Who Has Sam Milby Dated? Full Relationship Timeline EXPLAINED

Sam Milby has always been one of the Philippines’ most talked-about leading men, but beyond his successful career, his love life has kept fans endlessly curious. Over the years, he’s been linked to fellow stars, beauty queens, and even international artists, creating a timeline of relationships that reads almost like a teleserye on its own.

His story begins long before fame, with his first crush on Laura Miller at age twelve, and his first real love, Lindsay Perry, a high school romance that lasted four years on and off. But once he entered showbiz, private love stories turned into public headlines. His early years after Pinoy Big Brother immediately drew attention, with rumors linking him to actress Bangs Garcia in 2005–2006, and even a controversial whisper in 2007 about fellow heartthrob Piolo Pascual.

Soon, Sam’s first major public romance took center stage when he dated Anne Curtis from 2006 to 2008. Their relationship made them a certified power couple, and their breakup shocked fans who thought they might last. After Anne, Sam’s love life took on an international flavor, with singer Marié Digby rumored to have been part of his story between 2010 and 2011.

By 2011, Sam was briefly linked to Kim Chiu, a top star whose pairing with him surprised many. In 2013, the rumors kept coming, this time involving Shaina Magdayao, beauty queen Ariella Arida, and rising actress Jessy Mendiola, each connection stirring headlines even if short-lived.

Then came one of his most stable chapters with Mari Jasmine, whom he dated from 2015 to 2018. Fans saw a more grounded side of Sam during this time, but when that relationship ended, the attention soon shifted to what would become his most high-profile love story: Catriona Gray.

In 2020, Sam confirmed he was dating the Miss Universe 2018 titleholder, and fans immediately celebrated the fairytale pairing. By February 2023, they were engaged, and it seemed like Sam had finally found “the one.” But in early 2025, news broke that Sam and Catriona had split, shocking fans who had been rooting for them since day one.

Sam Milby’s dating history reveals not just the women he has loved or been linked to, but also the challenges of navigating relationships under the spotlight. From first crushes to a broken engagement, his journey shows a man unafraid to risk his heart, even when the world is watching.

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