REG JONES: "It seemed like the happiest time of our lives," Spears' high school sweatheart Jones (now 29) told Us. The pair dated for three years and he claims they slept together long before her statements about waiting for marriage. "We even talked about marriage," Jones said. "Then all of a sudden, she went on to stardom and I was pushed away without any reason why."
The prince and princess of pop met as young stars of the Mickey Mouse Club and dated for four years, ending in 2002. "I've only slept with one person my whole life. I thought he was the one. But I was wrong," Spears told W of their relationship.
Spears' four-year relationship with Timberlake ended after rumors surfaced that she and Robson, her former choreographer, had an affair in 2001. Timberlake's "Cry Me a River" video is assumed to be based on that allegation.
The actor was seen making out with the singer in January 2003 after the premiere of his movie The Recruit. "I haven't had a boy in a really long time, and I'm really craving," Spears told W a few months later. "Just a kiss would be nice."
The Limp Bizkit frontman admitted in February 2003 that he and Spears dated for "a little while" when he produced some songs for her. He told Howard Stern she seduced him in the studio one night by showing up in a "see-through shirt with no bra" and later invited him back to her house. Spears denied the fling, telling MTV, "He's not my type."
Revenge romance? Spears went on a date with the My So-Called Life actor in August 2003. Leto's ex, Cameron Diaz, was dating Spears' ex, Justin Timberlake, at the time.
Spears shared a bed with Short, a choreographer on her In the Zone tour, in the summer of 2003. "We never had sex because another person was in the room at the time," he has said. "The chemistry was magical... our feelings were so strong." The tryst derailed his marriage.
Spears flew her childhood chum to Las Vegas for a surprise wedding in January 2004. The marriage lasted 55 hours before it was annulled. "I am really worried that she will end up like Anna Nicole Smith and be found dead," Alexander told The Mirror later.
They were first linked in April 2004. At the time, Federline's then-girlfriend, Moesha actress Shar Jackson, was six-months pregnant with their second child. Spears wed Federline that September but they split in November 2006. He now has sole physical and legal custody of their two boys, Sean Preston and Jayden James.
Spears was linked to her former producer in December 2006. In November 2007, In Touch Weekly wrongly claimed Spears was pregnant with his child.
Spears dated the model, 26, for a month in January 2007. "There was no big drama," his pal told Us of their split. "It was never more than just hooking up."
Rumors swirled that Shippen was more than the "manny" to Spears' children, whom he looked after during the summer of 2007.
The singer spent five hours with the 21-year-old college student in August 2007 after filming part of her "Gimme More" video. After an alcohol-infused game of Truth or Dare and a dip in a hotel hot tub, the pair started making out. "I turned around and saw that she was topless and she had fake tattoos of flowers on her nipples," he told Us.
had at least three sleepovers with the illusionist, 39, in August 2007 while they prepared for her ill-fated Video Music Awards comeback performance, an insider said. "Criss is a total dog," his pal told Us. "He knows that Britney is susceptible at the moment and is going for it."
Before Jessica Simpson scored the Dallas Cowboys quarterback, Spears gave him a lap dance in October 2007 at Hollywood club Les Deux. Though Spears and Romo denied hooking up, Ryan Seacrest claimed he witnessed it. "I believe I saw her and Tony Romo frolicking," he said on his radio show.
Spears spent some alone time with the married, 35-year-old paparazzo in December and January after he wooed her by taking on a protective role. "I think she's a great person," he told 20/20. "It's unfortunate that she's the way she is, because of the people she surrounds herself with." A day after she left Cedars-Sinai January 5, she ran away with him to Palm Desert.