‘The Challenge’: Get to Know Sydney Segal’s Fiancé Anthony D’Alessandro
Sydney Segal is back for another season of The Challenge. After making her debut on Season 41 last year and finishing in second place, Sydney is undoubtedly a force to be reckoned with … and she knows it.
And while Season 42 has been filled with house hookups and flirty showmances, Sydney is laser-focused on the game. The Survivor alum has a fiancé at home. She has been engaged to Anthony D’Alessandro since earlier this year.
“Queen, Esquire, God’s Gift, but above all else, the best title is Fiancée,” Sydney captioned a January 2026 Instagram post of her future husband’s proposal. Anthony popped the question on a snowy day in New York City.
Below, we rounded up everything to know about Anthony and his relationship with Sydney. Scroll down for more.
What does Anthony D’Alessandro do for a living?
Anthony is a senior consultant at Akela, LLC, a CPA firm. He has held the position since January 2025, according to LinkedIn.
Prior to that, Anthony worked as a financial services consultant for Guidehouse from 2022 to 2024. He graduated from Ohio State University in 2022 with a degree in finance and public affairs.
“Anthony is passionate about solving complex problems and has a proven track record of delivering innovative, impactful solutions for federal government and top financial services industry clients,” per Akela.
When is Sydney Segal getting married?
Sydney and Anthony’s wedding is coming up on November 13, 2026, per their online wedding registry.
How did Sydney Segal and Anthony D’Alessandro meet?
While it’s unclear exactly how Sydney and Anthony met, they both live in New York City. She has been there since 2013, having attended Columbia University and then Brooklyn Law School. Meanwhile, Anthony moved to the Big Apple after graduating from OSU in 2022.
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Sydney and Anthony started posting together on their social media accounts at the end of 2024, so they were seemingly together for just over a year before he popped the question in January 2026.
The Challenge, Season 42, Wednesdays, Paramount+
