The 500th time won't be the charm for Betty Kai.
She's tied the knot about that many times since 1991... but not for herself.
Kai is a highly-requested officiate on Fort Myers Beach, and has helped officiate weddings since she moved to Lee County and started working on the beach.
Betty Kai has performed at least 500 weddings since 1991.
Twenty-six years ago, Kai moved from Wisconsin to the county to be closer to her son, Jeff Kai. Formerly a paralegal, she transferred her officiate license to Florida and started bartending at Jimmy B's, which was destroyed after Hurricane Charley.
One day while at work, the bar got a call from what was then the Ramada Inn for a wedding reservation and a officiate. She offered to officiate.
Word got around, and Kai has turned her officiate license into a booming side-business. That is, when she's not bartending at Lazy Daze Saloon or hostessing at Nervous Nellies, or playing Mrs. Claus during the beach holiday boat parade.
"I'm now marrying the children of people I married years ago," the 89-year-old said.
She's seen it all: beach weddings and inside weddings; traditional wedding gowns and swimsuits. She's even married a few people multiple times. But one of the funniest was a wedding where the bride and groom pulled out light sabers at the end, she said. Both of them loved Star Wars.
Another memorable finish? A wedding conducted on a parasail boat out in the Gulf. After she pronounced the bride and groom, they stripped off their clothes to reveal swim suits beneath and launched into the air.
"I look forward to the weddings - every one is different," she said.
Since the rise of the internet and creative websites like Pinterest, Kai said more and more couples are getting creative and trying out "crazy" and unusual ideas for their ceremonies. More and more, the couples are writing their own vows, too, she said.
"They want to make it their own," Kai said.
Kai officiates weddings on both an on-call basis for the local hotels and resorts as well as private weddings. Betty has a few special touches with her private weddings. When they're held on the beach, she replaces a "unity candle" ceremony with a sand ceremony, in which the couple will pour two vials of sand together into one receptacle, symbolizing the partners becoming one.
She said about 80 percent of the business goes to Lani Kai; between Oct. 2016 and now, she's already done 17 weddings and performed one on the beach at the resort this past Saturday.
Most of the time, she doesn't know the people she's marrying. But sometimes, it will be friends or friends of friends or coworkers - or even her son.
Kai married her son, Jeff, and his wife Shelly, in 2014. The two had dated back in Wisconsin for a while and separated. They stayed in touch and both happened to move back to Florida after divorcing previous spouses. They reconnected, and they both "just knew," Shelly said.
"It took 25 years and 1,200 miles," Jeff said.
Now, they also help Betty with her private weddings. Jeff will help arrange and set up the venue and Shelly will record the ceremony for the couple.
"I love hearing the stories of how they met," Shelly said.
So weddings have become the Kai family business. Betty is hoping to pass off her legacy and convince Shelly to get her officiate license, too - although Betty doesn't have any plans to quit hitching folks, yet.
"It's my goal to live to be 110, so I have some time," she said. "I'll keep it going as long as I'm able. It makes people happy."