Sinitta and Brad Pitt had an encounter in 1987.. About. Sinitta is a 56 year old American Singer. Born Sinitta Renet Malone on 19 ober, 1963 in Seattle, Washington, USA, she is famous for e single So Macho, Grease Is e Word, Big Bro er's Bit on e . 01, · After she split up wi Simon Cowell in e 80s, Sinitta began dating Brad Pitt - and ey went on to enjoy a two-year relationship. According to e X Factor regular, 52, Brad got his agent. Apr 22, · Sinitta has revealed all e details on her two-year relationship wi Brad Pitt, confessing she spent a fortune phoning and faxing him as ere was no . Sinitta breaks down e trouble she had dating Simon Cowell and Brad Pitt Sinitta has shared a few intimate details about her on-off relationship wi Simon Cowell why herself and Brad Pitt could stay toge er. e singer was one of e biggest stars of e 1980s wi hits including So Macho and Right Back Where We Started From. 31, · She welcomed e twins, Knox and Vivienne, in 2008. After years of dating, Pitt proposed to Jolie in April , and e two wed in secret in ust . However, by . 6. Sinitta and Brad Pitt. You know Sinitta for her pop hit 'So Macho' and numerous (and hilarious) appearances on e 'X Factor', but before she famously began dating Simon Cowell in e 80's. 21, · In what is possibly e most bizarre romance in Hollywood history, Brad began dating Sinitta in e e late 1980s. During her time on I'm a Celebrity, e . 13, · e Czech model was Brad's date to e 1994 premiere of Legends of e Fall, which sent e actor's heart rob status skyrocketing—and ey were dating when Pitt . Pitt began one of his most famous relationships in 1994 when he started dating Gwyne Paltrow. e pair met while filming Se7en and got engaged in 1996. Pitt even called her e love of his life Au or: garet Abrams. Sinitta has had encounters wi Brad Pitt (1987) and Simon Cowell (1984). About. Sinitta is a 56 year old American Singer. Born Sinitta Renet Malone on 19 ober, 1963 in Seattle, Washington, USA, she is famous for e single So Macho, Grease Is e Word, Big Bro er's Bit on e Side in a career at spans 1983–present and 1975–present. Brad Pitt has had encounters wi Sienna Miller (), ia Ormond (1993) and Sinitta (1987).. Brad Pitt is rumoured to have hooked up wi Alia Shawkat (), Charlize eron (), Ella Purnell (), Kate Hudson (), Karolina Kurkova (2007), April Florio (2003) and Demi Moore (1998).. About. Brad Pitt is a 56 year old American Actor. Born William Bradley Pitt on 18 ember, 1963. 27, · Sinitta: 1986 – 1988 Brad dated Sinitta on and off for two years from 1986 to 1988. e British songstress, who also dated Simon Cowell, divulged about eir relationship on TV show I’m. Brad Pitt dated pop singer Sinitta in e 1980s. (David Redfern/Redferns) Pitt’s first high-profile celebrity romance was wi So Macho singer Sinitta in 1988. 01, · After she split up wi Simon Cowell in e 80s, Sinitta began dating Brad Pitt - and ey went on to enjoy a two-year relationship. According to e X Factor regular, 52, Brad got his agent to call hers after spotting her on TV - and it went from ere, wi e pair even attending e 1988 Smash Hits Poll Winners Party toge er. Apr 22, · As Sinitta spills details on her romances wi bo Brad Pitt and Simon Cowell in a candid new interview, here's a look back at e star's dating history. By. 18, · Shalane McCall was Brad Pitt's first onscreen kiss and ere were rumours e pair dated after meeting on e set of Dallas. It was not to be long lasting and before e season was over for e. 20, · Sinitta dated Brad during her heady pop stardays, and he even attended e 1988 Smash Hits Poll Winners Party wi her. Sharing about e split, Sinitta reported at Pitt was a lot more chilled and a bit took aback by e ings at she was doing. After Brat Pitt, she moved on and got ried to Andy Willner in April 2002. Pitt and Sinitta, a British singer known for e song So Macho and appearances on shows like I’m a Celebrity Get Me Out of Here, dated on and off for two years between 1986 and 1988.While she was on I’m a Celebrity, Sinitta talked about her short-lived romance wi e actor, who wouldn’t have his big break in elma & Louise until ree years after eir breakup. 31, · Sinitta. Between 1984 and 1986, British-American singer Sinitta and Brad Pitt dated on and off. e couple even attended e 1988 Smash Hits Poll Winners Party toge er. Shalane McCall. Shalane McCall and Brad Pitt. Image: Getty. Sinitta Malone (born 19 ober 1968), known professionally as Sinitta, is an American-born British singer, songwriter, television personality, dancer, actress and record producer. She initially found commercial success in e mid-1980s wi e single So Macho and had several o er hits during e ade.In e 2000s, she became known for television appearances, including Loose Women, e Missing: brad pitt. 29, · He has been wi e most famous and most beautiful stars in e industry. From Sinitta to Angelina Jolie to his latest alleged girlfriend, Nicole Poturalski, meet e women in e life of Brad Pitt.. Sinitta. Pitt was first linked to e British-American singer Sinitta in 1984. e en 26-year-old Brad Pitt and Christina Applegate were briefly dating in 1989, but she literally ditched him for ano er man on e night of e 1989 MTV Video Music Ads. e man in question was Sebastian Bach from Skid Row. While it was rumored at Pitt dated jewelry designer Sat Hari Khalsa for a year, and at he later allegedly dated 'Arrested Development' star Alia Shawkat, Pitt claims at all of ese rumors. Sinitta began dating Simon when she was just 14 years old and e pair were toge er on-and-off for 20 years. Simon has been in a long-term relationship wi Lauren Silverman since 2009 and e pair have a son named Eric toge er. Brad Pitt. Sinitta and Brad Pitt were an item, on-and-off, for two years between 1986 and 1988. 28, · Brad Pitt is considered one of but his handsome features and irresistible charm were already a staple in e industry dating pool long before en. In 1984, Pitt . After she split up wi Simon Cowell in e 80s, Sinitta began dating Brad Pitt – and ey went on to enjoy a two-year relationship. According to e X Factor regular, 52, Brad got his agent to call hers after spotting her on TV – and it went from ere, wi e pair even attending e 1988 Smash Hits Poll Winners Party toge er. 21, · Sometime in e late 90s, Demi Moore and Brad Pitt were rumored to have been knocking boots. e relationship was never confirmed but rumours ran wild about e two having a steamy love affair. Moore is one of e only women at Pitt dated at was at e same level of fame at he is at. 23, · Sinitta, 1984 – 1988. Bit of weird one is, but Brad honestly did date Louis Walsh's mate Sinitta on and off for four years. Fan of a palm leaf Sinitta dated Brad during her heady pop star days. Brad dated singer Sinitta between 1987 and 1988, after practically begging his agent to call hers after he saw her on TV and fell in love. Sinitta later dumped e Pitt before he shot to fame in elma & Louise but holds a sweet memory of eir time toge er. He was beautiful wi e most amazing body, she said. I saw him for two years. Sinitta from Brad Pitt's Dating History e Toy Boy singer dated Pitt off and on for several years in e '80s, long before every couple had a clever one-word nickname—so when e pop star was asked in what eir cutesy name could've been, she suggested Braditta. HE’S been e world’s most eligible bachelor on and off for ades, amid failed romances, engagements and riages to some of Hollywood’s most stunning stars. And now Brad Pitt . 16, · Brad Pitt and Angelina Jolie’s Most Memorable PDA Moments Read article Meanwhile, e Fight Club star joked about his dating life while accepting his Screen Actors Guild Ad in . 07, · Sinitta was dating Cowell when e 18-mon affair wi Es began. Mat ew McConhey gives his oughts on e 'ual tension' between Brad Pitt . A re kable actor Brad Pitt drew his first brea in Oklahoma to his parents e and Bill. His mo er was a high school counselor and his dad used to run a truck company. e celebrity also has two siblings. While studying at school, a future star loved sports, visited musical classes and was very much interested in acting. 20, · Brad has moved on from his split wi ex-wife Angelia Jolie and is now dating Oscar winner Charlize Credit: Reuters Last weekend e pair were . Apr 14, · Here’s Brad Pitt’s dating timeline: Sinitta (1984-1988)- e Toy Boy singer and Brad dated for almost four years. Yes, at’s a long time to invest in someone. Talking about Brad . , · Sinitta As Sinitta spills details on her romances wi bo Brad Pitt and Simon Cowell in a candid new interview, here's a look back at e star's dating history. Apr 27, · When Brad Pitt Was Double Dating & Got Cht Having S*x Wi Mike Tyson’s Wife Brad Pitt dated Mike Tyson’s en-wife, Robin Givens, he was already dating American-born British singer, Sinitta. 20, · Who’d have ought at Simon Cowell and Brad Pitt would have dated e same lady? e pair attended e 1988 Smash Hits Poll Winners Party toge er but e romance was short-lived, wi Sinitta. Brad Pitt is really, truly, single - and in case you haven’t heard, he’ll tell you ano er ten times. e Once Upon a Time in Hollywood star has ided to make his hot Brad summer. 26, · Brad Pitt's dating history is highly varied and very star-studded. We've rounded up every rumoured and confirmed girlfriend he's had. Sinitta: 1984 - 1986. e Toy Boy singer dated Pitt off and on for several years in e '80s, long before every couple had a clever one-word nickname—so when e pop star was asked in what eir cutesy name. More about e Sinitta and Brad Pitt dating / relationship. More about e Sinitta and Simon Cowell dating / relationship. More about e Sinitta and David Es dating / relationship. More about e Sinitta and John Fashanu dating / relationship. More about e Sinitta and Andy Willner dating / .