View gallery Image Credit: Getty Images Lindsey Vonn is an accomplished athlete. In addition to winning four World Cup overall championships and her return to the slopes at the 2026 Olympics, she's also had a vast romantic history, dating fellow athletes as well as entertainment industry figures. Below, we break down Lindsey's loves, from her ex-boyfriend, Diego Osorio, to one of her most famous suitors, Tiger Woods. Diego Osorio Diego Osorio at the 'Jungle Cruise' premiere (Shutterstock). Lindsey was linked to tequila company Lobos 1707 founder and actor Diego Osorio from 2021 to around 2025.