Finding (and Losing) Joy on the Pickleball Court

It was Covid, and my tennis buddy kept trying to convince me to try pickleball. Every time we hit tennis balls, I scoffed — no way was I trading in my racket. Then one day, she showed up with a bag of two paddles and two balls.

My daughter and I went out to give it a try. I had the time of my life. A guy named Robert and his friend Mary taught us the rules and kept score, even though we were totally confused. They were so patient.

At one point, I smacked the ball as hard as I could straight at Robert. I started to apologize — but he just popped it right back.

It was love at first sight. Love at first hit.

Then I learned about “open play,” where you could just show up and meet people. It reminded me of pickup basketball, which I loved because you didn’t have to plan anything — you just showed up and played.

The more I played, the more I wanted to play. I felt like the sport was made for me.

I found a partner and we started playing tournaments. He was definitely my pickleball sports crush. Paris and I had a blast, and I got my first DUPR rating. We signed up for as many tournaments as we could.

But then it stopped being fun.

We started playing against twenty-something former tennis players — fast, strong, and relentless. It was demoralizing. My rating dropped. I watched it sink lower and lower. I’ve never thought of myself as a sore loser — in fact, I love being the underdog — but it got harder and harder.

In one of our last tournaments, we played against this woman, Chloe, who was quite athletic and her partner, a 6’7” giant who was at least 30 years younger than me. Even though I played out of my mind — hitting ridiculous angles and overheads, even successfully lobbing the giant — we got beaten handily. He even finished the match with an ATP.

Afterward, Chloe reached out and asked if I wanted to partner with her. I was so honored, I said yes immediately.

She invited me out to her courts so we could practice together and see if we were a good fit. She made a comment about me being a 4.0+ player. I broke it to her that I was only a 3.7. Not sure if I imagined it, but it seemed like her jaw dropped at least 4 inches. But we’d already signed up for two tournaments.

In the first tournament, I got the worst case of the yips imaginable. I couldn’t get a serve in. Between games, we’d go to another court so I could practice while she patiently returned balls to me.

Despite my performance, we won a bronze medal — and I truly believe on any other day, we could have taken gold.

Then came the big APP tournament in Sacramento. I tried to give Chloe an out, but she didn’t take it. She stuck with me.

Unfortunately, I played perhaps the worst pickleball of my life. Completely whiffing overheads, returns into the bottom of the net, balls slicing wide, simple dinks into the net, volleys thudding off of my paddle or worse, popping up so that they could smash it at her…

We lost our two matches, 15–4 and 15–2 in less than 45 minutes total. Chloe was nothing but kind to me. But I couldn’t help but notice the tight jaw.

I drove back to the Bay Area with my tail between my legs — bruised ego, $175 poorer. (More on tournament pricing/gouging another time.)

Over the years, I’ve collected a few medals, which now make great Christmas ornaments. But overall, the tournament scene has been discouraging.

I decided to take a break from tournaments and just play in low-key ladders. Some games were great — competitive and friendly. Others felt like dentist-chair torture: when one player is substantially weaker and gets mercilessly targeted, every point becomes awkward and painful for everyone. Nobody likes a pickle. (11-0)

I tried joining a higher-level mixed ladder (4.5), and while I loved the challenge, I was often the weak link. I didn’t mind getting targeted, but I could tell it wasn’t fun for others, and that started getting to me.

So, I stepped away from that too — for now. I’m working hard to improve, and maybe someday I’ll be back.

In the meantime, I’m just trying to find players around my level and bring back the joy.

I’m sharing this because my story isn’t unique — I hear these tales of love, heartbreak, and frustration all the time.

I don’t know exactly what the answer is.

But what I do know is this:

It’s a game.

And games are supposed to be fun!