He's dated her, he's been her confidant. He's been her agent, and even starred in a sexy Britney Spears music video. Jason Trawick is clearly here to stay.
So when will he put a ring on it?
After dating the singer for several years, Trawick is reportedly planning to propose to the pop star once her tour concludes in Puerto Rico on December 10.
She also turns 30 on December 2, another rumored date for their engagement, which sources close to the pair say is inevitable and years in the making.
"Britney and Jason discuss marriage all the time. Britney is truly in love with Jason, and well, Jason has loved her for a very long time,” a Spears family insider says.
Jason Trawick "adores her two sons, Sean Preston and Jayden James, and they are crazy about him. Jason is planning on taking Britney on a secluded getaway once the tour is wrapped, and it's very likely he will pop the question at that time.”
Legally, Britney would need her father's legal sign-off to get hitched, given that he's still the conservator of her affairs. An engagement doesn't require that, though.
Also, it's likely that her engagement would mark a natural end to the conversatorship that's been in place since 2008. Jamie Spears trusts Jason, and Britney.
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," a pal reveals.
Here's hoping! Fingers crossed.