Photo Credit: Michael Kovac/Getty Images for ELLE

Jennifer Aniston‘s holiday with boyfriend, Jim Curtis, could include an engagement. The couple has been dating for quite some time and is reportedly going to spend the holidays together on a trip. Now, an industry insider has claimed that some sources told him that Aniston might return with a ring on her finger.

Jennifer Aniston’s friends believe an engagement is imminent, claims source

Jennifer Aniston was first confirmed to be dating Jim Curtis in July 2025, and the couple went Instagram official in November. That same month, the duo made their first red carpet appearance at ELLE’s Women in Hollywood event. On December 13, a source told PEOPLE that Aniston will spend the holidays with Curtis, and they have even booked a “trip to the snow”.

Days later, industry insider Rob Shuter took to his Substack to share that some sources believe Aniston will be engaged to Curtis by the end of their holiday. A close friend told Shuter, “They’re not kids, and they’re not wasting time. Everyone around them is expecting a proposal.”

Many sources also told Shuter that spending Christmas and New Year’s together is a big step for the couple. One insider told the “Naughty but Nice” podcast host, “This is serious. Jen doesn’t do holiday trips unless she sees a future.”

Meanwhile, another source said, “Jim is all in. He’s not intimidated by her fame or her history. He’s calm, confident, and very present.” Curtis is said to be equally committed to his relationship with Aniston and is aware of everyone’s expectations.

Some insiders have also insisted that this is a grown-up relationship and not a fling. One individual explained, “They’ve both lived. They’ve been married, divorced, heartbroken. This isn’t infatuation — it’s alignment.” While an engagement is not confirmed, close friends of the couple believe that the timing of the holiday feels meaningful.