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Jennifer Aniston Reportedly Has Mixed Feelings About Justin Theroux’s Recent Engagement

Kristyn Burtt
2 min read
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Jennifer Aniston and Justin Theroux have maintained a friendly relationship after they split in 2018, although those dynamics could change now that he’s engaged to Nicole Brydon Bloom. The couple announced their big news on the red carpet with a shiny four-carat ring at the Venice Film Festival, but for the Friends star, it may have been the end of a major life chapter.

The 55-year-old’s reported reaction to Theroux’s engagement might be the realization that she needed to have closure on her former marriage, according to Life & Style. “When he and Jen got married, she truly thought he was going to be her forever guy,” an insider claimed. “They were a good match, and Jen hasn’t had the easiest time letting go of what they once had.” She believed they “could possibly reconcile someday” because of their substantial friendship.

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Justin Theroux and Nicole Brydon Bloom attend a red carpet for the movie "Beetlejuice Beetlejuice" during the 81st Venice International Film Festival at  on August 28, 2024 in Venice, Italy. (Photo by Daniele Venturelli/WireImage)
Justin Theroux and Nicole Brydon Bloom attend a red carpet for the movie “Beetlejuice Beetlejuice” during the 81st Venice International Film Festival at on August 28, 2024 in Venice, Italy.

The Leftovers star has remained “protective” over his ex, recently telling The Times after she criticized vice presidential candidate J.D. Vance for his “childless cat ladies” comment. “She is still very dear to me, so, of course, yeah, I feel protective,” Theroux said. The 53-year-old actor has spoken on record several times over the years, but The Morning Show star has been more private about her second marriage. She gave some light-hearted insight into their relationship in a November 2022 story for Allure about renovating his former office on her property into a “baby cave.”

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“You can imagine he likes things black and dark,” she joked, “I lightened it up, stripped it all. He came over [the other day] and was like, ‘What the f**k did you do?’ I said, ‘I brought the light back in, buddy.’ ” She also divulged they had tried to start a family through in-vitro fertilization (IVF) treatments, but she struggled with infertility, describing it as “a challenging road.” That heartbreaking situation may also tie into her reaction to Theroux’s engagement.

“Nicole is 23 years younger than Justin and they’ll probably start a family. That hurts Jen,” the Life & Style source said. “She thinks she and Justin would probably still be married today if they’d been able to have a child together themselves.” It’s always hard to close a chapter on something and someone that you cherished and loved — and for Aniston, it’s done in the public eye.

Before you go, click here to see celebrity exes who will always be friends.

Heidi Klum, Seal
Heidi Klum, Seal

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