The 39-year-old agent is expected to pop the question by the end of the year when he whisks the 29-year-old star away on holiday at the end of her Femme Fatale Tour, which concludes in Puerto Rico on December 10.
A Spears family insider recently explained: "Britney and Jason discuss marriage all the time. Britney is truly in love with Jason, and well, Jason has loved her for a very, very long time.
"Jason adores her two sons, Sean Preston and Jayden James. Jason is planning on taking Britney on a secluded getaway once the tour wraps, and it's very likely he will pop the question at that time."
If Britney ties the knot again it will be her third marriage after her wedding to childhood friend Jason Alexander in 2004, which lasted just 55 hours, and later that year she married dancer Kevin Federline, the father of her two boys, which lasted three years until their divorce in 2007.
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