Britney Spears and Justin Timberlake had one of the most iconic celebrity relationships of the 21st century. They dated for three years and were the quintessential “it” couple during the 2000-2003 time period. Collectively they cloaked the entertainment headlines from their fashionable appearances, spotlight performance of “Gone Till The End” at the 2001 MTV Video Music Awards, and intense media attention. Their high powered relationship began after attending a school dance together in 1998. Britney revealed that Justin was her very first kiss in addition to telling the world “I love him” during an intimate interview. Justin was frequently seen in the crowd for some of Britney’s concerts and praised her as one of the most enthusiastic performers. The two seemed inseparable at the time. In 2002, after three years and a joint Crossroads movie release, the couple announced they had split. Years later, Justin famously responded to a question about their relationship in 2015, “I care about her very deeply” indicating some level of respect and admiration for the singer. The couple have since moved on and found success in their respective music and business ventures. Britney married one time and currently has two sons, while Justin has experienced tremendous success as a solo artist as well as in a business setting. The legacy of Britney and Justin’s romance will not soon be forgotten, as they were one of the most iconic couples of their generation. It is amazing to reflect back on their relationship and see how far they both have come since.