Hollywood is buzzing with excitement: Could Jennifer Aniston, the eternal rom-com queen turning 57 in February 2026, be heading for wedding number three? After two high-profile marriages to Brad Pitt and Justin Theroux, the 56-year-old “Friends” star seems blissfully in love with wellness coach and hypnotherapist Jim Curtis. Whispers of a secret engagement have intensified thanks to a sparkling diamond ring spotted in recent photos and their ultra-romantic holiday plans. Is this the real deal, or just holiday magic? Let’s uncover the clues that have fans on the edge of their seats.
The speculation ignited on November 2, 2025, when Aniston hard-launched her relationship on Instagram for Curtis’s 50th birthday. The black-and-white photo showed her wrapping her arms around him from behind, captioned “Happy birthday my love. Cherished ❤️.” Eagle-eyed fans immediately zoomed in on a large diamond ring on her left ring finger, sparking instant engagement rumors. Tabloids like National Enquirer and RadarOnline reported that sources close to the couple believe the ring is no ordinary accessory—it’s a sign of something bigger.
Fast-forward to December 2025, and insiders are claiming the couple’s first Christmas together could end with a proposal. According to industry expert Rob Shuter and reports from People and Reality Tea, Aniston and Curtis have planned a lavish yet intimate holiday season. They’re hosting close friends like Courteney Cox (with her partner and daughter Coco), Jason Bateman and his family at Aniston’s California mansion for a “all-out” Christmas celebration—complete with a real tree, festive decorations, and blended family vibes, including Curtis’s son Aidan.
But the real romance kicks in post-Christmas: a cozy “trip to the snow” followed by a sunny New Year’s getaway. Sources told Yahoo and Page Six that friends are “expecting a proposal” during this magical time, with one insider saying, “They’re not kids, and they’re not wasting time. Everyone around them is expecting a proposal.” Aniston, who once swore off marriage, reportedly feels “totally secure” with Curtis, describing him as a “ray of sunshine” who brings peace and positivity to her life.
Adding fuel to the fire are earlier reports of dream wedding plans in Greece—a destination deeply meaningful to both. Aniston’s late father, John Aniston, was born on Crete, and Curtis has Greek heritage. Insiders have shared visions of “sunrise vows overlooking the Aegean Sea” amid ancient ruins, keeping it intimate with just their closest circle.
Curtis, a successful author and hypnotherapist known for helping people heal trauma, met Aniston through mutual friends earlier in 2025. Their relationship evolved from friendship to romance, with public sightings in Mallorca, New York, and their red carpet debut at Elle’s 2025 Women in Hollywood event. Aniston has called him “quite extraordinary” and “very special,” praising his kindness and normalcy in a Hollywood world.
At 56, Aniston is glowing—focusing on her LolaVie brand, “The Morning Show,” and this grounded love. Fans are thrilled, flooding social media with messages like “Jen deserves this happiness!” Whether the ring is an engagement sparkler or just fabulous jewelry, and if those holiday trips lead to “I do,” one thing’s clear: This could be Aniston’s most heartfelt chapter yet.
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