Jennifer Aniston is reportedly putting her budding romance with Jim Curtis to the test by arranging a dinner that will bring her boyfriend face-to-face with her former husband, Brad Pitt.

According to Radar Online, the 56-year-old actress is planning the dinner with Pitt, bringing along her 50-year-old hypnotherapist boyfriend.

"Jen isn't interested in separating parts of her world or acting as if Brad no longer matters. What she really wants to see is how Jim carries himself when he's face-to-face with Brad, with all their shared past and Brad's star power hanging in the air," an insider told the outlet.

Another tipster added, "If Jim can handle that situation without flinching, Jen believes it speaks volumes about his self-assurance and how much faith he has in her and their relationship."

Moreover, sources say Curtis understands that the F1 star will always be part of the Freinds alum’s past.

They added, "He's approaching the dinner with interest rather than insecurity, aware that it's not about being evaluated by Brad, but about showing he can exist easily within Jen's life as it is."

Regarding Aniston’s intentions, a confidant said, "Jen plans to pay close attention to how Jim responds on their night out with Brad and Ines, because she knows it will reveal whether he can remain grounded and composed when that level of spotlight and pressure is on him."

Meanwhile, insiders say Pitt supports the meeting and hopes it will feel “easy and natural rather than tense,” adding that he has confidence in the We're the Millers actress's judgment.

On the other hand, the Troy actor's girlfriend, Ines de Ramon, whom he has been dating since late 2022, is reportedly "not feeling insecure" about the situation and is "keen to meet Jen in person and have a real conversation, rather than forming impressions from headlines or hearsay."

For Aniston, sources say if Curtis "can deal with Brad's celebrity without becoming intimidated or overcompensating," it will reaffirm her confidence in the relationship.

Jennifer Aniston and Brad Pitt were married from July 2000 until their divorce in March 2005, while Aniston has been dating coach Jim Curtis since around July 2025.