Someone in Chicago is looking for a boyfriend — emphasis on friend

A 92-year-old widow wrote about an issue people of any age can relate to — a desire for a companion, along with the insecurities that come with putting yourself out there.

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A 92-year-old widow wants a companion and wonders what she could do to get a boyfriend.

A 92-year-old widow wants a companion and wonders what she could do to get a boyfriend.

Angela Cheng / Sun-Times

An advice column where Chicago can ask questions on how to navigate life transitions, relationships, family, finance and more.

Dear Ismael,

I’m a well-preserved, attractive, well-dressed 92-year-old widow in excellent health. I am fortunate to live among many good people of all sexes, with good friends in each of them. But I would love a male companion. Not for sex (although cuddling would be nice) but for companionship. I know I look (and act) more like someone in her 80s (if not late 70s) but we tend to celebrate birthdays where I live, so everyone here knows my age. How do I go about getting a (straight) male boyfriend, with the emphasis on friend?

— Seeking male companion in Uptown

Dear Seeking,

You have lived about three times what I have, and I am sure you have collected great wisdom throughout the years, but here’s some perspective from someone in their early 30s:

Everyone you know, of any age, should have an available brother, cousin or friend they think could be a good fit for you. Put it out into the universe and let the good people around you know that you are ready and open to sharing your life with someone again.

Most of the time people will automatically think about reasons why something wouldn’t work out with someone, whether it’s looks, emotional availability or personal circumstances.

Need advice?
Submit your question to ‘Someone in Chicago.’
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“Is she single? Is she already talking to someone else? Is she done with men?”

It’s easier for people to open up to the possibility of giving themselves to someone when they know that other person is ready to have someone in their life.

Increase your chances of meeting someone by getting rid of uncertainties and by giving men a reason to know why a relationship with you could work. The first possibly being, “She’s looking for someone. I am, too.”

How can age influence your chances of finding love?

What I have learned simply from swiping on dating apps is that age and attractiveness can be very subjective. There is no exact science that tells us what age is the sexiest.

There are times someone who is 48 could be more attractive than someone who is 28. Even then, people who are the same age, say 35, can look so different. Some may have a baby face, others might look mature enough to have a beer with my gray-haired dad after work.

In the real world, I’ve seen high school kids struggle with early signs of baldness, and witnessed athletic retirement-aged men run past me at the park while I’m out of breath from simply walking.

So when it comes to potential companions knowing you are 92? I say show off your age with pride. If you feel confident enough to give 70- and 80-year-old women a run for their money, put on your favorite lipstick and your nicest dress and do it.

Don’t let self-doubt overshadow what you know makes you feel beautiful, or keep you from what you desire. And if someone does have an issue with your age, don’t bother with childish 80-year-old men.

Write to “Someone in Chicago” at someoneinchicago@suntimes.com or fill out this form.

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