The Simple Life alum’s relationship with Jason Shaw made headlines in the early 2000s after the duo called off their one-year engagement in 2003.
Two years later, Hilton’s love live caused a stir once again when she announced that Paris Latsis had proposed. The duo, however, called off the impending nuptials a few months later.
The Confessions of an Heiress author didn’t give up on love and was later linked to Benji Madden, Nick Carter and Adrian Grenier. She appeared to find The One when actor Chris Zylka got down on one knee in January 2018.
“He’s even more beautiful on the inside than the out,” Hilton exclusively gushed to Us Weekly of her then-fiancé in October 2018. “He’s just such a genuine, good man and an amazing, supportive best friend. He’s everything, and it’s really rare and hard to find — especially in L.A. You can’t trust any of these guys. So it’s nice to finally find someone that I can really trust.”
The “Stars Are Blind” songstress, who had pushed back their nuptials due to busy schedules, added at the time: “We go everywhere together. It feels like we’re already married anyway, but I’m excited for next year. We’re together 24/7. We’ve never spent a night apart.”
One month later, Us confirmed that Hilton and the Leftovers alum called off their engagement.
“I just realized after time it wasn’t the right decision,” Hilton said during an appearance on The Talk in November 2018. “But I wish him the best and one day I would love to get married and have children, but for right now I’m just focused on myself and my work.”
The House of Wax star embraced the single life for a while, telling Us in September 2019 that she still planned on becoming a mother despite not having a man by her side.
“I think that having a family and children is another meaning of life. One day I would love that, but with my schedule, I just honestly don’t have time for it right now,” Hilton said at the time. “One day I will, and I’ll be the best mom.”
The “Come Alive” singer didn’t have to wait long to find her future husband. Hilton started dating Carter Reum in late 2019 and by February 2021, they were engaged. The couple tied the knot in November of that year and welcomed their first child in January 2023.
Scroll down to take a look back at all the famous men that Hilton has dated: