Two early teen romances, first to a school sweetheart and then to aspiring pop singer Veronica Finn predated intense media interest, but both ended unhappily. Timberlake then entered a high-profile celebrity relationship with fellow pop singer Britney Spears, with whom he had worked on the New Mickey Mouse Club. This ended abruptly in March 2002, amidst tabloid press speculation on Spears' infidelity with choreographer Wade Robson, a mutual friend of Spears and Timberlake. Lynn Harless says as a mother she too was devastated regarding the break-up, but to this day speaks warmly of Spears, "Britney grew up on my living room floor. I still love her to death. They (Justin and Britney) were together 10 or 11 years and had, from day one, instant chemistry between them. She's a sweet girl. I just hate what she's going through now." The breakup influenced the lyrics and theme of Timberlake's hit "Cry Me A River", one of the most popular singles from Justified.

Post-Spears, Timberlak