Anna Leigh Waters is taking over Times Square, which is also a pretty good look for pickleball. With more gold medals than most players have matches, she’s redefining dominance in sports. Her latest spotlight? A billboard campaign that's putting pickleball front and center in one of the most iconic places on Earth.

Keep reading for:

• How to actually play singles

• Pickleball shoe review

• A matchmaking pickleball event with a twist

📰 Pickleball Legend in Times Square

Anna Leigh Waters is more than a pickleball champion—she’s becoming the sport’s global face.

Billboards featuring Waters have been spotted across New York City, including an eye-catching one in Times Square. Touting her accomplishments—over 151 gold medals and 34 triple crowns—these displays aim to introduce her dominance (and pickleball itself) to a broader audience.

She’s long been a household name in the pickleball world, but this campaign signals a new chapter.

And it’s a very well-deserved accomplishment, if you ask us. ALW is just 18 years old and has already accomplished the following:

• Went pro at age 12

• Has earned over one million per year in contracts alone for the last couple years

• Consistently a #1 pick in Major League Pickleball teams

• Multiple US Open championship wins

Waters is now positioned alongside sports legends, not just in the eyes of fans but in the heart of one of the busiest cities in the world.

Around the Picklesphere

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😆 They can’t keep up with us!

🎯How to Play Singles in 3 Easy Plays

BRING THIS TO THE COURT: Regular doubles players often have trouble even visualizing how to play singles — it looks, and often feels, like so much physical strain.

But you can and should try playing it, especially if you can remember the following plays:

• Deep Serve + Shadow: Serve deep from the centerline, then follow the ball’s path to stay in position, cutting off any angle returns. Think: depth over power.

• Corner Drive + Net Rush: Aim a forcing shot to your opponent’s weaker side (usually the backhand), then advance to the net if they’re stretched or off-balance.

• Return + Read: A strong return sets you up for control. Watch their position: if they stay back, move in. If they’re already at the net, choose your shot wisely—drop, drive, or lob.

Bonus tips: Target the backhand, stay centered, and don’t overuse the lob unless it’s surgical. Singles might feel intimidating, but it sharpens your entire game.

🔗 More singles strategy

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📺 Gear Review: Sqairz Pickleball Shoes

Gina and Neil unpack everything you didn’t know you needed to know about Sqairz shoes: how they feel, how they move, and how they hold up after real play.

And while both had a lot to say, Neil came away with a bold claim: he’s officially switched to Sqairz full-time. 👀

▶️ Watch the full review on YouTube

Pickle & Pair: Single Men Needed!

A new kind of pickleball event is stirring things up in the Cayman Islands—but it’s not about competition, it’s about connection.

IslandSoul, a wellness brand known for creative community events, is launching Pickle & Pair, a singles night built around social pickleball play and matchmaking software.

→ The concept: Attendees fill out a personality-based questionnaire, mix and mingle on court, and later find out who their match is.

The event has already generated strong interest from women, but organizer Kieri Dornan says they’re still looking for more single men to balance the playing field.

Set for June 8 at The Roost, the evening blends lighthearted sport, romantic intrigue, and holistic community-building.

From solo strategy wins to (literal) singles pickleball and rising icons, this week proves one thing—pickleball isn’t just growing, it’s evolving in every direction.