The pop icon has been dating Jason Trawick for several years, and he is accompanying her on her Femme Fatale world tour, which wraps up in Puerto Rico on Dec. 10, 2011.
"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," a Spears family insider tells RadarOnline.com.
"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."
Britney is still under a conservatorship, so she would need a judge to formally sign off on getting hitched; however, that isn't necessary for an engagement.
"When Britney does get engaged, her father's attorneys will notify the judge in her conservatorship case. It's extremely within the realm of possibility that the conservatorship will end, and then Britney will get married. It will be a very smooth transition," the source states.
Meanwhile, Britney's family "is looking forward to the day that Jason will formally be a member of their family. Britney's mom and Jason are very close," the pal reveals.
RELATED ON WONDERWALL:
RELATED ON RADAR: