Bradley Cooper is one of Hollywood's most in-demand leading men—on and off camera.

While Cooper, who turned 49 on Jan. 5, has always remained notoriously private about his personal life, it hasn't stopped the public from being interested in his relationships. That might just be because the filmmaker has had several high-profile romances since his breakout performance in 2009's The Hangover, including courtships with former co-stars like Zoe Saldana and Renee Zellweger.

Most recently, Cooper has sparked romance rumors with Gigi Hadid, as the actor and model have been spotted multiple times together in New York City, including a star-studded dinner with the likes of Taylor Swift and Selena Gomez. Plus, Hadid showed her support for Cooper when she popped up at his Danny & Coop's Cheesesteak food truck last month. 

But the most important woman in the A Star Is Born director's life is Lea, his 6-year-old daughter with ex-girlfriend Irina Shayk and the inspiration behind his production company, Lea Pictures.

And while supermodel Shayk didn't join the pair when Lea made her red carpet debut at the Dec. 12 premiere of his new film Maestro, she did give Cooper—whom she date for four years before their breakup in 2019—a shout-out on social media. "Congrats @maestrofilm," Shayk wrote on her Instagram Stories. "So proud Daddy and Lea."

But Shayk isn't the only ex-girlfriend Cooper has stayed friendly with after a breakup. Look back on the nine-time Oscar nominee's surprising dating history, including a Daisy Jones and the Six star and his four-month marriage to Jennifer Esposito.

We bet you didn't know that Bradley Cooper was married. For four months. To actress Jennifer Esposito. 

After making their first red carpet appearance as a couple at the 2006 Golden Globes, Cooper and Esposito were engaged by October and got married on Dec. 21, 2006, in the south of France.

But their wedded bliss was short-lived as Esposito filed for divorce on May 1, 2007, citing irreconcilable differences.

At the time, a rep for Cooper called the split "mutual" and noted that they had been "separated for quite a while," despite only being married four months total, their divorce being finalized in November 2007.

The notoriously private actor and director briefly discussed his marriage on The Howard Stern Show in 2011, saying, "It was just something that happened,"

"The good thing is, we both realized it...Sometimes you just realize it," he continued. Howard Stern, of course, wanted to know much more, but Cooper insisted, "It just wasn't right. It's interesting...things happen!"

After meeting on the set of their film Case 39, which was filmed in the summer of 2009, The Hangover star and Zellweger garnered a lot of attention for their romance, despite both stars never speaking publicly about their relationship. The pair did, however, gush about one another professionally.

"I can't say enough about her. I just love her. I [loved] coming to work," he told Entertainment Tonight in 2010. "I love acting with her. I can learn so much from her."

Zellweger returned the compliment, calling Cooper "a great, great actor." She added, "I just got so excited, not believing that I was going to go to work with him."

They dated for two years before breaking up in March 2011, just as Cooper was completing filming on the movie Limitless.

But there seems to be no hard feeling between the exes as they enjoyed a reunion at the 2020 Oscars, where Zellweger won the Best Actress award for her role in Judy. 

Years before they co-starred as team members in Marvel's Guardians of the Galaxy franchise, Cooper and Saldana quietly dated.

"Bradley is a very dedicated and open professional," Saldana told The Hollywood Reporter at the time of her co-star in 2012's The Words. "It’s really good when you can balance that with an actor as opposed to an actor that just comes prepared and just goes, 'Don’t f--k up my light' and 'this line is my close-up.'"

As for their chemistry while filming? "We didn’t care where was the camera was," she shared. "It was just like we were both part of this extensive conversation.”

Their year-long relationship fizzled out in late 2012, with a source telling E! News at the time that their busy schedules lead to their split. 

 "They both have a lot going on right now," the source said. "She has a bunch of movies coming out this year, so it was really important for her to be spending time with her family."

First linked to Cooper in 2013, Waterhouse had no interest in divulging details on her relationship with the Oscar nomine.

 "I don't talk about my boyfriend because it's boring," she told Elle U.K. at the time. "At least, that's what I decided to tell you when you asked. I do think whatever I say will sound weird. But the truth is, if I start talking about him, I probably won't be able to stop. And I don't really want to talk about him, you know?"

The pair would go on to make several red carpet appearances together before E! News exclusively confirmed their split in March 2015. At the time, a source noted that they "remain friends but they both want different things."

While Waterhouse or Cooper have never publicly commented on their two-year relationship, fans believe she may have called out her ex last January with the release of her single "Melrose Meltdown."

In a since-deleted TikTok, the Daisy Jones and the Six star, who is expecting her first child with Robert Pattinson, posted a snippet of the song and used a filter that gave the appearance of a lightly colored beard, captioning the clip "Can't believe I let someone who looks like me with this filter break my heart."

When a user commented on her video, "Bradley Cooper besties," Waterhouse hit the thumbs-up button.

Cooper began dating Shayk in April 2015 and the pair were first publicly spotted together when they attended a Broadway show. Shortly thereafter, a source told E! News that things were quickly "heating up" between the pair. 

By the spring of 2016, the pair took two major steps in their relationship—walking their first red carpet as a couple and making their romance Instagram official. And the following year, Cooper and Shayk welcomed their first child together, daughter Lea de Seine Shayk Cooper. 

But in 2019, Cooper and Shayk were the subject of breakup reports amid rumors about the chemistry between Cooper and his A Star Is Born co-star, Lady Gaga.

While there was no truth to the speculation about Cooper and Gaga's romance, he and Shayk ended their four-year relationship in June 2019.

After their split, however, Cooper and Shayk have remained friendly, even going on vacation together last summer, with Shayk sharing an image of the Silver Linings Playbook star relaxing in a kayak to her Instagram Story. 

The model opened up about their co-parenting relationship in November, explaining that even though she and the Oscar nominee have equally busy schedules, they put 6-year-old Lea first.

"We always find a way," Shayk told Elle, adding that Cooper is "the best father Lea and I could dream of. It always works, but it always works because we make it work."

Cooper was briefly linked to Hilary Clinton's longtime aide—who was previously married to disgraced congressman Anthony Weiner—in the summer of 2022 after they were reportedly set up by Vogue editor-in-chief Anna Wintour. 

It was unclear exactly when their romance began, though Cooper and Abedin were both in attendance at the 2022 Met Gala in May. However, they were photographed separately on the red carpet at the star-studded fashion event, which is co-chaired by Wintour.

Cooper and Abedin never publicly addressed their rumored relationship.

One of the most surprising celeb couples of 2023? Cooper and Hadid, with the pair first sparking romance rumors when they were spotted together in October.

The Maestro star and supermodel—who co-parents 3-year-old daughter Khai Hadid Malik with ex-boyfriend Zayn Malik—have been photographed together in New York multiple times, including a group dinner with Hadid's friends Taylor Swift, Selena Gomez, Sophie Turner, Cara Delevigne and Brittany Mahomes.

And Hadid publicly supported Cooper when she stopped by the actor's Danny & Coop's Cheesesteak food truck to see him sling sandwiches to New Yorkers on Dec. 6. (Cooper's ex Shayk also made a separate appearance.)

Sporting a cozy-looking black sweat set underneath a shearling-lined denim jacket, an eyewitness told E! News that the 28-year-old arrived with actress Laura Dern and picked up her order to-go from her rumored boyfriend.