After years of being a very successful movie star, Keanu Reeves has portrayed several characters that his fans can’t get enough of. More importantly, Reeves has developed a reputation as one of the nicest guys in Hollywood history which makes fans love him even more.

Since Reeves is such a beloved star, fans have a lot of interest in his current girlfriend and whether dating the star has helped her career. What many Reeves fans don’t realize, however, is there is a tragic reason why Reeves seemingly was single for a long time.

Why Was Keanu Reeves Single for So Long?

According to Whos Dated Who, Keanu Reeves became single in the year 2000. That same website reports that Reeves’ next confirmed relationship came in 2005 when he was briefly linked to Diane Keaton.

Via: Instar

Later in 2009, Whos Dated Who reports that Reeves dated Charlize Theron who he was linked to for roughly a year. Finally, Whos Dated Who reports that Reeves began dating his current girlfriend Alexandra Grant in 2018.

Assuming all of Whos Dated Who’s reports are accurate, Reeves has dated a lot fewer people than most celebrities who aren’t married. After all, between the years 2001 and 2023, Reeves only had three relationships that reportedly were confirmed.

From the moment Reeves rose to fame, virtually everyone has agreed he is very attractive. According to Celebrity Net Worth, Reeves has accumulated an impressive $380 million fortune. Reeves also is widely considered to be a genuinely good person.

With everything Reeves has going for him, it seems wild that he has been single for so many years. Tragically, according to reports, it seems to be very likely that there was a very sad reason why Reeves went so many years without anyone by his side.

According to reports including one from People that was published in 2001, it was a huge deal when Reeves became single in the year 2000. On top of that, Reeves had his heart broken a second time the following year.

According to Whos Dated Who, Reeves dated a woman named Jennifer Syme for roughly two years after they became a couple in 1998. During that time, the couple learned they were expecting a baby.

Via: Deposit Photos

Trigger warning: the following paragraph will touch on the tragic subject of pregnancy loss.

In December 1999, Symes and Reeves suffered one of the worst things anyone can go through. Their baby which the couple named Ava was delivered stillborn on Christmas Eve. What many people don’t fully understand is how utterly devastating it is to suffer pregnancy loss of any kind.

According to People’s 2001 report, the former couple’s severe grief came between them and ended their relationship. “The grief proved too much for their relationship, which ended several weeks later.” Still, Reeves and Syme still cared about each other from all accounts and remained close friends.

In April 2001, Syme was driving herself when tragedy struck when she lost her life in a terrible accident that was summarized by People.

“Shortly after 6 a.m. on April 2, Syme, who worked in the recording industry, lost control of her 1999 Jeep Cherokee on L.A.’s Cahuenga Boulevard, sideswiped three parked cars, rolled over several times and was thrown from the car. Authorities believe she died instantly.”

People’s report included some other details that reflected how big of a deal this event was for Reeves. According to People, when Reeves learned that something happened to Syme, he cared about her so much that he began calling to find out where she was.

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“A much shaken Reeves called the Los Angeles County Coroner’s Office and asked, according to Lt. Mac Willie, ‘if Jen Syme was there.'” People also reported that Reeves and Syme had remained so close that they’d gone for brunch the day before her passing.

Finally, People quoted an insider who said that Reeves had a very difficult time coping with Symes losing her life. “[Reeves] is finding it very, very difficult to cope with her death.”

Given the horrible way Reeves’ relationship with Symes played out, it makes sense that he had so few confirmed relationships over the years. That said, there have been many unconfirmed rumors about Reeves dating other notable people over the last two decades.

What Celebrities Has Keanu Reeves Been Rumored To Date?

In the years since Keanu Reeves rose to fame, there have been millions of fans who’ve had crushes on him. Similarly, there have been several celebrities who’ve spoken about being smitten with Reeves.

Most notably, it seems like many of Reeves’ former co-stars have admitted falling for him. A perfect example of that is the viral video of the Ellen DeGeneres interview in which Sandra Bullock spoke about the crush she had on Reeves when they co-starred in Speed.

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Given all the stars who’ve admitted having feelings for Reeves, it makes sense there have been a lot of rumors about him. That said, it is wild to see the list of celebrities that Reeves has been rumored to date at one time or another.

According to Whos Dated Who, some of Reeves’ rumored relationships were with actors, and they took place in the 2000s. During the 2000s, Reeves was rumored to have dated Claire Forlani, Kelli Garner, Lynn Collins, Winona Ryder, Parker Posey, and China Chow among others. In 2009 and 2010, Reeves was also rumored to be involved with Cameron Diaz.

While these rumors are interesting, there are two things to keep in mind about them. First, there may be no truth to any of these rumored relationships. Secondly, according to Whos Dated Who, all of those rumors were short-lived. That means that if Reeves did date any of those women, he very likely wasn’t involved with them for long.