Valentine's Day 2025

by  Amal Lattouf 

In tennis, "love" equals zero—a quirky scoring term that means you've got nothing. But for Cynthia and Tim, "love" at Four Seasons Racquet Club turned into everything.

It all started back in the summer of 2002. Tim had just moved to Fairfield County from Zimbabwe after living in Hong Kong, where his company asked him to run the U.S. office. He didn’t know a soul when he landed here, so he joined Four Seasons, hoping to find some tennis partners and maybe a social life. "I was tired of sitting on the couch watching TV alone," Tim said. "So I figured, let's give it a shot."

Enter Mike and Stephanie Pelletier, a tennis-playing couple who quickly noticed that Tim and Cynthia were, as far as they could tell, the only two single people at the club. And so, the matchmaking began.

"Stephanie was playing doubles with me," Cynthia recalled. "She casually asked if I’d like to meet someone. I said sure, why not. But I figured I’d get dressed up for it, you know? Well, nope. We met right after a sweaty match. I thought, 'Well, this is what it looks like. No point pretending otherwise.'"

Their first meeting was short and simple, but Stephanie was determined to see it through. For the next several weekends, she orchestrated doubles matches that conveniently paired Tim and Cynthia together. It worked. During one of those games, Tim found himself eavesdropping on Cynthia's conversation with another player and was immediately intrigued. "I've always liked smart women," he said. "And she casually dropped the word 'behooves' into a sentence. I thought, 'This one has potential.'"

But despite the tennis chemistry, Tim hesitated to ask Cynthia out. "He thought American women were litigious," Cynthia said with a laugh. "Like if he said the wrong thing, I'd sue him or something. I finally had to step up and ask if he wanted to get together outside of tennis."

They went to dinner at Portofino in Wilton, which later became Red Rooster. Four hours later, they'd covered everything from family to travel to the absurdity of tennis scoring. Within a year, they were married.

"Back then, Four Seasons was a big social hub," Cynthia said. "There were mixed doubles games all the time, plus parties by the pool with live music, amazing food, and a guy who'd bring his own lamp to set up by the keyboard. Stan, Greg's dad, always made sure everyone felt welcome. And it’s nice to see the club revitalizing that community feel again."

They even chose their house based on tennis proximity. "We were living in a condo," Tim said. "When we started house hunting, one rule was it couldn't be too far from the club."

Now, 21 years later, they still show up to play—sometimes together, sometimes separately, but always with the same appreciation for the sport and the community that brought them together.

"We literally said that if it's too far from Four Seasons, that's not gonna work for us," Cynthia said with a laugh.

Next time you're at Four Seasons, take a look around. You never know—you might be one well-placed word away from meeting your match, too.