This is the time of year when things can get a little awkward for American tennis players, especially the men.

There’s no way to sugarcoat it. With a handful of exceptions, clay just isn’t really their thing, but come spring, they’re putting their feet in the dirt for four of the most important tournaments of the year, culminating in the French Open at Roland Garros.

Take a look around the complex near the Bois de Boulogne, and you can see things getting tricky point by point. There’s Frances Tiafoe needing five sets to survive an Italian qualifier named Mattia Bellucci, ranked 173rd in the world. There’s Chris Eubanks trying to figure out how to slide against Jannik Sinner (who, OK, is the world No 2) during what is, at 28, essentially the first proper clay season of his career.

He lost in three sets.

Then there’s Alex Michelsen, getting pasted by Alex de Minaur, losing 18 of 21 games in his French Open debut on Tuesday to an Aussie who doesn’t love clay either, despite having the movement skills to make it work.

An American man hasn’t won the French Open since 1999, a quarter-century ago, though the Bryan brothers made seven finals and won two of them in doubles. The slower surface neutralized big servers and allowed their teamwork to thrive, Bob Bryan said. Before Andre Agassi’s triumph just before the turn of the millennium, Jim Courier won two titles during the first George Bush administration.

Agassi on his way to victory in 1999 (Simon M Bruty/Any Chance/Getty Images)

The women are little better off, especially those who grew up in Florida (more on that in a bit) having figured out how to keep Chris Evert’s staggering French Open legacy alive over the years. Serena Williams won three times, less often than at any other Grand Slam, but still nothing to sneeze at. Fellow Floridians Coco Gauff and Sloane Stephens have made finals in recent years.

But it takes some extra effort, both physical and mental. It’s uncomfortable. It’s confronting. Ultimately, when talking about the relationship between Americans and clay, it’s complicated.

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The red clay courts of Roland Garros are comprised of two centimeters of crushed red brick, spread on top of seven to 10 centimeters of crushed limestone, which sits on roughly 30 centimeters of crushed gravel. Tennis balls tend to slide as they bounce on hard courts and grass. On clay, the friction with those two centimeters of dust and condensed brick causes them to pop up, slowing shots by milliseconds that feel like an eternity to tennis players at the highest level, completely altering how they approach the sport. Clay-court tennis, like the fast, low grass season that succeeds it, is a praxis if not a philosophy: it reconfigures match-ups and puts accents and inflections on styles that can change a fight between two players from something one-sided into a much closer battle, or even flip it completely.

“I had to kind of just fully go all-in this year and just kind of, you know, see what’s with the dreaded, as some say European, clay-court season,” Eubanks said Monday after his straight sets loss to Sinner, as though he was speaking about a visit to the proctologist. Last year, Eubanks skipped Europe until the French Open, choosing to play Challenger events on hard courts in Asia. After all his success last summer, his high ranking prohibited him from entering those events this year — and the top-tier tour money is so much better. Danielle Collins said similar to reporters this week: practice and building momentum on a tricky surface is one thing, but practice doesn’t pay the bills.

Eubanks slides for a shot against Jannik Sinner (Anne-Christine Poujoulat/AFP via Getty Images)

The good news for Eubanks is that it wasn’t nearly as bad as he thought it would be. He thinks, one day, he might even be able to get pretty good on the dirt. The not-so-good news: He hasn’t won a match since he touched down in Europe more than a month ago. The biggest issue, he said, is the challenge of living out of a suitcase, bouncing from tournament to tournament without any time at home from mid-April until whenever Wimbledon ends in July. But the time had come for him to put on his big boy pants and give it a whirl. 

“At some point you had to just go all-in and try to figure it out,” he said. That “it” isn’t just a personal investigation into his game. 

The evolution of the complex American relationship with clay goes back to the middle of the 20th century, to the expansion of suburban life in the post-World War II years, and the subsequent tennis boom of the 1960s and 1970s. Tennis shifted from the country club to the public park, a favorite activity for an aspirational middle class. Local governments financed much of that through the construction of thousands of tennis courts. 

Grass ones? Of course not. Clay? Too expensive, too hard to maintain. Cheap, hard courts? Perfect. 

Where clay courts did exist, they were usually green, which are made from ground-up stone that is generally more durable and cheaper than the red stuff that has to come from special factories that process a specific kind of brick. Red clay became the surface of choice on the European continent, since it can accommodate play during the often drizzly afternoons, and in South America. In both places, lots of serious tennis happens more in private sports clubs than in public settings, which account for the overwhelming majority of play in the United States.

Keys thrived in Strasbourg (Johannes Simon/Getty Images)

The great surface exception was South Florida, a breeding ground for American tennis talent, where it rains seemingly every day in the middle of the afternoon. That necessitated plenty of green clay, which becomes playable more quickly than a hard court after a brief downpour.

“That was always the way that we were able to play as much tennis as possible,” Stephens said during a recent interview in Madrid, where she was in the middle of her favorite part of the year. “We can go on and off the clay courts. Hard courts, we always had to wait to dry and we had to squeegee them ourselves and that wasn’t fun. So clay just became the norm, and that’s probably why I just enjoy playing on it so much.”

Madison Keys, who just beat Danielle Collins in Strasbourg to win a WTA 500 clay title, had a similar experience as Stephens at Evert’s Florida academy. Gauff had it to some extent, but she also spent two or three months every year at Patrick Mouratoglou’s academy in the south of France, where she spent plenty of time on red clay.

The contemporary top of American tennis seems a little more willing to get down in the dirt than its predecessors.

With a handful of exceptions, the American pro ranks of the 1970s and 80s seemed mostly resigned to a bleak tennis midwinter, only one that came around every year in spring.

Americans played power tennis. Big serves, big forehands. Serve and volley. Adaptation? Transition? Concession? Not a jot. Hold your nose, get the dust out of your eyes, and wait for the green lawns and spiked soles. Plenty of players just endured April and May, and John McEnroe still gets queasy when he sees Court Philippe-Chatrier, where he coughed up a two-set lead to Ivan Lendl in the 1984 final.

That strategy became untenable when tennis decided to make red clay harder and faster, and hard and grass courts slower, to create longer, more compelling rallies. That made all tennis at least a bit more like clay-court tennis, where players have to grind and construct winning points rather than blast their way to them.

When Patrick McEnroe took over player development at the United States Tennis Association in 2008, armed with the knowledge that clay-court tennis had become foundational to the modern game, he decided he needed help. So he called Jose Higueras, a Spanish master of clay courts in the 1970s and 1980s who lived in Palm Springs, California. Higueras had convinced Courier he could be a top clay-court player in the early 1990s, helping him win those two French Open titles. Perhaps most importantly, Courier had believed him.

Now his mandate was to do that for another generation.

Higueras brought in Diego Moyano, a coach and former player from Argentina, and started with the basics. Slide to the shot not after it. Run with small steps, with your feet close to the ground. This is how to hit a drop shot. This is how you loop the ball over the net and buy time. 

A few years into the gig, he gathered a couple of young teenagers named Frances Tiafoe, Tommy Paul and Taylor Fritz for clay-court boot camps and trips to Spain for low-level tournaments.

Tiafoe on the slide in Sardinia (Mike Lawrence/ATP Tour)

 Fritz, a far better natural hitter than mover, remembers that first venture to Spain well, though he’d prefer not to. 

“I remember Diego spending a lot of extra time with me,” Fritz said recently. “I was literally falling, like falling down every single day, literally every day.”

Higueras said it was actually pretty funny.

“He was awkward,” he said of Fritz. 

Paul had an advantage. When he was growing up in North Carolina, his parents owned a small health club with green clay courts. That’s where he first learned the game. 

“I actually played more on clay than any other surface,” he said.

Probably not a coincidence that he was also the best American in his age group throughout his childhood. Then, when he was 18, he won the French Open boys title in 2015, beating Fritz in the final.

Had Higueras solved the American men’s red-clay riddle? Eight years later, it seems not so much. Tiafoe, Fritz and Paul have yet to make the second week of the French Open. But the reason for the endurance of the puzzle is no longer about an intrinsic reticence; it has more to do with the development of tennis as a whole, just like those court characteristic revolutions of two decades ago.

Paul said during a recent interview that making the jump from juniors to the top 20 has required him to become a more aggressive player, turning his game into something that works less well on clay, at least until recently. An ankle sprain in Miami in March forced him to skip tournament play for month, and allowed him for the first time to do a mini-clay pre-season during the first weeks in April.

“My coaches had been trying to get me to do that for years,” he said. “That injury was a blessing in disguise.” 

He sneaked in an extra week of training in Madrid after he lost his second match there, then made the semifinals in Rome and bulldozed Pedro Cachin of Argentina, whose favorite surface is clay.

Fritz said he doesn’t mind clay, especially in Madrid, where dry air and altitude make the surface more similar to a hard court. He actually thinks his forehand is best on clay, since he gets an extra beat and likes to spin it. His big problem with the French Open is the balls.

“Super dead, super soft,” he said. “They go absolutely nowhere. I can feel like I’m swinging as hard as I possibly can and the ball is not going.”

After a bumpy first set Tuesday, Fritz cruised through Federico Coria of Argentina 2-6, 6-1, 6-2, 6-1. 

Higueras thought Tiafoe might ultimately thrive on clay. Tiafoe said Higueras told him he could win the French Open one day. He’s still not a fan, especially when he connects with a ball just right, lashes it across the court or down the line, and then sees it coming right back.

“I just don’t think you get a reward for quality shots,” he said the other day of life on the dirt. “It levels everyone’s ability to extend points and be in points and have more of a shot.”

Hope springs eternal, though. As night fell Tuesday, a horde of American women were through to the second round, with Florida well represented by Gauff, Danielle Collins and Madison Keys and Sofia Kenin. Peyton Stearns, the champion on the red clay of Rabat over the weekend, won in a third-set tiebreak to advance, while Emma Navarro breezed through too. They might not get anywhere near Chris Evert’s seven titles, but they’re dispelling the idea that it’s OK to give up on the red stuff.

Evert winning one of those titles in 1986 (Trevor Jones/Allsport/Getty Images)

Tiafoe, Fritz and Paul, plus Brandon Nakashima, and Sebastian Korda were also through.

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So was Ben Shelton, who put himself through a clay-court boot camp in March and early April as part of what he says will be a long-term effort to put to rest the idea that American men can’t win on clay. Shelton is something like the antithesis of his compatriots from decades gone by: in some ways, he pays the surface no heed, but not out of disrespect. He just knows that his serve, his speed, and his athleticism can work on clay — as long as he gives in to the idea that, like a Floridian summer day at the water park, sometimes you have to slip and slide. 

Beating Hugo Gaston of France, who can make a ball dance on clay like few others, in front of a hostile crowd on Court 14 Sunday? That was a good start.

(Top photos: Tim Clayton/Corbis; Patrick Kovarik/AFP via Getty Images)