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Connecting the Dating Dots: Justin Timberlake

From Boy Band to Superstar Singer, Timberlake Tries to Protect His Private Life

Martha Fry
While the man credited with "Bringing SexyBack," has had his share of high-profile romances, Justin Timberlake basically seems to operate as a one-woman (at a time) kind of guy, with a brief exception during 2002.

Here we track his comparably limited, if incomparably high-profile, love life.

Danielle Ditto 1994 - 1996

Labeled as Timberlake's first "official" girlfriend, Ditto also appears to be the only one not involved in show business. Danielle dated the future superstar when they were in their early teens.

Fergie 1996

The popular solo artist and female contributor to The Black Eyed Peas reportedly was ashamed of her relationship with the then 16-year old Timberlake (she was 23). The Duchess endured incessant teasing from her friends, including earning the moniker "Stella" (as in How Stella Got Her Groove Back) for robbing the cradle, according to ContactMusic. It was their mutual love of hip hop that held them together for a brief time, she claimed.

Veronica Finn 1996 - 1998

A former member of the now disbanded girl band innosense, Finn actually replaced original band member and future Timberlake girlfriend Britney Spears. According to NNDB, Finn reappeared in Timberlake's life in 2006, but, obviously the reunion did not last.

Britney Spears 1998 - 2002

One of the most well-known, over-reported, indiscriminately dissected teen relationships in recent memory has to be the coupling of Justin Timberlake and Britney Spears. From an exhaustive discussion of did they or didn't they to post breakup speculations on who cheated on who, the public just couldn't seem to get enough of the former Mickey Mouse Club Mousekateers, and the media was willing to oblige. Once Brit and JT were finished, Timberlake set out to have a very busy 2002.

Jenna Dewan 2002 - 2003

A back-up dancer for Timberlake's 'N Sync boy band, Dewan reportedly was one of the first to fill the void left by Britney. While US Weekly reported that Timberlake purchased a new BMW for Dewan, and she was even rumored to be moving into his home, she later claimed he was just "a really good friend" in an interview with popdirt.com. Dewan married actor Channing Tatum last year.

Janet Jackson 2002

Timberlake shared the stage with Jackson during her "wardrobe malfunction" at SuperBowl XXXVIII. Not long after, the singers were paired as a romantic couple in The New York Post, as reported at the time by ABC News. Since both stars are known for being tight-lipped about personal relationships (Jackson kept her second marriage a secret for years.), the truth may never really be known.

Alyssa Milano 2002

Buzzle.com first reported a steamy hook-up between the former Who's the Boss star and the much younger Timberlake. She was 29 at the time, he 21. By the first week of 2003, the same website was reporting Milano had established who the boss was and had kicked Timberlake to the curb. (He was purportedly still seeing Dewan and had no intention of going exclusive.)

Tatyana Ali - 2003

Will Smith's former castmate in The Fresh Prince of Bel Air, Ali, who is also an R & B singer, was briefly linked to Timberlake in 2003 by The Enquirer. While we are not disputing the report, we just make the disclaimer: consider the source.

Cameron Diaz 2003 - 2007

The 9-years older Diaz and Timberlake stood solid for quite some time considering the scrutiny their relationship was under. Eventually, personal differences took their toll and the duo called it quits in January 2007 although they are said to have remained friends, according to World of Justin. Considering their willingness to star opposite each other in the currently filming movie "Bad Teacher", I would say they still get along to some degree.

Scarlett Johannsen 2007

In April 2007, amongst much speculation that the recently unattached Timberlake had latched on to Johannsen, Fox News reported that the actress, who had appeared in a Timberlake music video, refused to acknowledge the rumors in an interview for an upcoming Seventeen magazine. Interestingly, Johannsen is quoted as saying, "If it's somebody one week, it's going to be somebody else the next week. It's either me or Jessica Biel."

Jessica Biel 2007 - Present

Soon after Johannsen's quote appeared in Seventeen, the former 7th Heaven star seemed to have nabbed a permanent position on the former boy-bander's arm. Rumors began to fly after a Golden Globe's after party in early 2007. Then, Timberlake admitted to dating "someone" to Oprah (but did not specifically name Biel), as reported by People. On the heels of numerous reports of their demise as a couple, Biel declined to dish on JT for a cover story in February's issue of Vogue magazine, citing their relationship as "the most important thing in my life." So, at least as far as she's concerned, they appear to still be together.

Rihanna - 2009

While Biel seems confident in her on-going relationship with Timberlake, several news outlets, including The Huffington Post, Star magazine, and US Weekly reported that Rihanna had slipped in through a newly formed crack in the Biel/Timberlake fabric. Since Timberlake is notorious for keeping mum about his relationships, only time will tell if this rumor has any basis in fact.

Information and date, unless otherwise noted, from www.imdb.com and Wikipedia.com.

Published by Martha Fry - Featured Contributor in Business & Finance

Martha Fry works as a freelance writer and editor. An accountant who worked at Peat, Marwick & Mitchell and Price Waterhouse, she also does financial consulting and often writes on business and personal fina...  View profile

1 Comments

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  • Valerie Ferrari3/26/2010

    Great report, Martha, I well remember the Timberlake/Spears breakup -- cry me a river. LOL!

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