Shia LaBeouf’s relationship timeline is full of big names, many of whom he was linked to while acting alongside them. Despite keeping his private life pretty hidden throughout his career, LaBeouf has occasionally opened up about his love life. The Even Stevens alum revealed he went on dates with both Rihanna and Hilary Duff, and has romanced more than one of his costars. “It never got beyond one date,” LaBeouf told Playboy in 2009 about his time with the “Umbrella” singer. “The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.” The former Disney Channel’s encounter with Duff was similar. During a 2011 interview with Details magazine, LaBeouf explained that his first and only outing with the Lizzie McGuire alum was “probably the worst date either of us have ever had.” The California native has also been linked to actresses Amber Tamblyn and Carey Mulligan throughout his career — and wooed two of his Transformers costars, Megan Fox and Isabel Lucas. “Look, you’re on the set for six months, with someone who’s rooting to be attracted to you, and you’re rooting to be attracted to them,” the Peanut Butter Falcon actor said of his time with Fox. “I never understood the separation of work and life in that situation. But the time I spent with Megan was our own thing, and I think you can see the chemistry onscreen.” Seven years later, the Teenage Mutant Ninja Turtles actress opened up about the showmance during an appearance on Watch What Happens Live. “Um, I mean, I would confirm it was romantic. I love him,” Fox told Andy Cohen in November 2018. “I’ve never been really private about that. I love him.” LaBeouf had longer-term relationships with stylist Karolyn Pho and Nymphomaniac: Vol. II costar Mia Goth. After dating for four years, Goth and LaBeouf got married in Las Vegas in October 2016. Two years later, Us Weekly confirmed in September 2018 that the pair “have filed for divorce.” The lovebirds were spotted back together in March 2020, and both were wearing wedding rings while out in L.A. Scroll down to take a look back at LaBeouf’s dating history. Hear the Us Weekly editors break down the most surprising celebrity births during the pandemic in under 2 minutes!