As the title says, you probably won’t. Actually, you might get a lot better quickly by playing the same people over and over, depending on your current skill level. By simply practicing your serve, dinks, footwork, etc, you’ll definitely get better. Eventually, however, you’ll plateau. And if you consistently play against players with a lower rating than you, you’ll likely get worse.

I play with the same three guys i’ve always played with, one of whom introduced me to the sport of pickleball four years ago. When I play opposite of him, I know exactly the speed of his serve, where he’ll likely return my serve, and exactly when he’ll throw his paddle in a fit of frustration when I deliver him a put-away shot (although on one or more occasions his paddle has whipped right by my ear unexpectedly and i’m lucky to have walked away from the match unscathed.) It’s all part of the experience in our fun little circle of middle-aged married men looking for an outlet to get through the grueling week.

The point is (an obvious one to say the least) that after a few months of playing in the same group, I felt as if I was just going through the motions, having fun on the pickleball court without getting much better at the game. For 90% of recreational players, this can be perfectly fine. It’s the other 10% who live and breathe this game that want to get better, learn the game on a deeper level, and move on to playing competitively in tournaments.

I came to this realization a few weeks ago when two of the four from my regular pickleball group had other commitments that prevented them from coming to play on our regular Tuesday matchup. That left Joey and I (two solid 3.5-4.0 players) playing some singles at the local park behind my house. After two grueling, knock-down-drag-out games, several of his friends unexpectedly showed up to pickle, and we invited them to play doubles.

Playing pickleball against strangers is one of the most thrilling and rewarding experiences for someone obsessed with this game. Their serves were unpredictable, drives we’re harder, and their cross-court dinking impeccable. I moved my feet more in those three games than I ever had, and I was better for it. Just like a stagnated bodybuilder shocks the muscles into growth by changing up his/her workout routine, you, too, can force yourself to become a better pickleball player by playing outside of your circle. I recommend hitting the pickleball courts on a day apart from your scheduled pickleball day and mix it up with some randoms. Your game will thank you. That’s my story, and i’m sticking to it.