December 1992: Britney Spears and Justin Timberlake Met as Cast Members on the All New Mickey Mouse Club

Timberlake and Spears Began Their Individual Tenures on the All New Mickey Mouse Club with the 1993 Season and Were Part of the Show Through 1994. They First Met in December 1992 When They Were Cast. Timberlake Told Gq in 2006, “I Was Infatuated with Her from the Moment I Saw Her. ”

Billy Ray Cyrus and Firerose’s ‘Ethereal’ Wedding – but Did Miley Cyrus Go?

The Former Mouseketeers Reunited in 1998 When Spears Opened for Timberlake’s Group Nsync on the Second Leg of Their Nsync in Concert Tour, Which Ran from Late 1998 to 1999. Spears Was Supporting Her Debut Single “ … Baby One More Time” and Her Upcoming Album of the Same Name, Released in January 1999.

1998: Spears and Timberlake Reunited on Tour

The Former Mouseketeers Reunited in 1998 When Spears Opened for Timberlake’s Group Nsync on the Second Leg of Their Nsync in Concert Tour, Which Ran from Late 1998 to 1999. Spears Was Supporting Her Debut Single “ … Baby One More Time” and Her Upcoming Album of the Same Name, Released in January 1999.

1999: Timberlake and Spears Began Dating, but Denied It in the Press

Rumours Began to Swirl That Spears and Timberlake Were Dating in 1999, but She Denied It in One of Her First Interviews with Rolling Stone. “Overseas They Say It’s Nick Carter of Backstreet Boys, ” She Said of Dating Rumours About Her. “I Have No Feelings at All. ”

January 8, 2001: Spears and Timberlake Famously Wore Matching Denim Outfits at the American Music Awards

What Happened to David Beckham’s Alleged Mistress, Rebecca Loos?

Timberlake’s Band, Nsync, Co-Headlined the Show with Aerosmith. After Performing Some of Their Hits, the Bands Brought Spears, Nelly and Mary J. Blige on Stage with Them to Sing the Aerosmith Hit “Walk This Way. ”

January 28, 2001: the Couple Performed Together During the Super Bowl Halftime Show

Timberlake’s Band, Nsync, Co-Headlined the Show with Aerosmith. After Performing Some of Their Hits, the Bands Brought Spears, Nelly and Mary J. Blige on Stage with Them to Sing the Aerosmith Hit “Walk This Way. ”

February 2, 2002: Spears Debunked Engagement Rumours After Timberlake Made a Cameo During Her Saturday Night Live Monologue

During Spears’ Opening Monologue on the Sketch Show, Timberlake Showed up and Made a Surprise Appearance. While Discussing Her Time on Snl – Her Second as Both Musical Guest and Host – with Katie Couric a Few Days Later, Spears Stated That It Was “Fun” and She Was Less Nervous Than She Had Been the First Time. She Also Denied Reports That She and Timberlake Were Engaged.

February 11, 2002: Timberlake and Spears Made One of Their Last Red Carpet Appearances Before Their Break-Up

The Couple Were Photographed Holding Hands and Appearing to Be in Good Spirits at the Los Angeles Premiere of Spears’ Acting Debut in the Teen Comedy-Drama Crossroads. the Pair Also Walked the Red Carpet at Clive Davis’ Pre-Grammys Party on February 26, Before Spears Dropped the Bombshell News That They Had Split Up.

Chris Evans and Alba Baptista’s Relationship, from Rumours to Marriage

Spears Told Reporters That She Was “Not in an Intense Relationship with Anyone at the Moment” During a Press Conference for Crossroads in London, Reported Entertainment Weekly at the Time.

March 25, 2002: Spears Confirmed That She and Timberlake Had Split up After Three Year's Together

Spears Told Reporters That She Was “Not in an Intense Relationship with Anyone at the Moment” During a Press Conference for Crossroads in London, Reported Entertainment Weekly at the Time.

November 4, 2002: Timberlake Sat Down for an Interview with Barbara Walters and Addressed the Split

In the Run-up to the Release of His First Solo Album Justified, Timberlake Was Asked Repeatedly About the Split. in June, He Told People That It Had Left Him with a “Broken Heart” and Five Months Later He Sat Down with Barbara Walters for a 20/20 Interview.

November 25, 2002: Timberlake Released the Music Video for “Cry Me a River” Which Led to Speculation That Spears Had Cheated on Him

Just a Few Weeks After His Conversation with Walters, Timberlake Released the Second Single “Cry Me a River” from His Debut Album Justified. Both the Song’s Lyrics and the Music Video – Which Featured a Spears Lookalike – Reference Someone Being Unfaithful in a Relationship.

Ariana Grande and Dalton Gomez’s Split: What Happened and Where Are They Now?

“He’s Going on Television and Pretty Much Said You Broke His Heart. You Did Something That Caused Him So Much Pain, So Much Suffering. What Did You Do? ” Sawyer Grilled Spears on an Episode of Primetime. “He Left the Impression That You Weren’t Faithful, That You Betrayed the Relationship, ” Sawyer Continued.

November 13, 2003: Spears Spoke to Diane Sawyer About the Break-Up

“He’s Going on Television and Pretty Much Said You Broke His Heart. You Did Something That Caused Him So Much Pain, So Much Suffering. What Did You Do? ” Sawyer Grilled Spears on an Episode of Primetime. “He Left the Impression That You Weren’t Faithful, That You Betrayed the Relationship, ” Sawyer Continued.

May 10, 2004: Spears Released the Music Video for “Everytime” Which Fans Interpreted as a Response to “Cry Me a River”

The Lyrics to the Song Include: “I May Have Made It Rain / Please, Forgive Me / My Weakness Caused You Pain / and This Song’s My Sorry. ”

July 25, 2006: Timberlake Blamed Spears for the Post-Break-up Media Frenzy

While Promoting His 2006 Album Futuresex/Lovesounds, Timberlake Told Gq That “Cry Me a River” Was Indeed About Spears and Blamed Spears for How She Handled the Break-Up. the New Album Featured “What Goes Around … Comes Around”, a Song About Karma That Some Critics Interpreted to Be About Spears and a Sequel to “Cry Me a River”.

Will Smith and Jada Pinkett Smith’s Controversial Relationship – a Timeline

Fifteen Year's After Timberlake’s Success with Futuresex/Lovesounds, He Issued a Public Apology to Spears After Receiving Backlash Following the Release of the New York Times Documentary Framing Britney Spears. the Docu Examined the Toll Fame and Invasive Media Attention Took on Spears’ Life and Career.

February 12, 2021: Timberlake Issued a Public Apology to Spears After Facing Renewed Scrutiny in the Wake of Framing Britney Spears

Fifteen Year's After Timberlake’s Success with Futuresex/Lovesounds, He Issued a Public Apology to Spears After Receiving Backlash Following the Release of the New York Times Documentary Framing Britney Spears. the Docu Examined the Toll Fame and Invasive Media Attention Took on Spears’ Life and Career.

June 24, 2021: Timberlake Publicly Supported Spears During Her Court Battle to End Her Conservatorship

In a Series of Follow-up Posts, He Said: “No One Should Ever Be Held Against Their Will … or Ever Have to Ask Permission to Access Everything They’ve Worked So Hard For. ”

All Grown up! Where Are Britney Spears’ Sons Sean and Jayden in 2023?

In an Excerpt from the Woman in Me, the Singer’s Upcoming Memoir, Spears Says She Had the Abortion Because Timberlake Wasn’t Ready for Fatherhood. “It Was a Surprise, but for Me, It Wasn’t a Tragedy. I Loved Justin So Much. I Always Expected Us to Have a Family Together One Day. This Would Just Be Much Earlier Than I’d Anticipated, ” Spears Writes.

October 17, 2023: Spears Reveals in Her Memoir That She Had an Abortion While Dating Timberlake

In an Excerpt from the Woman in Me, the Singer’s Upcoming Memoir, Spears Says She Had the Abortion Because Timberlake Wasn’t Ready for Fatherhood. “It Was a Surprise, but for Me, It Wasn’t a Tragedy. I Loved Justin So Much. I Always Expected Us to Have a Family Together One Day. This Would Just Be Much Earlier Than I’d Anticipated, ” Spears Writes.

Britney Spears and Justin Timberlake’s Relationship, from Meeting as Child Stars on the Mickey Mouse Club to Going Public at the Mtv Vmas, to Conservatorship Support and the Recent Abortion Reveal

By Elena Rostova

• Oct 8, 2026 • 9 min read

Britney Spears and Justin Timberlake’s Relationship, from Meeting as Child Stars on the Mickey Mouse Club to Going Public at the Mtv Vmas, to Conservatorship Support and the Recent Abortion Reveal

Direct Answer • Key Takeaway

Here’s a Refresher of Their History, Which Began When They Met as Castmates on the All New Mickey Mouse Club in the Early 1990S.

Elena Rostova

Lead Health, Wellness & Medical Journalist

Elena Rostova holds a Master's degree in Public Health Journalism. She covers groundbreaking medical research, holistic wellness trends, mental health awareness, and nutritional science.

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