News Gene Simmons Dated Diana Ross, and Then He Dated Her Sister-in-Law The Kiss musician learned about the strange connection after he began dating his current wife, Shannon Tweed. By Isabel Jones Isabel Jones Instagram Twitter Isabel is an Oregon-born and Brooklyn-based writer and editor with a special interest in pop culture. InStyle's editorial guidelines Published on June 25, 2020 @ 05:24PM Pin Share Tweet Email Photo: Getty Images Who: Singer and actress Diana Ross, 76, and Kiss musician Gene Simmons, 70. How They Met: It seems the beginning of Ross and Simmons’s relationship marked the end of Simmons’s relationship with another musical legend, Cher. Simmons said his relationship with Cher “sort of ended” after the singer advised him to consult her friend (Diana Ross!) about what to get her for Christmas in 1979. In Simmons’s 2002 memoir, Kiss and Make-Up, he explained that he followed Cher’s wishes and got in touch with Ross the next time he went to N.Y.C., ultimately visiting her at her home. “I remember coming in and immediately thinking two things about her: first, that she was very sensual, and second, that she was in firm control of her career,” Simmons wrote. “While we were talking, she made me coffee, and then she offered me a piece of chocolate cake. This isn’t a euphemism. I inhaled it so quickly that she offered me a second piece, and that one went away too.” TBT: Cher and Gene Simmons Broke Up After He Went Christmas Shopping with Diana Ross They soon became friends and racquetball partners (also not a euphemism). “We didn’t think much of it, and I’m not sure that either of us had any hidden agenda, but pretty quickly it became apparent something was happening,” Simmons said. Ron Galella/Ron Galella Collection via Getty Images According to People, Cher remained friendly with both Simmons and Ross following the split and even attended a Kiss rehearsal with Ross in 1980. “She’s turned into our biggest fan,” Simmons told the outlet. Why We Loved Them: Ross and Simmons were the Romeo and Juliet of the music world (kind of) — as in, Ross’s family life made Simmons rethink his rockstar lifestyle. “I was the guy in the band who was constantly on the hunt for skirt, but here I was settling into domestic life,” Simmons wrote in his memoir. Ah, yes, choices. Though he wasn’t ready to admit it to himself, he wrote that by the time he’d begun dating Ross he “started to like the idea of having children.” “I remember walking into Diana’s home in Connecticut and feeling the love she and her three girls [Rhonda Ross Kendrick, 48, Tracee Ellis Ross, 47, and Chudney Ross, 44] shared,” he wrote. “It felt safe.” Simmons called his relationship with Ross "a combination of joys," writing, "That is, I’d like to think, everyone’s hope — that a relationship can exist on more than sexual energy, like the ability to sit and actually like being with each other." TBT: Kyle MacLachlan Said Ex-Girlfriend Linda Evangelista “Opened Up the World” to Him When They Peaked: Domestic bliss notwithstanding, Ross and Simmons were also some of the most glamorous people alive. Date nights included meeting Prince or Stevie Wonder, and N.Y.C. dinners made possible because Simmons had flown in via private jet. Also, whatever this is: Richard Corkery/NY Daily News Archive via Getty Images And, not for nothing, there’s something weirdly cool about dating someone who hides their face in public. The mystery! The intrigue! The Breakup: By 1984, Ross and Simmons had “adjusted their relationship.” Around this time, Simmons began frequenting parties at the Playboy Mansion, the Midsummer Night’s Dream parties, in particular, which he described as “big summer bashes with hundreds of girls in corsets and underwear and a select group of eligible bachelors.” It was at one of these parties that Simmons met a Playboy playmate named Shannon Tweed. Simmons told Ross about Tweed and, as he told The L.A. Times, learned “within three weeks” that his new girlfriend’s sister, Tracy Tweed, was married to his ex-girlfriend’s brother, Chico Ross. “If God and the fates have a sense of humor, that’s pretty bizarre,” Simmons said of the coincidence. Where They Are Now: After decades together, Simmons and Tweed tied the knot in 2011. They share two children: Nick Simmons, 31, and Sophie Simmons, 27. Ross expanded her family as well. In 1985 she wed Norwegian shipping magnate Arne Naess Jr., with whom she welcomed two children — Ross Naess, 32, and Evan Ross, 31 — before their split in 2000.