Judith Regan trying out bondage gear.(Bravo.com)

Judith Regan is one of the most famous (and infamous) editors in the history of book publishing (an abbreviated selection from her oeuvre, to refresh your memory: Howard Stern’s Private Parts; Jenna Jameson’s How to Make Love Like a Porn Star; and, above all, the O.J. Simpson not-memoir If I Did It). And get this: On The Millionaire Matchmaker last night, her date was with Sumner Redstone, the recently divorced octogenarian CEO of Viacom! Really! Well, no, not really. But that was who Regan told The Daily Beast‘s Lloyd Grove Patti wanted to set her up with, and we sincerely regret that it didn’t happen.

Instead, Judith Regan went on a date with a comedian who maintains a Website called boozecoma.com, the tagline of which is: “Excess drinking for a better tomorrow.” It’s important, at this point, to remind everyone of the basic law of reality show appearances: Genuinely well-known people do not make them unless they either have a point to prove or something to sell. We’re not quite sure what, if anything, Regan was trying to promote, aside from her Sirius radio show. But, as she explained in her interview with Grove, “I tried to give them as few opportunities as I could to edit it and to make me [look like] the most miserable bitch on earth.”

Basically, it worked. Regan has spent the better part of the past 30 years burnishing her reputation as a hellion—media critic Michael Wolff, her kind-of nemesis, once told a funny story about a friend who heard she got arrested, and responded, “Those poor police”—as well as a figure of outrageous fortune, the kind of woman who has a scandalous affair with disgraced former New York City police chief Bernie Kerik and comes out of it ahead. (More or less, anyway.) But next to Patti, she looked kind of sweet and well-meaning, especially in her signature bright blue blazers. (Not jackets. Blazers.) Well, next to Patti as well as Real Housewife Jill Zarin, who showed up for a minute to kiss everyone hello at a dinner party Patti seemed to be throwing to celebrate her fabulous life in New York. She was making quiche Lorraine, and between that and the blazers, it suddenly felt like 1990 all over again. It was kind of nice!

Patti came running downstairs, screaming that she was late. “I can’t be late for the queen!” she was shouting. “She will kill me even if I am her friend!” Because, remember, Judith Regan is known for being short-tempered and mean. But then there she was, sitting pleasantly at a café table, not at all upset that Patti was late. She explained that she was going to do the show because she is 56, and about to be 57, and maybe hoping to get close to someone other than the guy who kissed her cheek in some footage from a party at her Hamptons house and cooed, “Goddess! How are you?” (How was she? Wearing a bright blue caftan, that’s how.) “I’m not opposed to marriage, it’s just that I don’t want to go through another divorce,” Regan said. “It took me longer to get divorced than it did to get married.”

Patti eyed her friend. “Have you dated guys who don’t make as much money as you?” she asked, sweetly. We braced ourselves for some acknowledgment of the Kerik episode. Nada. “Of course!” Regan chirped, with a Sphinx smile. OK. Well, what kind of guy did she have in mind for herself? Two words: Bruce Vilanch. Patti was stunned. “He’s gay,” she finally said. “He’s perfect for me!” Regan responded.

Next thing we know, there he is. Bruce Vilanch! At Delmonico’s, a restaurant absolutely no one ever goes to down in the Financial District. Bruce tells it to her straight: “It’s dicks, not chicks.” Regan looks crushed. Patti swoops in with her three alternatives: An actor named Dave Lagner, a comedian named Chris Griggs, and Mr. Booze Coma, a.k.a. John McClellan. None of the three appear to know who she is, and she tells them she left book publishing not in a fiery flameball of fury and legal action following Rupert Murdoch’s decision to oust her following the O.J. book fiasco, but simply that she likes to “mix things up.” Not an untrue statement! After an awkward meal, she picks John. Patti is pleased. “The cooch doesn’t need to be sewn up,” she announces. “It just takes the right guy to let the juices flow.” Grody.

John decides to take Judy to the Museum of Sex. Regan wears another blazer. Purple, this time. Regan goes and stands in front of a bondage display, her long brown hair billowing around her padded shoulders. She grips the handles and smiles coquettishly. John is flustered. “Wow!” he tells the camera crew later. “This girl is slammin’!” They get some drinks—excess booze, remember—and then they go to dinner. Regan changes into a sheer green top. John tells her how beautiful he realized she was when he saw her standing in the bondage contraption. A normal person might be kind of offended, but not Regan. She’s tough. She looks back at him and says, “Well, you finally made eye contact with me.”

And what we appear to have before us is something unprecedented in the history of The Millionaire Matchmaker: A moment of honest-to-goodness genuine human connection. John blushes. He talks about walking around Central Park at dawn, “when it’s still a park.” (We’re not sure what it turns into later in the day, but it’s a nice line.) Regan holds him in her steady gaze. “You’re a romantic,” she says. He stops short and says he’d like to take her to the park at dawn. “We’ll get you coffee,” he says. “I’ll bring you a croissant,” she replies. (“Cwah-SAHN.”) He smiles. “Get me a danish! I like a danish.” Could it be … love?

Sadly, no. Booze Coma was live-Tweeting last night, and just as this lovely moment was passing across our screens, he wrote, “The cougar hunt is on!” Cut back to Patti’s office, where Regan showed up, now in a beige pantsuit, to thank her friend for having her on the show. Patti walks her out, then turns back to her tireless sidekicks Destin and Rachel. “Let me tell you,” Patti sighs, “those bitches were not easy.”

Earlier: She’s Back, and She’s In New York