Dating In My 50s is Like Taking a Trip to The Island of Misfit Toys

We’re all looking for someone to love us just as we are.

kasey sparks
Published in
4 min readNov 4, 2024

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a quirky and lovable monkey made of socks with earnest looking eyebrows
quirky and adorable | Photo by Denisse Leon on Unsplash

Sometimes I wish I could begin all my first-date conversations by diving right in and asking a very direct question.

In what ways are you quirky? I’ll go first and share one of mine.

I’m tidy. I have two lazy susans in my cupboard holding my spices. The jars are arranged alphabetically AND by height. Can you live with that and more importantly can you return the jars where they belong when you’re done using them? Because if the rosemary ends up next to the basil I may go crazy.

That’s just one of my quirks, mind you.

My routine is established. I know where I want the scissors kept and how I like the towels folded. I know what I need to feel secure in a relationship. Sometimes it’s hard to imagine how anyone could tolerate all my quirks.

I’d follow up this quirky question inquiry with a few more that are perhaps a bit more vulnerable to answer.

What do your cracks look like? How have you been shattered?

If we’ve reached middle age with an I’m single status there’s a good chance we’ve had something hard happen. A death of a spouse. A divorce. A dream of marriage…

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kasey sparks
kasey sparks

Written by kasey sparks

making mistakes · gathering lessons · sparking curiosity · wrangling words & fiddling with titles since 2017

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