When you’re as iconic as Britney Spears, it’s hard to keep your love life under wraps.
The singer had a high-profile romance with Justin Timberlake years after they met while filming The Mickey Mouse Club in the ’90s. The couple confirmed their romance in 1999 and later split in 2002. Their breakup, just like their relationship, made headlines when Timberlake released “Cry Me a River.”
In 2021, the documentary Framing Britney Spears explored how Timberlake’s behavior after their breakup led to further speculation that Spears cheated on him. Fans rushed to defend Spears’ image and called for the “Rock Your Body” singer to apologize for his part in the situation.
“I’ve seen the messages, tags, comments, and concerns and I want to respond,” Timberlake wrote in a statement via Instagram in February 2021. “I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right. I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism.”
Timberlake then apologized to Spears and Janet Jackson for the role he played in their images being affected.
“I have not been perfect in navigating all of this throughout my career. I know this apology is a first step and doesn’t absolve the past,” he continued. “I want to take accountability for my own missteps in all of this as well as be part of a world that uplifts and supports. I care deeply about the wellbeing of the people I love and have loved. I can do better and I will do better.”
At the time, a source told Us Weekly that “Britney does not hold a grudge against Justin over anything he’s said or done.”
“She feels that they were young and in love and both did stupid things when they were together. She was heartbroken when they separated, but it’s not something she dwells on now. She’s happy and happy for him,” the insider added.
Spears went on to have a number of relationships, even briefly getting married to Jason Alexander for 55 hours in 2004, before announcing her engagement to backup dancer Kevin Federline that same year. The pair got married in September 2004. They later welcomed son Sean Preston in September 2005 and Jayden in September 2006. The duo got divorced one year later.
Following her split from Federline and amid personal issues, Spears was placed under a conservatorship in February 2008.
The dancer started dating Sam Asghari after meeting on the set of her “Slumber Party” music video in 2016.
After several years together, a source confirmed to Us that the twosome were getting serious.
“Sam would love to start a family with Britney,” a source said in March 2021. “He’s always dreamt of having children and thinks he would be a great father. He’s a natural around little kids.”
The insider added that Asghari was looking forward to a serious future with Spears, who he preciously gushed about on social media.
“Sam also sees marriage in his and Britney’s future when the time is right and they are able to wed without the restraints of her conservatorship and with the blessing of her family,” the source told Us. “He’s very old-fashioned in that way.”
During her conservatorship hearing in June 2021, Spears spoke out about wanting control of her body and over the decision to expand her family.
“I want to be able to get married and have a baby,” she revealed at the time. “I was told right now in the conservatorship, I’m not able to get married or have a baby, I have an IUD inside of myself right now so I don’t get pregnant. I wanted to take the IUD out so I could start trying to have another baby. But this so-called team won’t let me go to the doctor to take it out because they don’t want me to have children — any more children.”
Scroll down for the singer’s complete dating history: