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DANNY & HALLE
Back in 1989 Halle Berry was starring on the short-lived Who's the Boss? spin-off, Living Dolls – and hangin' tough with New Kid on the Block Danny Wood. The relationship didn’t last – and Berry went on to marry baseball player David Justice in 1992.
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J.C. & TARA
'N Sync's J.C. Chasez had a brief dalliance with party girl Tara Reid in 2002, and even cast her as his love interest in the music video for "Blowin' Me Up (With Her Love)." "The chemistry between the two of them is dynamic," video director Bryan Barber said of the pair. But Miss American Pie didn't blow him up with her love for long – by 2005, he was linked to a pre-Tony Parker Eva Longoria.
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NICK & PARIS
Though he had her name tattooed on his wrist, Backstreet Boy Nick Carter had an infamously stormy relationship with celebutante Paris Hilton in 2004. "Our relationship totally was based on distrust. She didn't trust me. I didn't trust her," Carter said after their split. Carter – who has also been linked to Willa Ford and Ashlee Simpson – later covered up his Paris tattoo with a skull and crossbones.
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JON & TIFFANY
Jonathan Knight dated '80s pop singer Tiffany when she toured with New Kids on the Block in 1988 and 1989. More than two decades later, Tiffany accidentally outed Knight during a 2011 TV interview when asked if she'd ever dated a member of NKOTB. "The quiet one. The shy one. He became gay later. I didn't do it! But he's fabulous," she said. "Looking back when we were dating he was so much fun – we used to do facials together, he was so easy to talk to."
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JOEY & SUCHIN
It was a below-the-radar romance, but New Kid Joey McIntyre was often seen squiring MTV host SuChin Pak on one arm in 2000. Since then he's gotten married and had three kids with real-estate agent Barrett Williams.
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LANCE & DANIELLE
From 1999 to 2000, 'N Sync singer Lance Bass dated Boy Meets World star Danielle Fishel. "It was more like a kissing, high school-style relationship," Fishel said about her romance with Bass, who came out in 2006.
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JUSTIN & BRITNEY
They were pop music's Brangelina, when then-wholesome Britney Spears was inseparable from dashing 'N Sync frontman (and fellow former Mousketeer) Justin Timberlake. They even talked publicly of wedding bells! "Justin is everything, and what more could you want in a person?" Spears said. But the duo had a very public breakup in 2002, and now they're engaged – to other people.
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RICH & LOVE
The late Rich Cronin of '90s boy band LFO couldn’t believe his luck when actress Jennifer Love Hewitt gave him her number at an awards show in 1999. The couple soon embarked on a passion-filled romance, and she starred in an LFO music video, "Girl on TV." Cronin was also taken by surprise when Hewitt abruptly broke up with him in 2000: "She would say, 'I love you so much, we are never going to break up.' When she dumped me, I was like, 'What?'" he said nearly a decade later.
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NICK & MILEY
It was puppy love at first sight for Nick Jonas and Miley Cyrus when the pop stars began their two-year relationship in 2005. "He was on a quest to meet me …. And I was like, 'Oh, my gosh, I like you so much,'" Cyrus said of their instant connection. But after the breakup, Cyrus belted out a song about her ex's faults and ripped up photos of him at concerts. Jonas, meanwhile, moved on to another Disney star – Selena Gomez, before she hooked up with Justin Bieber.
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JOE & TAYLOR
Joe Jonas reminded the world why it's always a good idea to date outside your professional circle when he ended his four-month relationship in 2008 with sometime collaborator Taylor Swift. She wrote a song about their split, seemingly trashing his new girlfriend, actress Camilla Belle, and publicly mocking Jonas for breaking up with her by phone.
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NICK & JESSICA
Nick Lachey of 98 Degrees met 18-year-old future wife Jessica Simpson in 1998 at the Hollywood Christmas Parade, where "something just clicked," Simpson said at the time. For Lachey, that clicking was felt below the belt: "I saw her in red leather pants, and remember my first impression was how good her butt looked in them," he said. Four years later, the couple tied the knot, then, following hallowed Hollywood tradition, had a reality show before splitting in 2005.