She’s said to have had a crush on him for years, and pictures of Jennifer Aniston and Jon Hamm filming for the new series of The Morning Show have been just a small indication of the chemistry between the Hollywood legends, leading to speculation that the pair could become more than just co-stars. But it’s bad news for Jen, as we’re told Jon, 51, and his long-term girlfriend and fellow actress Anna Osceola, 34, are engaged.
An insider reveals, “Anna is well aware of Jen’s crush – it was one of Hollywood’s worst kept secrets for years, even before Jen signed him up for The Morning Show.”
Rumour has it that 53-year-old Jen – who’s an executive producer on the hit Apple TV+ series, as well as its star – wanted Jon to join season three partly because of her crush on the actor. But despite Jen making no secret of her feelings, she quickly realised that Jon only had eyes for his girlfriend.
“Jon was flattered, but ultimately not tempted,” our source reveals. “He really adores Anna and knew he had to put his money where his mouth was after years of sitting on the fence and dodging any serious commitment.”
Although Jen’s had her fair share of Hollywood romances, having been married to actor Brad Pitt for five years before he infamously left her for Angelina Jolie in 2005, she’s not yet found “The One”. She married again in 2015, this time to actor Justin Theroux, but the pair split two years after tying the knot. The Friends star then threw herself into work, and her real-life friends hoped she might find love on set.
Jon first met Anna on the set of Mad Men, but they didn’t start dating until 2020, years after the show ended, and only made their red-carpet debut together at the 2022 Oscars. Our source confirms, “Anna’s a perfect fit for him. She came at a time in Jon’s life when marriage, settling down and kids sound better and better. Jon proposed to Anna because he wanted to make that happen.”
The actor has previously said that Anna made him realise that “being married” and “having kids” could offer a “new version of happiness, life [and] wellness”.
But for Jen, it’s back to embracing life as a single lady. “She’s not exactly happy about the situation but she’s sucking it up and going back to the drawing board, while trying not to beat herself up. She gave it a go, it just wasn’t meant to be. At least she doesn’t have to sit back wondering what might have happened if she hadn’t tried.”
