After three and a half years together and a professional relationship prior to that, Britney Spears and her fiancé Jason Trawick have called it quits.
Spears began dating her then-agent in 2009, and since then, the couple got engaged and Trawick even became a co-conservator in the pop star's estate. But they announced late Friday (January 11) that they "mutually agreed to end their one-year engagement."
Let's take a look back at happier times for the couple:
June 2009: Trawick is Spears' agent at William Morris Endeavor Entertainment when they begin dating in the summer of 2009. They go public with their romance when they show up hand-in-hand to the 2010 Grammy Awards.
May 2010: The two decide to separate their business and personal relationships, and it is confirmed that Trawick is no longer representing Spears.
March 2011: In an interview with Ryan Seacrest, the typically private pop star opens up about her life with Jason. "We're really normal," she says. "We just like to watch movies; we work out a lot; we take walks."
April 2011: Spears gushes about life with Trawick to Us Weekly the next month. "We have such a great time together! He makes me laugh, and we are so comfortable being ourselves," she said. "Maybe [I'll marry again]. Never say never!"
May 2011: Spears tells Harper's Bazaar, "I've thought about both [marriage and kids]," saying that tying the knot with Trawick could happen "if the timing was right."
August 2011: Spears and Trawick walk the red carpet at the 2011 MTV Video Music Awards, and Britney later thanks Trawick when she takes the stage to accept her Best Pop Video Moonman for "Till the World Ends."
October 2011: The couple give fans a peek at their personal life when they play the lead roles in Britney's "Criminal" video. The video focuses on a fictional love affair between their characters, who go on a crime spree that leads to a steamy encounter. Director Chris Marrs Piliero says Trawick "killed it."
December 2011: A mysterious tweet from Spears confirms that she and Trawick are engaged.
April 2012: Trawick is granted legal control of the singer as a co-conservator, along with dad Jamie Spears, of her estate.
January 2013: Spears and Trawick announce their breakup with a statement to People: "As two mature adults, they came to the difficult decision to go their separate ways while continuing to remain friends." Trawick is no longer a co-conservator of Spears' estate, and the pop star has moved on to a new talent agency.
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