NEED TO KNOW
Sydney Segal announced her engagement to longtime partner Anthony D’Alessandro in an Instagram post on Sunday, Jan. 18D’Alessandro was photographed on one knee proposing to The Challenge star in New York City“Queen, Esquire, God’s Gift, but above all else, the best title is Fiancée 💗,” the pair captioned the joint post
Sydney Segal is ringing in the new year with wedding bells!
On Sunday, Jan. 18, the reality TV star, known for The Challenge and Survivor 41, announced her engagement to longtime partner Anthony D’Alessandro in a joint Instagram post. The couple shared a photo of the moment D’Alessandro got down on one knee at Pier 17 in the Financial District of Manhattan, New York City, to ask Segal, 30, to marry him.
She appeared emotional as she covered her face with one hand, while D’Alessandro looked up at her lovingly. The pair were both pictured wearing winter coats and sneakers for the outing amid the freezing temperatures and snow.
“Queen, Esquire, God’s Gift, but above all else, the best title is Fiancée 💗,” they captioned the joint post.
Sydney Segal; Anthony D’Alessandro.
Ayoleka Sodade/Instagram
D’Alessandro reposted the photo on his Instagram Stories alongside three white heart emojis accompanied by Kehlani’s song “Nights Like This.”
He then shared a snap of her smiling while holding a martini cocktail with her sparkling engagement ring in full view.
“New bling,” he captioned the photo.
The pair continued to celebrate the milestone in their relationship with a luxurious meal at Chelsea Living Room.
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Sydney Segal gets engaged to Anthony D’Alessandro.
Segal’s The Challenge costar Leka Sodade revealed she was among the first to find out the good news as she shared a screen grab from their FaceTime call on her Instagram Stories.
Sodade was all smiles as the California native held up her engagement ring to the camera with D’Alessandro alongside her.
“OMG MY FAVESSSSSS,” she wrote over the image, alongside a face holding back tears emoji, a face with love hearts and a red heart.
Before appearing on MTV’s The Challenge in 2025, Segal appeared on CBS’s Survivor in 2021.
Sydney Segal gets engaged to Anthony D’Alessandro.
She and D’Alessandro keep their relationship private but have appeared on each other’s social media since at least 2024. Among their snaps have been visits to London, Greece, Germany and the Netherlands.
Before their joint engagement announcement, Segal gushed about D’Alessandro in the caption of an Instagram post on Dec. 15.
“High value alone, unmatched together 🖤,” she wrote alongside a black and white photo of them at a party.