The 31-year-old TV producer - who has been dating the 'Piece of Me' hitmaker for two months - is expecting to pop the question in time for the pair to celebrate the engagement at a ''lavish Christmas bash'' in Costa Rica with Charlie already receiving his soon-to-be father-in-law, Jamie Spears', blessing.
A source revealed: ''Charlie pitched Jamie about casting Britney in a new reality show, and Jamie thought he was a really good guy.
''They've been moving closer at light speed, and when Charlie suggested to Jamie that he ask for Britney's hand in marriage, Jamie quickly said yes.''
However, not everyone is on board with the couple's whirlwind romance, mainly Charlie's 68-year-old mother Susan St. James.
The source continued to National Enquirer magazine: ''[Dick Ebersol] thinks it's great to see his son happy [but Susan] just doesn't think that Britney is the right choice''.
Meanwhile, Charlie recently revealed how his past helped him ''prepare'' to have a relationship with the 33-year-old singer.
He said: ''My personal life is my personal life, but I will say this: If I had not gone through what I've gone through, I would not have been prepared to be in a relationship of any kind, much less in one with someone like Britney, who has the enormous heart that she does.
''I was bullied very badly in high school. I was a very successful kid. I sold my first company at a young age. There was a lot of misplaced rage in high school towards me. My brothers and sisters identified it as bullying, but I didn't at the time. What was amazing to me was I started feeling I wasn't worthy of being loved...I ended up blocking this from my memory.''
'Smalls Change (Meditations Upon Ageing)' arrives in April.
The two awards have made for a great 72nd birthday present for the country music icon.