Dear Kiki: Finding your footing again in 21st century dating

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Dear Kiki

Dear Kiki,

I am an attractive, retired, 65-year-old woman who was widowed some years ago. I’m happy with my life and ready to date again. I’m looking for a kind, professional retired or semi-retired man around my own age, and I’m having no luck meeting anyone. The problem is that I married my high school sweetheart, so I have never had to do this before. I keep hoping my friends will set me up, but so far I am still at square one. Please help!

— Lonelyheart in Le Claire

Dear Lonelyheart,

I am sorry to hear of your husband’s passing, and welcome you to the wild world of senior dating. My advice is to head straight for the internet.

Internet dating opens up your options and allows you to choose more specifically the kind of people you’d like to meet. There is a whole world out there of social and romantic opportunities. Nobody seems to do it the old-fashioned way anymore, even old-fashioned people. The classifieds are still an option, but even most of those are online these days.

With internet dating, you can set parameters and lay some of your cards out ahead of time, like the fact that you’re widowed, or that you want to meet someone close to your own age. This saves oodles of time that would otherwise be spent interrogating strangers about basic business (“so, what do you like to do?”) over cocktails. Instead, you can use this time to actually do things you like to do, and when you meet someone you really click with for a date, you’ll know for certain that you’re both interested and available.

Use a well-established site frequented by professional adults, like or OKCupid, and go ahead and shell out for the membership. If you’re feeling adventurous, you can also try googling “Dating over 60” and you’ll find tons of options.

Of course, you can also continue trying to meet someone in real life. Make it known to friends you’re on the lookout for someone to get sweet with. Go out to events you’re interested in, sign up for some volunteering, classes or activities in your community. Call up some old acquaintances and go out for coffee to practice what being on a date is like. And most importantly, trust that there is plenty of love in this world and it will happen when and how the laws of the universe make it so.

You may very well meet a man the old-fashioned way, through friends or colleagues, or sitting around batting your eyelashes at a fancy restaurant, but why limit yourself? Your silver fox may be prowling just a county or town away, praying every night for a lovely lady to take on a riverboat cruise. Life is short, and there’s lots of love out there. Happy hunting!

Coffee, bagel, Little Village.

Make local news a part of your daily routine.


— xoxo, Kiki

This article was originally published in Little Village issue 207.

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