person in my immediate family, but I became more observant as my parents’ chief mourner/Kaddish.

I plan my life around our holidays. I’ve noticed that my beloved nieces and nephews do not acknowledge these holidays and do not wish me a “Happy …” holiday.

Should I say something? Do something? How can I feel better about this? I am single and without children, and — other than this — these relatives are a light in my days.

Oy Vey!: I take it that you and your siblings were perhaps raised in the faith and that your siblings have drifted or are lapsed. If so, your siblings would not have raised their children following the holidays and rituals surrounding the Jewish calendar.

Because Jewish holidays are scheduled according to a lunar calendar, for those following the Gregorian calendar, these holidays can seem to float throughout their seasons. So, for instance, the Rosh Hashanah (the new year) doesn’t always fall on Jan. 1. Hanukkah doesn’t always begin on Dec. 25.

Perhaps you could increase their awareness by offering your nieces and nephews a glimpse into your world. For instance, you could send out an email at the start of a holiday, tell them what it is, and briefly describe the holiday’s meaning and the practices surrounding it. Don’t try to recruit or convert them, and don’t blame them for their ignorance or lack of interest. Keep the message short and simple, and sign off with affection.

Dear Amy: Regarding “Ivy Leaguer’s Wife,” the woman who wanted her husband to wear a shirt with his law school’s logo on it: Why do you immediately assume that this Ivy Leaguer would be privileged? It’s stereotypical to think that everyone who attends an Ivy League school got there because of “privilege,” a word that is thrown about way too often these days. He may have worked tirelessly to pay for and attend this school!

TT: I don’t assume that anyone who gets into an Ivy League school is “privileged,” but I do assume that a lawyer who graduates from one of these prestigious law schools is.

© 2023 by Amy Dickinson. Distributed by Tribune Content Agency.

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