Love Letters

Getting back into dating at 58

A divorced woman wants to know how to deal with all these websites and apps; plus, the never-old question of “will they like me?”

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Q. Hi, Meredith.

I am a 58-year-old woman who has been separated from my husband for six years and divorced for over a year. I am just now feeling confident enough to try out dating but am unsure about the best way to go about it. For one thing, I hear men my age are looking for “fit, athletic, attractive” 40-year-old women. I like to play tennis and walk, but I’m not going to boot camp on the weekends, and my 40s are definitely in the rearview mirror. And putting my life out there on or Tinderover50 or whatever is so scary!

I haven’t dated since before Mark Zuckerberg was born. Any advice for a nearly, dare I say it, 60-year-old woman to gain confidence to start dating, and how to go about doing it?

— Almost Ready


A. You’re not going to like this, but the easiest way to meet a lot of people at once is to get on those apps and websites. The great thing about them is that they’re all about quantity and speed. The men who only want to date 40-year-old marathon runners will ignore you, which means you won’t waste any time on them.

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The other nice thing is that you won’t be putting your whole life out there. If you browse Match or any of the apps, you’ll find that personal information is kept to a minimum.

Sit around with a friend one night and make a profile for just one app. Do this while eating very good takeout. Maybe enjoy a beverage. It’s much less scary to jump in with someone who can laugh with you about the experience. If you don’t have that kind of friend, focus on finding one, because the most important part of the dating process is having someone to talk to about it.

Also know that almost everyone shares your questions. Every day there are new people on those apps who have no idea how they work. Every minute, someone is swiping or clicking on a profile for the first time. You’re not alone; take comfort in the fact that everyone is going through the nervousness together.

— Meredith


1. Put some thought into your profile. 2. Be ready for the onslaught of sharks going after “fresh meat.” This lasts only about two weeks. 3. If someone is not interested, they are saving you time and angst. Don’t obsess about it.



Good advice, Wizen. I’d add: If a guy doesn’t have a photo or claims he can’t post one because of a work policy, move on; he’s married. Also, paid dating apps tend to be of better quality (you get what you pay for).


I’m in a similar situation, having joined a dating site after the death of my husband. I was pleasantly surprised . . . at 57, the people contacting me have been age appropriate (52-62), with some as much as 10 years younger.


I recently dated a 58-year-old woman who was very attractive. She constantly made references to her ex, and they weren’t positive. Don’t do that.


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