NEW YORK—While Cindy Sherman is among the most ubiquitous of contemporary artists, she is also among the most elusive, rarely, if ever, speaking to the press. So it’s impressive for a journalist to get an interview with her — let alone date her, fall in love with her, and capture much of the fairy tale on video. But in the late 1990s, artist and TV personality Paul Hasegawa-Overacker (known as Paul H-O) did. And if you’re curious (and how could you not be?) about what it was like, you’re in luck: H-O’s film (made with Tom Donahue) about the experience, Guest of Cindy Sherman, opens Friday in theaters in New York and Santa Fe, with engagements in other cities to follow.

In 1993, H-O and Walter Robinson, then an editor at Art in America and now editor in chief of Artnet, created the public access TV show Gallery Beat, which featured raw footage of gallery openings and on-the-fly conversations with artists, dealers, and collectors: a kind of “Beavis and Butthead go to the art world,” in Robinson’s words. It was through the show that H-O met Sherman; she thought he was cute, according to her assistant at the time, and agreed to an interview at a Metro Pictures opening of her work in June 1998. After meeting by chance a year and a half later at the Brooklyn Museum, they began a four-month series of interviews for Gallery Beat. Somewhere along the way, they started dating.

Narrated by voiceovers from H-O as well as interviews with countless art-world figures, Guest of Cindy Sherman is ostensibly about that relationship — its intimacies, its effect on H-O, and its eventual end. He came to resent living life in a supporting role and watching his identity be swallowed up by hers, going from, as he says, “the person everyone wants to talk to to the person hardly anyone wants to talk to.” The culmination of his frustration was an event at which he was seated at a table far from his girlfriend's and identified only by a name card that read “Guest of Cindy Sherman” — a story nicely complemented in the film by a similar tale from David Furnish, Elton John’s husband.

If H-O’s story is the spine of the film, Guest of Cindy Sherman is most valuable, and interesting, for its candid and largely unedited look at the art world. H-O’s camera, both for Gallery Beat and later when he struck out on his own, captures moments and events that will thrill any art nerd: a brusque encounter with Tracey Emin and Jay Jopling at the Gramercy Art Fair in 1995, before the YBAs were the celebrities they are today; firsthand footage of installations by then-up-and-coming artists Spencer Tunick and Vanessa Beecroft from that same year; a snippy Julian Schnabel telling H-O and Robinson that their program is “a masturbatory exercise in stupidity”; and a hilariously frantic phone call with a Gagosian Gallery publicist as H-O negotiates, and eventually turns down, an interview with Damien Hirst (“I worked very hard to get you time with Damien,” she whines. “He postponed dinner with Madonna.”).

But the most priceless footage is undoubtedly that of Sherman. The film shows Cindy Sherman the artist: her studio, her thoughts on her art, her working process (a sequence in which she does a photo shoot of herself, applying makeup and changing poses along the way, is mesmerizing); as well as Cindy Sherman the person: visiting her sister’s home (where an angsty oil portrait that she painted when she was 17 hangs prominently), cracking jokes, flirting with H-O, even surfing (he taught her).

H-O says that Sherman was involved with and supportive of the project at the start, but has since washed her hands of it, which seems a shame. Although no one likes to see herself through an ex's lens, she comes off as funny, intelligent, warm, and approachable. In fact, the movie made at least one writer really want to hang out with her — if I could just get that interview.