Jonah Hill's Extensive Dating History: From Singer, Rita Ora, To Olivia Miller, Mother Of His Child

Actor, Jonah Hill is known for making his audience laugh with his unique comedic roles. He made his debut almost two decades ago with the film, I Heart Huckabees, which was released in 2004. He had his big break when he landed one of the starring roles in the 2007 teen hit, Superbad. Since then, he never had to look back as his career skyrocketed, with him appearing in renowned films like Get Him to the Greek (2010), 21 Jump Street (2012), The Wolf of Wall Street (2013), and Don't Look Up (2021), among others.  

Recently, Jonah celebrated his 42nd birthday on December 20, 2025. With attention on him once again, many have started to wonder who his current partner is and which famous women he was previously linked to throughout his decades-long Hollywood career. If you are one of them, without further ado, let's take a look at Jonah's dating history.

Jonah Hill dated Jordan Klien, whom he met in high school

The Wolf of Wall Street actor reportedly met his ex-girlfriend, Jordan Klein, when they were still in high school. Although we don't know exactly when the two started dating, their relationship lasted for three years. The news of their breakup started to make the rounds in 2011. A source at the time revealed that Jonah "always seemed really happy and in love" with his high school sweetheart before they decided to call it quits. Speculating about the probable reason that led to their decision, the insider also noted:

"[The reason for the split] was probably travelling. She would always go where he was. Now that she has a stable job, she can't just pick up and leave."  

Jonah Hill dated Dustin Hoffman's daughter, Ali Hoffman  

After his breakup with Jordan, he moved on with Dustin Hoffman's daughter, Ali Hoffman. The couple were together for nine months and are rumoured to have broken up somewhere around September 2012. Ali is also someone Jonah knew from his high school years, since they attended the same school. This also made him pretty familiar with Ali's entire family.  

Jonah Hill dated pop star, Rita Ora 

Jonah was briefly linked with the Your Song singer, Rita Ora. The rumours of their alleged romance came just before Rita split with her then-boyfriend, Rob Kardashian. At the time, Rob furiously took to his official X (formerly Twitter) handle to declare that the singer had been unfaithful to him. According to a source for Us Weekly, Rob dumped The X Factor alum after learning that she had cheated on him with Jonah. This news broke around December 2012.  

Jonah Hill's fling with Alana Haim 

In 2014, Jonah was rumoured to be dating Haim musician, Alana Haim. However, their relationship was pretty short-lived as the two went their separate ways only a few months later in August.  

Jonah Hill dated Isabelle McNally in 2014 

According to a report by Us Weekly, Jonah was already dating popular actress, Isabelle McNally in January 2014. The couple was first photographed together when they were walking their dogs in September 2013. However, it is not known when the duo broke up.  

Jonah Hill dated Brooke Glazer in the spring of 2014 

2014 was the year of short-lived romances for Jonah Hill. In the spring of this year, the 21 Jump Street actor dated nutritionist, Brooke Glazer. While the two were photographed together in April, they were later spotted packing on the PDA in a park, a month later.  

Jonah Hill was engaged to Gianna Santos  

Jonah and Gianna Santos, a content manager for the L.A.-based beauty company, Violet Grey, were first spotted together near the end of 2018, in August. After dating for almost a year, Jonah popped the big question to Gianna in September 2019. However, they were not meant to be, as the pair called it quits a year later in October 2020. According to an insider close to the former couple, “the spark went [out] in Jonah and Gianna's relationship.”  

Jonah Hill's relationship with Sarah Brady ended in a messy breakup  

This time around, Jonah himself confirmed his relationship by taking to his Instagram in September 2021 and posting a selfie together with Sarah Brady. He captioned the picture, “grateful for you @sarahhbrady,” followed by a bunch of emojis, including a red heart. Despite having what appeared to be a strong relationship on the outside, the two decided to break up, although the exact timeframe is unknown. One thing we do know, however, is that they did not part on good terms. In July 2023, Sarah accused Jonah of being an emotionally abusive boyfriend throughout their relationship. She took to her Instagram Stories to post: 

“This is a warning to all girls. If your partner is talking to you like this, make an exit plan. Call me if you need an ear.” 

Jonah Hill is in a relationship with Olivia Miller, the mother of his child 

After being spotted in August 2022, Jonah was linked to the daughter of model, Esmé Marshall, Olivia Miller. According to reports, at the time, the two were seen kissing each other and holding hands while enjoying a date on a beach in Santa Barbara, California. By March 2023, eagle-eyed fans noticed Olivia sporting a diamond ring, sparking engagement rumours with Jonah. Fans were not too far off, as only three months later, a rep for the Superbad star confirmed that the two have been blessed with their first child.  

What are your thoughts on Jonah Hill's extensive dating history? Let us know.  

Also read: Who Is Tylor Chase? Emerged As A Child Actor On Nickelodeon, Currently Living On California Streets

AWESOME NEWS! Now you can download BollywoodShaadis app and never miss a story. Get App

AWESOME NEWS! Now you can download BollywoodShaadis app and never miss a story. Choose your device Android or IOS (Apple)