Now, one of Jim’s exes, 37-year-old wedding planner and podcaster Alyssa Pettinato, is speaking out — and she’s full of praise.
“I call him Uncle Jesse,” she joked, likening him to John Stamos’ charming Full House character. “He’s got a great face, he’s successful, he’s smart — and that draws a lot of women in.”
Alyssa and Jim briefly dated after connecting on a dating app. Their relationship only lasted a few months, but she looks back with fondness.
“We went on a few dates. He’s just a good guy. Things didn’t work out — that was on me, I kind of disappeared,” she admitted. “But he’d be an amazing partner for the right person. He gets along with almost anyone, he’s easy to talk to, low-drama. We’re still friendly, and I have nothing bad to say about him.”
Earlier this year, she even invited Jim to appear on her podcast, praising his calm demeanor, practical wisdom, and attention to detail. While he didn’t share much about his private life during the episode, the conversation centered on how men should carry themselves with dignity after breakups. “It was basically about not being a jerk when relationships end,” she explained.
Pettinato also gave her blessing to Jim’s new romance with Aniston, claiming he’s a better match than either of her ex-husbands, Brad Pitt or Justin Theroux.
“I don’t know Jennifer personally, but we have something in common — we’re both Greek,” she said. “Jim’s Greek too, and I think there’s something powerful about that cultural connection. If they’re together, I feel like the Greek bond is strong.”
Jennifer, whose father John was born in Greece, spent part of her childhood there and was raised in the Greek Orthodox tradition.
An insider close to the actress shared that she’s feeling fulfilled in her personal life but is in no rush. “Jen’s friends think Jim is perfect for her,” the source said. “They both love self-work and growth, and Jen feels Jim really gets it. She’s read almost every personal development book out there, and meeting Jim felt like something that was meant to happen.”