Jennifer Aniston planned a major test of trust for new lover Jim Curtis

The source also said: “Jen plans to pay close attention to how Jim reacts during their night out with Brad and Ines, as she knows this will reveal whether he can remain grounded and calm when there is so much attention and pressure on him.”

Pitt is said to be open to meeting, especially since his relationship with the Ramon has become more settled since they started dating in 2022 and moved in together last year.

“Brad is genuinely happy to see Jen in a good place,” the insider added. “He hopes the meeting feels easy and natural rather than tense, and he trusts Jen’s judgment on this.”

De Ramon, previously married to actor Paul Wesley, 43, is expected to attend the dinner and is said to be unfazed by Aniston’s presence.

“Ines doesn’t feel insecure about the situation at all,” our source added. “She wants to meet Jen in person and have a real conversation, rather than forming impressions from headlines or rumors.”

Aniston’s friends say the actress is approaching her relationship with Curtis cautiously after two divorces and public heartbreak, including her recent candid discussion about failed IVF attempts.

“Jen is taking her time and not moving too quickly,” the insider continued.

“She sees this dinner as a meaningful moment, and if Jim can handle Brad’s celebrity without being intimidated or overcompensating, she will feel confident that the relationship is truly lasting.”