Jonah Hill’s dating timeline: All his relationships in order

Jonah Hill is attracting heightened attention as of late and for all the wrong reasons. Former girlfriend Sarah Brady recently accused the star of emotionally manipulating her throughout their relationship, leading to the 22 Jump Street star being placed under the category of one of Hollywood’s most potentially toxic ex-boyfriends.

No doubt as a result of the criticisms, the shocking piece of information has piqued interest in Hill’s dating life in detail. Here’s the list of women Hill has dated in the past.

Jordan Klein

Both Hill and Klein met at Crossroads High School in Santa Monica and a few years later in 2011 publicly announced their relationship, coincidentally not long before the pair would break up.

The cause of the split is unknown, but a source closer to the pair reached out to Us Weekly and explained that the major reason could be professional incompatibility.

“Jordan always seemed really happy and in love. I never heard a single complaint about their relationship. It was probably traveling. She would always go where he was. Now that she has a stable job, she can’t just pick up and leave.”

Ali Hoffman

A few months following his breakup with Klein, Hill began dating Justin Hoffman’s daughter, Ali Hoffman. The relationship lasted for nine months.

Not much light has been shed on the pair’s dating life, except that they met each other through a mutual friend as per the details shared by Us Weekly and that their romance was a major inspiration for James Franco’s 2016 comedy movie, Why Not?

Rita Ora

After his breakup with Hoffman, the War Dogs actor was linked with English singer Rita Ora, who at the time was dating Rob Kardashian. Apparently, she cheated on him with Hill, causing enormous scandals as well as making her the subject of Rob’s wrath, who bombarded her with angry tweets.

Not much is known about their relationship except that it was likely fleeting. As per a source, the “Hot Right Now” singer spent the night with the actor on her trip to New York which was later discovered by Rob.

Isabelle McNally

In September 2013, Hill was seen being photographed together with actress Isabelle McNally. Four months later in January 2014, they made their relationship public. However, a source closer to the duo reached out to Us Weekly claiming that both Hill and McNally began their dating journey way before that.

The date of their breakup is unclear, but it can be said that it must have lasted only a few months as come May, he was linked with Brooke Glazer.

Brooke Glazer

Hill began dating LA-based nutritionist, Brooke Glazer in 2014, with their relationship believed to have lasted for a significant portion of that year. The exact date of their split is unknown, but it is believed that it must have been around early 2015 or late 2014.

Gianna Santos

After a hiatus of three years, Hill once again made his way into the dating market and this time it was a committed relationship with photographer and content manager Gianna Santos. Despite keeping a low profile, their relationship received public attention after the couple got engaged. Unfortunately, it didn’t last long, as the couple called it quits in 2019.

Sarah Brady

Perhaps Hill’s most publicized romance was with surf instructor Sarah Brady, who he dated for around a year from 2021 to 2022. It wouldn’t be until July 7 the following year that Brady would provide details of their relationship, accusing Hill of being ‘emotionally abusive.’ On her Instagram Story, Brady shared a series of conversations between her and the actor where the latter seemed to have set boundaries and rules for Brady to follow.

The rules demanded Brady stop mingling with male friends, give up on modeling as a potential career, take down surfing videos from social media, and quite a few others. The 26-year-old surfer added how complying with them heightened her anxiety and challenged her mental health.

“I too struggle with mental health but I do not use it to control [people] like he did to me,” is what she wrote in one of her Instagram stories indicating the passive position she was being subjected to. Hill has yet to comment.

Olivia Millar

In August 2022, Hill entered into what’s deemed his most serious relationship with the owner of vintage store Chasseresse. Even though they kept their relationship out of the public radar, speculations about their engagement started circulating when Millar was spotted wearing a diamond ring. In March 2023, she was also seen with a baby bump suggesting that the couple are expecting their first child.