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A small, black box of a room with a slightly raised stage. At its centre, a black metal stool and a microphone, with cord, on a stand. Looking at the simple scene makes me sweat.
I feel for Jennifer Windsor when she strides on stage, wearing a pair of bright pink Oxfords as she grabs the microphone to embark on one of the most terrifying challenges of her life. At 60, Windsor is about to perform her first standup routine before an audience.
She stumbles on the first joke and it doesn’t land. But now that the worst has happened, Windsor rebounds: “I aged a lot during COVID,” she says. The line is a gateway to solid laughs with jokes about binge-watching Tiger King while smoking a lot of pot and ordering fatty foods from delivery apps.
“The only way I will get a smoking hot body again is if I’m cremated,” says Windsor. I couldn’t help but wish I’d written that.
Some folks retire, quite literally, in their 60s — stepping out of life’s fast lane and heading directly for a quiet, introspective back road, perhaps near a burbling stream. Not so for Windsor.
“When I see the people in my life who seem the oldest compared to their age, it’s the ones that have lost curiosity in the world around them and are turned inward, and looking backwards,” she says.
That’s not how Windsor wants to live. The single, self-employed graphic designer, illustrator and dog lover has set out to seek new experiences as she ages.
“It doesn’t have to be a safari in Africa,” she says. “It could be just doing something that’s challenging. And I couldn’t think of anything more challenging than making funny jokes in front of a crowd into a microphone.
“And I’ve already been to Africa. Twice.”
Windsor hasn’t spent her life pining to tell jokes professionally. It crept up on her, during COVID, when she was home alone and stumbled into an online life coach looking for volunteer clients to complete his training. During the free counselling that followed, Windsor revealed she’d always wanted to write. That led her to a course for which she created some personal stories, including a comedic piece about Barbies.
When COVID loosened its grip, Windsor signed up for an Edmonton competition known as Story Slam. It sees folks gather monthly in a pub to tell each other five-minute tales. Windsor won top prize her first night out for the Barbie story.
“I was hooked on people laughing. That felt really good,” she says. “Full disclosure, it’s quite narcissistic.”
After winning Story Slam seven times in just over two years, Windsor was ready to expand her reach. She found a $450 course in standup delivered at an Edmonton theatre called The Grindstone. Over eight weeks, she and her classmates polished a five-minute routine. I went to their graduation showcase; it was surprisingly good.
Windsor wasn’t the only person on stage over 60. For those folks, the jokes, often prompted by cue cards, ran predictably to aging (loss of a spouse, vibrators, death cleaning, weight gain). But among the clichés of comedy (“I don’t know about you, but …” and “Don’t get me wrong, but…”) there were some pretty funny lines.
And here’s the thing. The room, stacked with friends and relatives of the showcase participants, was loving and supportive. I’m not a big public laugher, but surrounded by all that kindness and fun and the odd moment of hilarity, I chortled and hooted, too. It felt great.
Some in the showcase expressed a desire to become a professional standup. That’s not Windsor’s goal. Rather, telling stories and jokes in public is her way of living well as she ages.
She has the same aging apprehensions as many of us, grey and shapeless worries that creep into sleepless nights. Windsor has severe back pain and fears ending up in a wheelchair. Like many creatives, she doesn’t know if she has enough money to age comfortably; a lot of her spare cash is going into jawbone grafts and dental implants to avoid the grandmother’s-false-teeth that horrified her as a child.
Windsor doesn’t worry about dying alone, but living alone can be scary. When she writes and shares stories in public, she feels more confident, connected. The experience, frankly, is thrilling.
“It’s not fun at all when you’re up there. I’m very nervous and the lights are shining right in your eyes and you can’t see the crowd …” she says. “I feel like a bug on a pin but I have this notion of how I want it to go and every time I get closer to that, I get this rush.”
She knows that at 60, with back pain and weight gain, her opportunities to get a body rush may be limited.
“I can’t do the physically thrilling things like downhill skiing and bungee jumping, So I have to get my thrills intellectually.”
I met Windsor in the hallway of the club directly after her set. She was still shaking, but she was also flushed with triumph. She had done it.
— Liane Faulder writes the Life in the 60s column. [email protected]