Someone in Chicago wonders where to turn when dating sites aren’t an option

No matter our age or circumstances, we all need options.

SHARE Someone in Chicago wonders where to turn when dating sites aren’t an option
An illustration portraying two swans crossing paths.

No matter our age or circumstances, we all need dating options.

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,

What can an 85-year-old woman do when dating sites don’t go up to that age?

I’m seeking a male who can fulfill this directive: It’s your turn to walk the dog. Note that this plea reveals several things about the male I seek. He is a dog lover, which is essential for anyone who enters my life. Two, at an older age, he has the physical capability to rise without assistance and walk steadily holding a leash. And, three, he doesn’t balk at this dictate, instead finds it charming.

Since online dating sites bar the door from me, I’ve had to be creative in my quest. Not only because of my age, but my, um, preferences. My potential match must be a reader of daily newspapers, local and national. I read online, but listening to the rustle of his pages turning would be melodic to me.

Although I am both a divorcee and widow, I’d prefer the latter. Someone wistful about a partner gone home to a better place, rather than a bitter spouse left behind with scores to settle.

Dog and I live in a high-rise, with an elevator as our means of exit and entry. Oh, how we long for a front porch and a backyard. (I’m assuming my pet dreams similarly.)

So, Ismael, if you really want to take on a challenge — particular to me but likely shared by many in my cohort — here’s your chance.

— Dog lover in River North

Need advice?
Submit your question to ‘Someone in Chicago.’
ASK

Dear Dog Lover,

You Chicago widows are really putting me to the test. And after reading about the type of man your heart desires, I’m sure I wasn’t the only one hoping there was a romantic dreamer flipping or scrolling through the newspaper and picturing himself fulfilling that role.

What I’ve realized (and hopefully other smart businesses in the city begin to notice) is that there is a matchmaking market for people over 80 who yearn for another chance at love.

Because you’re right. I’ve complained about how dating apps are limiting and challenging for people on the younger side — but what about those who are literally excluded because their age doesn’t appear as an option when signing up for those sites?

I’ve written before that we need to keep on searching through the “rights and wrongs” in order to put together the version of the one we want, and hopefully get somewhere close to that description when we find them. At 85, you clearly know what you want.

Although it is annoyingly true, we can only hear “You’ve got to keep putting yourself out there” so many times, especially when you are limited to dating experiences where other hopeful lovers roam.

No matter our age or circumstances, we all need options. The next big thing, after dating apps, is physically seeing prospective partners lined up and ready to answer if they love dogs or not.

I’d like to extend that challenge of yours to Chicago businesses and community groups who can afford to create a welcoming space where lost lovers can find another chance.

And I’d like to know from those in the dating pool: What would the perfect dating event experience be for you? What type of curated event would be worth putting yourself out there? I might give speed dating a go and report back.

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

The Latest
The Sox have won four straight for the first time this season, and the first time since a seven-game run last June.
The man was outside when someone approached him and fired shots, grazing his ear.
The Sky will likely decide between signing guard Kysre Gondrezick and rookie Brynna Maxwell after guard Chennedy Carter’s strong training camp.
Before Saturday’s game against the Guardians, manager Pedro Grifol wasn’t ready to commit to keeping Ramos in Chicago.
Cubs lefty Justin Steele struggled, and MLB’s top pitching prospect Paul Skenes made his major-league debut.