Keanu Reeves has been in the spotlight for more than three decades and his success has cemented him as one of the best in the business.
The Hollywood star’s movies are among the most successful in modern history, grossing more than £3 billion worldwide and leading him to several Oscar wins along the way.
But away from his glittering career, his love life tells a different story and finding the one certainly hasn’t been straight forward.
READ MORE: Friends’ Matthew Perry says nasty comments about Keanu Reeves will be cut from book
As The Matrix star celebrates his 59th birthday, Daily Star has taken a look at his romantic past, from tragic losses to finding love again with a friend.
Jill Schoelen
(Image: Nbc-Tv/Kobal/REX/Shutterstock)
Keanu met Jill Schoelen on the set of 1986 film Babes in Toyland, starring as married couple Jack and Mary.
They reportedly dated three years after co-starring in the Christmas musical before parting ways.
Immediately after their breakup, the 60-year-old actress moved on with Brad Pitt and the former couple were even engaged for around three months in the 1980s.
Amanda de Cadenet
(Image: WireImage)
Keanu was linked to British socialite and actress Amanda de Cadenet for several months during the 1990s.
But their relationship was far from simple, as Amanda was a teenager and two months pregnant with Duran Duran bassist John Taylor’s child at the time of their meeting.
In her book It’s Messy: On Boys, Boobs, and Badass Women, released in 2018, Amanda opened up about her whirlwind romance with the star and admitted she considered an affair.
She wrote: “We met when I was two months pregnant, 19 years old, and married to another man.
“Within minutes of first laying eyes on him, I remember thinking, ‘I wonder how many pregnant women have affairs?’ I was surprised by my strong attraction to a man I had just met.”
Their short-lived relationship ended as Keanu refused to get involved with a married woman, however, they reportedly dated once her divorce from John Taylor was finalised.
Jennifer Syme
(Image: Mission Pictures)
It appeared things were falling into place when Keanu met actress Jennifer Syme in 1998 and their romance flourished.
In 1998, Jennifer fell pregnant with the couple’s first child.
But eight months into her pregnancy, she gave birth to a stillborn daughter named Ava.
It was believed the overwhelming loss put a strain on their relationship and the couple eventually broke up.
(Image: EMPICS Entertainment)
They remained good friends and were allegedly on the verge of reconciling when disaster struck once again.
On her way to a party at Marilyn Manson’s house in 2001, then 28-year-old Jennifer was killed instantly in a car crash.
Keanu was one of Jennifer’s pallbearers at her funeral and she was laid to rest beside their daughter.
In 2006, he opened up about the agonising depths of his pain, telling Parade magazine: “Grief changes shape, but it never ends.
(Image: UGC)
“People have a misconception that you can deal with it and say, ‘It’s gone, and I’m better’. They’re wrong. When the people you love are gone, you’re alone.”
“I miss being a part of their lives and them being part of mine. I wonder what the present would be like if they were here – what we might have done together. I miss all the great things that will never be.”
Alexandra Grant
(Image: Getty Images for LACMA)
Keanu found love again in 2019 when he began dating artist Alexandra Grant, 50, and the couple have always remained fiercely private about their romance.
They made their red carpet debut walking hand-in-hand at the LACMA Art + Film Gala that same year.
Despite their relationship beginning in 2019, it is believed the couple first met in 2009 and became close friends after working together on a series of projects.
(Image: WireImage)
Alexandra has illustrated two of Keanu’s books – Ode To Happiness in 2011 and Shadows in 2016 and the couple also co-own X Artists Books, founded in 2017.
The John Wick star gave a rare insight into their romance when revealed his “last moment of bliss” came with his partner.
“A couple of days ago with my honey,” he told PEOPLE earlier this year. “We were in bed. We were connected. We were smiling and laughing and giggling. Feeling great. It was just really nice to be together.”
Sandra Bullock crush
(Image: 20th Century Fox)
Back in 2019, Keanu admitted to having a crush on his Speed co-star Sandra Bullock.
The Canadian actor made the confession during an appearance on The Ellen DeGeneres Show, revealing he didn’t make a move because he wanted to keep things professional.
It came after Sandra, 59, admitted she had a crush on Keanu during the filming of the 1994 action flick just one year prior.
(Image: Peter Brooker/REX/Shutterstock)
“Did you know that she had a crush on you?” the comedian asked after playing the clip of Sandra’s confession.
He replied: “No. She obviously didn’t know that I had a crush on her, either.”
As the audience cheered, the 65-year-old quipped: “I can’t believe you both had crushes on each other… and you were so scared.”
“We were working!,” he replied, before hinting he did once have a workplace romance.
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Source: Celebrities - dailystar.co.uk
