Jonah Hill’s Dating History Through the Years: Rita Ora, Olivia Millar and More

While Jonah Hill has kept his personal life quiet throughout the years in the spotlight, he has notably been linked to several women, whether it was a brief dalliance or a long-term relationship.

“I've had to wait out for people to break up so I can go after a girl that I like,” he opened up to Seventeen magazine in June 2010. “If it's the right person and you really love them and you feel like it's right and you believe you're supposed to be together — you can wait it out.”

At the time, Hill was linked to ex Jordan Klein, whom he first met while they were in high school, before they went on to date for three years.

“I have a pretty serious girlfriend so I really don't think that much about dating anymore,” he told the outlet that June. “I really love her a lot and there's really nothing she can do to deter me from being with her.”

He later revealed his best dating advice: “I think honestly that you need to look for a really genuine person who is thoughtful — I think that is the most important quality in somebody. And, they also should be sensitive to other people's feelings besides their own and not super selfish. Really, you just need to click and care about each other equally.”

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Following their split, Hill’s romanced the likes of Rita Ora, Alana Haim and former fiancée Gianna Santos before confirming his romance with surfer Sarah Brady in October 2021.

“Grateful for you @Sarahhbrady,” the Don’t Look Up actor captioned a selfie of the pair on the beach via Instagram, alongside a red heart emoji.

Brady, for her part, also shared several loved-up snaps of the happy couple via her social media. In one August 2021 post, she called him her "person," writing, “Grateful for you each and every day with you @jonahhill.”

Hill and Brady made their red carpet debut at the premiere of the Don’t Look Up in December 2021. Two months later, he shut down engagement rumors in a since-deleted Instagram post. “The rumors are true,” he wrote, before joking, “I’m engaged. But not to my girlfriend. I am engaged to your mom. I know this is shocking but please respect our privacy at this time.” It is unknown exactly when the couple called it quits, but Hill was spotted with girlfriend Olivia Millar for the first time in August 2022. The You People star and the Chasseresse co-owner were seen kissing and holding hands while spending a day at the beach

Regardless of his romantic status, Hill has previously asserted that his main goal in life is to be content and fulfilled.

“So when you ask me what I do, I’m like, work s—t comes easy to me,” the 22 Jump Street actor told GQ Style in August 2021. “… I want to be happy. I literally want to be happy. That is the mission of my life, that I work hard at.”

Scroll below to see Hill’s past flings and romances through the years:

The 21 Jump Street actor dated Klein for three years before Us Weekly confirmed in October 2011 that the duo called it quits. A source noted at the time that Klein “always seemed really happy and in love” with the California native before their breakup.


“[The reason for the split] was probably traveling,” the insider noted at the time. “She would always go where he was. Now that she has a stable job, she can't just pick up and leave.”

Hill dated actor Dustin Hoffman’s daughter for nine months before Us confirmed in September 2012 that the pair called it quits. The Superbad star had known Ali’s family for years after the former flames reportedly attended the same high school.

The Wolf of Wall Street actor was briefly linked to the British songstress shortly before her split from Rob Kardashian. At the time, Kardashian alleged via Twitter that the “Your Song” crooner was unfaithful. A source told Us in December 2012 that Kardashian dumped the Masked Singer UK alum after learning she cheated on him with the Accepted actor.

Hill was briefly linked with the Haim musician in 2014 before the duo ended their relationship that August.

Us exclusively confirmed in January 2014 that the Moneyball star was seeing McNally after they were first spotted together months earlier while walking their dogs.

Hill dated the nutritionist in spring 2014 after they were first photographed together that April. One month later, the duo packed on the PDA while lounging in the park.

After dating for nearly one year, Hill popped the question to the Violet Grey content manager in September 2019. However, the pair split in October 2020. A source exclusively told Us at the time, “The spark went [out] in Jonah and Gianna’s relationship.”

Hill confirmed his romance with the University of California, San Diego alum in September 2021, posting a selfie of the pair via Instagram. He captioned the snap, “❤️😍🥰 grateful for you @sarahhbrady.”

Brady, for her part, shared several pics with her beau on her social media, including a selfie of the couple kissing that August, writing, “My whole heart 💓." The pair eventually called it quits, though the exact timeframe or reason behind their breakup is unknown.

Hill was spotted with the vintage shop owner in August 2022. The two were seen kissing and holding hands during an outing at a beach in Santa Barbara, California. In March 2023, the couple sparked engagement rumors when Millar was photographed wearing a diamond ring.