Every pickleball court has its regular cast of characters, but some of the toughest competitors don’t look the part. They’re the ones you size up as an easy win… until the first rally. Suddenly, you’re grinding for every point and realizing this match won’t come easy.

Consider it a reminder: don’t judge a book by its cover. These unassuming players are the ones who will make you work for it.

Grandma who’s been playing since the 70s

Gloria, Doreen, Joanne—whatever her name is—this grandma is about to give you a proper lesson on the pickleball court.

You clock the knee brace, the slightly hunched posture, the Skechers, and think you’ve got this in the bag. Then the first few points happen. Suddenly, you’re chasing balls you can’t reach, getting passed at impossible angles, and wondering how she’s controlling every inch of the court without breaking a sweat. She’s taken maybe three steps all rally and still picked you apart with surgical precision.

Getting beat by a grandma is basically a pickleball rite of passage. Don’t stress it. Keep practicing… and maybe, eventually, you’ll get one back.

The tennis moms

These divas? Quietly lethal on the pickleball court.

They roll in right after school drop-off, smiling, chatting, giving total “someone’s mom” energy. They’ve got a tight window—just a few games before a full day of errands, the gym, dinner prep, the vet, and shuttling Billie to soccer. You see the minivan, the packed schedule, the friendly vibe… and assume you’ve got the edge.

Then the paddle comes back on that forehand.

All of a sudden, it’s a full-on tennis backswing and you realize you’re in trouble. She flips a switch, and now she’s locked in like it’s Championship Sunday. The intensity is real, the forehand is a weapon, and every ball is coming back deeper, sharper, and smarter than you expected.

She might miss a couple, but don’t get it twisted. She’s in control. Efficient, composed, and somehow always a step ahead without ever looking rushed.

And the worst part? She beats you. Every time.

No drilling. No fuss. Just straight-up execution.

Silent killer who’s a strategic mastermind

Then there’s the final boss of open play, the low-key killer you almost miss entirely.

He blends in. Nothing flashy, nothing memorable. Probably named Chris. Maybe he’s got glasses. Maybe not. Either way, he’s scanning the court like it’s a geometry problem you didn’t study for.

Chris isn’t here to chat. He’s polite, sure, but all business. Quick intro, light paddle tap, “0-0-2”… and then he’s already painting the front corner for an ace before you’ve settled in.

You might sneak a couple points. It won’t matter. Every shot you hit somehow becomes the exact ball he wanted, set up perfectly for him to finish. It starts to feel less like a game and more like a lesson.

Playing him is like getting a glimpse of what it’s like to face Ben Johns: methodical, precise, and a step ahead the entire time.

And when it’s over? A quiet paddle tap. A soft “good game.” He walks off to the advanced courts.

You’re still stuck on intermediate, wondering what just happened.

So next time you step onto the court for open play, pay attention to who’s across the net. The most unassuming players are often the ones who will test you the most.

They might not look like much, but they just might be your toughest matchup of the day.

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