Jennifer Aniston has been open about valuing honesty and emotional clarity, especially when it comes to relationships. Sources are claiming that she’s considering a “meaningful” next step that involves bringing together two important figures from different chapters of her life. The reported plan is said to reflect her desire to move forward without ignoring the past.
Jennifer Aniston ‘wants to see how Jim carries himself’ around Brad Pitt, per source
Sources speaking to RadarOnline allege that Jennifer Aniston is planning a joint dinner involving her boyfriend, wellness coach Jim Curtis, her ex-husband Brad Pitt, and Pitt’s current partner, Ines de Ramon. According to insiders, the dinner is intended as a kind of “trust test.” It is said to allow Aniston to observe how Curtis navigates a situation involving intense star power and emotional history.
Aniston, 56, and Pitt, 62, have maintained a friendly relationship since their 2005 divorce. Friends claim that their dynamic plays a role in how Aniston evaluates romantic partners. One source alleged that Aniston values transparency and doesn’t want to compartmentalize her life.
“What she really wants to see is how Jim carries himself when he’s face-to-face with Brad,” a source claimed. They noted that the evening would bring decades of shared history into the same room. According to the insider, Aniston is less concerned with comparison and more focused on whether Curtis appears secure, grounded, and comfortable.
Meanwhile, Curtis, 50, is said to be open to the meeting. Sources allege he understands Pitt will always be part of Aniston’s past and doesn’t view the dinner as a competition. “He’s approaching the dinner with interest rather than insecurity,” one insider claimed.
According to insiders, the rumored dinner would also include de Ramon, whom Pitt has been dating since 2022. One source claimed Pitt is open to the idea and hopeful the meeting would feel “easy and natural rather than tense.”
Friends close to Aniston suggest the actress is moving carefully after two divorces as well as years of public scrutiny. One source claimed the dinner feels “meaningful” to Aniston, adding that if Curtis handles the spotlight with ease, it could signal long-term potential.
