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.

“I didn’t have time to make dating a priority,” Gast, 57, tells me. “So I thought, ‘Why not hire somebody to do the work for me?’ It’s awkward to say, but when you date someone who’s not financially in your position, it can be a problem.”

Kelley Gast, a California spa owner who turned to Kelleher to help find her dates.

So Gast decided to give Kelleher a go. In 2008, she says, she met with one of the company’s salespeople at a “swanky” hotel in Newport Beach, California. The Kelleher saleswoman who greeted her was “gorgeous” and “looked the part,” and told her she knew of a “gentleman” who would be perfect for her. Gast signed up for a membership package costing $10,000—modest by Kelleher’s standards, given that today its packages range from $30,000 to $300,000.

Gast found her first few dates with Kelleher disappointing. “No offense,” she says, “but one of [the men they set her up with] was five-foot-three and living in somebody’s guest house.”

And then, the company connected her with a man Kelleher employees “raved about,” telling her, “He’s just the greatest guy. He’s friends with people in our office and we just love him.” So, on March 26, 2009, when this man—a successful executive in his late 40s—invited Gast to his home in Laguna Beach, she says, “I went over, because they knew him so well.”

They sat talking and drinking on his porch for while, but she says she decided to leave when he started to make sexual comments (“You have a Rabbit [vibrator], don’t you?”) that made her uncomfortable.

The man then grabbed Gast by the arm, pulled her up the stairs to his bedroom, pinned her down on his bed and digitally raped her, “forcefully” “thrusting his fingers in and out of her vagina and anus,” according to her account in an April 2009 Laguna Beach police report. “Quite frankly, it was very violent,” Gast says.

Detectives who interviewed Gast described her as “very emotional” and “crying” when she came in to the station to report the sexual assault, four days after she alleges it occurred. Before that, she had been leaving messages for her matchmaker at Kelleher describing what had happened—“I said, ‘I was raped and I need you to call me back,’” Gast tells me—but “no one from the agency had returned Gast’s phone call,” says the L.B.P.D. report.

“Such intense questions,” Kelleher-Andrews said when I first spoke to her on the phone and asked whether any of her clients had ever been sexually assaulted on a date set up by her company. “I am not personally aware of anybody that has been sexually assaulted,” she added.

Later, after I had informed her public-relations representative that I had obtained a copy of Gast’s police report, Kelleher-Andrews responded through the rep: “We acted swiftly to handle an ambiguous situation in a sensitive, compassionate, and discreet manner.”

“They never provided any counseling,” Gast tells me. “Never any referrals for women’s groups or church groups or any hotlines. I felt like I was on my own.”

Kelleher International has no contractual obligation to offer sexual assault victims support. A 2021 client contract states that the company has “no legal liability for any injury or damage to Client resulting from assault.”

“I said, ‘I was raped and I need you to call me back,’” says Kelley Gast. But “no one from [Kelleher International] had returned Gast’s phone call,” according to the police report of the incident.

The man Gast says sexually assaulted her was never arrested or charged with a crime. When police questioned him at his home, he denied Gast’s allegations and offered, unprompted, to do a polygraph test, but then stalled for the next four months, finally telling police that he would not submit to a polygraph after all, according to the L.B.P.D. report.

The police report ends with Gast continuing to assist police in trying to get the man to admit her assault on the phone, which he never did. A detective at the L.G.P.D. told me that he could not comment on this or any sexual assault report, citing victims’ privacy. When I reached out to the lead investigator on the case, now retired, she declined to comment.

I e-mailed the man Gast says sexually assaulted her, and he said that he was not a paying client of Kelleher’s in 2009, the year Gast alleges the rape occurred. Rather, he was “somewhat of a troubleshooter for [Kelleher] when they had a client who was not dating successfully from their contract,” says the L.B.P.D. report.

Kelleher-Andrews and her mother, Kelleher International founder Jill Kelleher, at the company’s Corte Madera, California, headquarters.

“When I was talking with him, he told me that they don’t have enough bachelors,” Gast says. “They called him when they needed him to provide a date.”

The man told me that he thinks he continued to be sent out on dates with Kelleher clients until 2011. Kelleher-Andrews responded to his claim by saying that a “male client” accused of sexual assault was “suspended” following the accusation, but then, “in 2011, the male client was readmitted to our system and went on more dates.”

Sound Familiar?

Gast’s story is unfortunately a familiar one in terms of the difficulties of proving rape; it’s also an increasingly familiar case of an alleged sexual assault resulting from a date arranged through the dating industry.

In 2019, Columbia Journalism Investigations did a survey of 1,200 women who have used dating platforms over the last 15 years and found that more than 30 percent of them said that they had experienced some kind of sexual assault by someone they had met through a dating app, and more than 50 percent of those experiences were rape.

Should the dating industry take sexual assault more seriously?

“They never provided any counseling. Never any referrals for women’s groups or church groups or any hotlines. I felt like I was on my own.”

When I asked Kelleher-Andrews whether people who sign up for her service receive any information or training about what to do in the event of a sexual assault by someone with whom they’re matched, she said that she was not aware of any company policy regarding assault. “I can talk to the H.R. department,” she said.

Two former Kelleher employees I spoke to said that they were not aware that Kelleher actually had an H.R. department. (Several former employees of the company interviewed for this story requested to remain anonymous.) Kelleher-Andrews responded to this through her P.R. rep: “Like many small companies, we have an executive who is designated to handle H.R. matters and serve as the company’s liaison to a topnotch U.S. employment law firm.”

One of those former Kelleher employees said that she believes that this designated executive had at one time been former Kelleher C.O.O. John Galloway, who left the company roughly two years ago. Through her rep, Kelleher-Andrews confirmed that Galloway had “had some limited involvement in H.R. matters” when he was at Kelleher.

In conversations with former employees, two of them alleged that Galloway had made “vulgar” and “inappropriate” comments to them while they were working for Kelleher International. Another said that she had heard of such comments being made by the C.O.O. “Everybody just sort of said, Oh, that’s just John,” said one of these employees.

“Familiarity did creep in from here and there,” Galloway, who lives in the San Francisco Bay Area, responded when I asked him about these claims. “But I never felt I was inappropriate in any way.”

Kelleher-Andrews told me on the phone: “I’m not aware of sexual harassment in the workplace.” Through her rep, she later said: “Mr. Galloway had a long association with Kelleher International and made valuable contributions to the success of the company.”

Matchmaker in Heaven

Kelleher-Andrews, 52, was an actress on shows such as Baywatch and Melrose Place before she achieved celebrity through matchmaking.

She can often be seen in pictures on her Twitter, where she has more than 100,000 followers, appearing at star-studded events such as this year’s Elton John AIDS Foundation Oscar-viewing party. She co-hosts, with Virgin Group billionaire Richard Branson, a yearly “leadership gathering” for “high-achievers” entitled Success to Significance on Branson’s Necker Island.

Kelleher-Andrews speaks at a “Ready for Love” panel, hosted by NBC Universal at the Beverly Hilton hotel, in Los Angeles.

Her mother, Jill Kelleher, 77, was formerly a photographer for a video dating service when she founded their matchmaking company in Greenbrae, California, in 1986.

Kelleher-Andrews joined the business in 1995. Since then, she has become a driving force in raising the company’s profile, hiring publicists who’ve gotten it coverage in glossy publications and on TV, including spots on Nightline and Entertainment Tonight. (Kelleher-Andrews has been married to Nico Andrews, reportedly a “jiujitsu champion,” for 22 years. They have three children.)

From the 80s into the early 2000s, the price of a typical Kelleher package was just a few thousand dollars. But now, clients pay up to hundreds of thousands of dollars more for “bespoke, personalized service,” Kelleher-Andrews said through her rep, the fees of which are affected by a “different scope. For example, a client who splits times between residences on different continents might want to go on dates with potential partners on each continent.”

The company had its best year ever in 2021, and is “on track to top $18 million in revenue this year,” according to the Los Angeles Times.

And yet the hefty fees don’t seem to include flawless vetting.

“Well, can you define ‘vetted’?,” Kelleher-Andrews asked when we spoke on the phone. She lives in Montecito, California, in a seven-bedroom colonial mansion, set on two acres, which the Los Angeles Times described as “opulent.” She is building new company offices nearby. “When you say ‘vetting,’ it’s a very vague thing,” she told me.

“No offense, but one of [the men Kelleher set Gast up with] was five-foot-three and living in somebody’s guest house.”

“Our vetting process is a background check,” Kelleher-Andrews said, “which basically comes back as a criminal record or whether or not they have a D.U.I. or whether or not they’re a sex offender.”

Prospective clients must also fill out and sign a questionnaire, she said, in which they attest to their marital status, among other information; however, “There’s no way for us to know for sure whether or not somebody is actually being 1,000 percent accurate,” she added.

And, apparently, not everyone is required to fill out the questionnaire. I spoke to a man in his 60s, a prominent professional in a big city, who said he “got called out of the blue by Kelleher” and was set up on a date with one of its female clients. When I asked how they knew of him, he said, “Maybe they trolled,” which he was on at the time. (Through her rep, Kelleher-Andrews said: “As a practice, we do not recruit from online platforms.”)

“I thought they would do some vetting of me,” said the man. “But they didn’t do any vetting of me, at least that I know of.”

“When you say ‘vetting,’ it’s a very vague thing.”

When I asked Kelleher-Andrews about his claim, she replied, “From his perspective, he might have been like, Yes, it was super-random. For us, it could have been a month of conversation, a week of vetting, and then we finally made that call.”

According to a former Kelleher employee, however, the company “takes what’s written on the profile as if it’s set in stone. Neither clients or free ‘participating members’ … [had] to send in their license to verify their age.” (Kelleher-Andrews said through her rep that the company does require a driver’s license and checks everyone’s ages.)

In Kelleher-speak, “clients,” or “elite members,” are paying customers, while “participating members” are those who are “matched with elite members” without paying. When I asked why some members pay and others don’t, Kelleher-Andrews said through her rep: “We won’t reveal any more detail, any more than Coca-Cola would reveal its secret recipe, but we will say this: every elite member and participating member is vetted and background checked.”

The former employee went on: “I had a client who wanted to lie that he was 10 years younger than he was. I was like, ‘You can’t lie like that.’ And he replied, ‘Why not?’”

On the Hunt

Where does Kelleher International find its men? Kelleher-Andrews told me that her company doesn’t “try to sell people memberships. We find people mostly through referrals,” she said. “We’re the largest privately owned matchmaking firm. We have 20,000 people that come to us.” She said that the company only takes 5 percent of those people. “The exclusivity is [what] we work for.”

Kelleher-Andrews and British billionaire Richard Branson, with whom she co-hosts a yearly “leadership gathering” on Branson’s private island, in the British Virgin Islands.

Providing an example of how one male client was found, Kelleher-Andrews told me of how one of her salespeople had been approached by a man in a hotel lobby. “The guy was sitting in the Ritz Carlton lobby,” in Marina Del Rey, she said. “He was eavesdropping in because it was an interesting conversation that [a Kelleher saleswoman] was having with this beautiful woman that we were signing on. He said, ‘…I’m embarrassed to say so, but I might be interested in this.’…. He was a multi-millionaire flying through from Asia,” she added.

Coincidentally, in a Yelp review of the company from 2022, “Cami C.” wrote, “One of the men I met had been recruited from a hotel lobby. The second one had been recruited [from] a bar.”

“Maybe they trolled”

One former Kelleher client I spoke to, formerly a top executive at a major corporation, was recently divorced when she signed up for the matchmaking service, hoping to find someone similarly financially well off with whom she could travel and “share [her] adventures.”

She soon discovered, however, that none of the men with whom she was matched was actually paying for the service, and none of them could afford her lifestyle. After she expressed her dissatisfaction to Kelleher about her matches, she says, she was finally paired with a man who was “everything I could want. He is handsome. He is enchanting. He has charisma. He is a gentleman.”

They started dating, sleeping together, she said, and it was “a very emotional type of relationship”—despite the fact that the guy was often unavailable, coming up with excuses that didn’t add up.

Frustrated with his unavailability, she broke up with him, and then one night did an online search and found out that he was married.

There was a long silence after she told me this. “I got a little teary,” she said.

Cupid’s Dilemma

Why is it so difficult to find successful middle-aged men who want to date successful middle-aged women? Unfortunately, that seems to be a rhetorical question.

In interviews with seven former Kelleher employees, all gave basically the same explanation.

Three generations: Tallulah Andrews, Amber Kelleher-Andrews, and Jill Kelleher.

“Men that are 50 and super-wealthy want a hot 30-to-35-year-old,” a former employee said. “They don’t want a woman in her 40s or 50s. They want a 37-year-old with a great education, a good family pedigree, and money of her own.”

“I mean, it sucks, but this is the reality,” said another former employee. “And honestly it broke my heart for some of these women.”

“The problem was that 50-year-old women are amazing women with confidence and have a lot of things going for themselves,” John Galloway told me. “But the reality of the market is guys tend to want to date younger. It was always a challenge.”

In 2013, in The New York Times, Jill Kelleher similarly described the difficulty in matching women of a certain age: “A lot of older women we don’t take,” she said. “And they’re fabulous, but it’s too hard to match them.... We need to find a system to bring in the men.”

When I asked Kelleher-Andrews about this, she responded through her rep: “I won’t get into something my mom said almost a decade ago…. We have clients from 18 to 85. We look at a number of factors…. Those factors, and our analysis, are part of the ‘secret formula’ that makes us a leader in this field.”

Meanwhile, a former employee told me that Kelleher “really needed to invest in building up their database of eligible men. We were recycling the men we had.”

“We won’t reveal any more detail, any more than Coca-Cola would reveal its secret recipe.”

In 2017, Darlene Daggett, 67, formerly a high-level executive at QVC and client of Kelleher’s, sued the company after she said she paid $150,000 to be introduced to wealthy bachelors but was instead matched with a disgraced New York Supreme Court judge and a man who fainted from a heart condition on their first date, among others.

“Kelleher’s ‘highly screened’ matches for Daggett included men who were married, mentally unstable, physically ill, pathological liars, serial Lotharios, stalkers, convicted felons, and men unwilling or unable to travel and/or the subject of professional sanctions,” wrote Daggett’s lawyer, M. Kelly Tillery, in the complaint. Kelleher settled with Daggett hours after she filed her suit in federal court in Philadelphia.

“We don’t go in and talk about Darlene Daggett,” Kelleher-Andrews said when I asked her about the case. “I mean, I can find you 1,000 ridiculous stories but I can also show you that we change lives and we’ve had babies born every single month.”

Darlene Daggett, then QVC’s president of U.S. commerce, with the writer Kelly Perdew in 2006.

“After Darlene Daggett, Kelleher would just give the angry clients their money back instead of face another public lawsuit,” a former employee claimed.

“We’ve had people that have asked for their money back and we will work with them,” Kelleher-Andrews told me. “Sometimes we give people all their money back. Sometimes we give them half of their money back. We don’t want anybody to be unhappy with the process, even if we can’t find them their match.”

But most of her clients are happy, she said, claiming that her company was responsible for “thousands of marriages.” (While she at first agreed to share data with me to back up this figure, she never provided it.)

“I just love what we do, and I love our clients and our staff so much,” Kelleher-Andrews said. “I don’t want to discourage people from trying to meet someone and think that this is actually, like, a scam or it doesn’t work.... I personally have to wake up every day knowing that I’m in charge of hundreds of people’s love lives.”

The Aftermath

As for Kelley Gast, she says that she has “lived with this event”—her alleged sexual assault—“for 13 years.” “It wasn’t just the assault, but being silenced,” she says.

In 2016, after seeing yet another positive piece about Kelleher International in a magazine, Gast says she decided that she needed to let other women know about her experience with the company. So she posted a one-star review on Yelp in which she told the story of what she claims happened to her.

After that, she says, Kelleher-Andrews contacted her, saying that she wanted to warn Gast that her name was “being compromised on a public platform with the word ‘rape’ attached to it.” Kelleher-Andrews refused to acknowledge that Gast was the former client who posted this review, but said through her rep: “In a situation like this, I believe the sensible thing to do is have a private conversation with the client to try to sort things out. Any such conversations will remain private.”

“I don’t want to discourage people from trying to meet someone and think that this is actually, like, a scam.... I personally have to wake up every day knowing that I’m in charge of hundreds of people’s love lives.”

Gast also says that, after she posted her review, a lawyer for Kelleher reached out and advised her that it was defamatory, suggesting that she amend it. (Gast did not.) When asked to comment on this claim, Kelleher-Andrews responded: “If one of our lawyers contacted an individual who posted inaccurate information on the Internet about our company, that would have been a reasonable measure.”

According to two former Kelleher employees, the company also hired a firm that deals with managing online reputations to scrub Gast’s review from Yelp and other sites where she had posted it. Kelleher-Andrews responded: “Over the years, we have retained a handful of different firms who specialize in online-reputation management.”

In a lengthy exchange with the company about Gast’s alleged sexual assault, Kelleher-Andrews claimed that “a female client,” whom she would not name as Gast, had continued to use Kelleher International’s services for two years after she was allegedly raped by a man they set her up with on a date. Gast denies ever using the service again.

“I was a broken woman, looking for love,” Gast tells me, “and like so many women, [wondering,] Will they find me the right man?”

But “I was raped,” she says. “And I just don’t think they ever understood what that means.”

Nancy Jo Sales is a journalist whose 2010 article for Vanity Fair “The Suspects Wore Louboutins” inspired The Bling Ring. She is the author of American Girls: Social Media and the Secret Lives of Teenagers and Nothing Personal: My Secret Life in the Dating App Inferno