The Surprising Love Life of Jonah Hill: Unveiling His Iconic Relationships and Romantic Escapades!

Jonah Hill, despite maintaining a low profile in his personal life, has been connected to multiple women, regardless of whether the interactions were brief or long-lasting.

In an interview with Seventeen magazine in June 2010, he confessed, "I've had to patiently wait for relationships to end before pursuing someone I'm interested in. If you genuinely love the person, believe you're meant to be together, and it feels right, waiting it out is worth it."

Hill was previously involved with Jordan Klein, his high school acquaintance. They maintained a relationship for three years before parting ways. After their separation, Hill engaged in romantic associations with individuals such as Rita Ora, Alana Haim, and his former fiancée Gianna Santos. Subsequently, in October 2021, he confirmed his involvement with surfer Sarah Brady through an Instagram announcement.

Hill and Brady made their first public appearance as a couple on the red carpet at the premiere of Don’t Look Up in December 2021. Two months later, he addressed and dismissed engagement rumors through a now-deleted Instagram post. He humorously stated, "Yes, I'm engaged, but not to my girlfriend. I am engaged to your mom. I understand that this may come as a shock, but we kindly request privacy at this moment."

The exact timeline of the couple's breakup remains unknown, however, Hill was first seen with his girlfriend Olivia Millar in August 2022.

Hill has expressed his primary objective in life as finding contentment and fulfillment, irrespective of his romantic situation.

"When questioned about my occupation, I find that work effortlessly comes to me," shared the actor from "22 Jump Street" in an interview with GQ Style in August 2021. "What I truly desire is happiness. My mission in life is to attain genuine happiness, and I am dedicated to working diligently towards that."

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

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

Jonah Hill has always maintained a level of privacy regarding his personal life, but he has been connected to various women, whether it was a short-lived romance or a more serious commitment. In a June 2010 interview with Seventeen magazine, he admitted to sometimes waiting for others to end their relationships before pursuing someone he is interested in. According to Hill, if it feels like the right person and he truly loves them, he is willing to be patient and wait for the right timing.

Hill was previously in a relationship with Jordan Klein, whom he had known since high school. They were together for three years before breaking up. After their split, Hill had romantic relationships with Rita Ora, Alana Haim, and his former fiancée Gianna Santos. In October 2021, he confirmed his relationship with surfer Sarah Brady through an Instagram post.

Hill and Brady publicly appeared together for the first time on the red carpet at the premiere of Don't Look Up in December 2021. However, just two months later, he took to Instagram to dismiss rumors of their engagement in a now-deleted post. In a playful manner, he confirmed, "The rumors are true - I am engaged. But not to my girlfriend. I am engaged to your mom. I understand this may come as a surprise, so I kindly request that you respect our need for privacy during this time."

Although the exact breakup timeline remains undisclosed, Hill was seen with his girlfriend Olivia Millar for the first time in August 2022.

Hill has stated before that his ultimate aim in life is to achieve happiness and fulfillment, regardless of his romantic situation. He expressed this sentiment in an interview with GQ Style in August 2021, saying that work is something that comes easily to him and that his main focus is on his personal happiness.

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

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Jordan Klein

The actor from 21 Jump Street and Klein were in a relationship for three years before calling it quits, as confirmed by We in October 2011. According to a source, Klein always appeared to be very happy and deeply in love with her, before their breakup. The insider speculated that the reason for their split was likely due to the challenges of traveling. Klein used to accompany him wherever he went, but now that she has a steady job, it becomes difficult for her to just up and leave.

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Ali Hoffman

Hill dated the daughter of actor Dustin Hoffman for a span of nine months before their split was confirmed by Us in September 2012. The Superbad star had been acquainted with Ali’s family for quite some time, as it was reported that they had both attended the same high school.

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Rita Ora

The British songstress,

Rita Ora

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Alana Haim

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

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Isabelle McNally

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.

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Brooke Glazer

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.

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Gianna Santos

After being in a relationship for almost a year, Hill asked the Violet Grey content manager to marry him in September 2019. Nevertheless, the couple decided to go their separate ways in October 2020. An exclusive source informed Us at that time, "The connection between Jonah and Gianna faded away in their relationship."

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Sarah Brady

Hill confirmed his romance with Brady in September 2021, posting a selfie of the pair via Instagram. He captioned the snap, “️ grateful for you @sarahhbrady.”

Brady, on her end, posted multiple pictures with her boyfriend on social media, including a selfie of them kissing in August, captioned "He means the world to me." However, they eventually ended their relationship, although the specific timing of their breakup is unclear.

In July 2023, Brady publicly accused her former partner of emotional abuse during their time together. She warned other girls about such behavior and encouraged them to create a plan to leave the relationship. She also offered her support, stating, "Feel free to reach out if you need someone to listen."

Brady shared text messages from Hill where he asked her to remove her surfing pictures from Instagram that showed her wearing a thong. Despite complying with his request, Hill claimed in the screenshots that Brady still didn't understand his point.

Hill allegedly wrote in a text that it was not his responsibility to teach Brady. He stated that he had clearly set his boundaries, and no longer wanted her to surf or have inappropriate friendships with men, post bathing suit pictures, or maintain friendships with women from her past beyond casual lunches or coffees. Hill concluded by saying that Brady's refusal to let go of certain friendships was apparent, and he hoped it brought her happiness.

Brady also shared with her fans that she is currently in the process of healing following her separation from Hill. She mentioned that during their time in therapy, she took responsibility for his actions, but now recognizes that his behavior was not acceptable. She concluded her message by clarifying that Hill is not a "terrible person," but his actions were not "OK."

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Olivia Millar

In August 2022, Hill was seen with the owner of a vintage shop, engaging in displays of affection such as kissing and holding hands during a beach trip in Santa Barbara, California. In March 2023, speculation about their engagement arose after Millar was photographed wearing a diamond ring. Confirming the rumors, a representative for the Superbad actor revealed three months later that the couple had discreetly become parents to their first child.