Kelley Gast, the owner of a chain of luxury spas based in Costa Mesa, California, was newly separated from her husband when she saw an ad for Kelleher International in American Way, the now shuttered in-flight magazine of American Airlines. “Single, Successful, Selective … Simply Too Busy!” said the ad, seen by millions of business travelers, which featured a smiling headshot of the matchmaking service’s attractive blonde C.E.O., Amber Kelleher-Andrews.

On Google, Gast saw that Kelleher had received an enviable amount of positive media attention over the years, which has continued to this day. In 2013, The New York Times called it “the high-end matchmaking service for tycoons.” And in 2022, the Los Angeles Times described Kelleher-Andrews as “a matchmaker to the rich and famous”—reportedly including Today co-anchor Hoda Kotb, supermodel Cheryl Tiegs, and N.F.L. legend Terrell Owens.