Keanu Reeves is simultaneously notorious for being the nicest guy in Hollywood as he is for remaining tight-lipped about his private life.

So when the 59-year-old actor recently made an extremely rare public appearance with his girlfriend Alexandra Grant, people were quick to pay attention.

Reeves’ most recent confirmed public relationship prior to Grant was with actress Jennifer Syme from 1998 to 2000. The pair briefly reunited in 2001, but an unforeseen tragedy ultimately tore them apart for good.

What happened between Keanu Reeves and Jennifer Syme?

Syme was an American actress and personal assistant who began dating Reeves between 1998 and 1999.

The couple reportedly met at a party in 1998 that was thrown by Reeves’ rock band Dogstar.

At this time, Reeves would have been aged 34, and Syme would have been roughly 26 years old.

Reeves, in 1998, had already seen success with Sandra Bullock from 1994’s Speed, and was about to star in The Matrix.

Syme’s mother Maria St. John, however, later disputed those reports, claiming that they had actually known each other for a decade, and hadn’t met at a party.

St. John also said that she had been with Syme when her daughter had met Reeves, though has never revealed the exact circumstances of their meeting.
Reeves is known for keeping a tight lid on information about his personal life. (Getty)
Reeves and Syme soon announced they were expecting their first child, and according to St. John, tabloids were offering upwards of $US14,000 (approx. $39,000) for a photo of Syme’s bump.

“We’d talked about getting the money and donating it to Caring for Babies With AIDS,” Syme later told Us Weekly, noting that publicity-shy Reeves nixed the idea.

Tragically, Syme and Reeves’ daughter Ava was stillborn at eight months on December 24, 1999.
Jennifer Syme and Reeves reportedly started dating between 1998 and 1999. (Twitter)
Several weeks later, Reeves and Syme had reportedly broken up due to the strain of the loss and grief, but remained close friends.

“Their love wasn’t strong enough to survive the loss of their baby,” a friend told Us Weekly.

By 2001, they had reunited. But by April of that year, everything changed.
Syme and Reeve were quite private. (Twitter)
On the night of April 1, 2001, Syme was at a party at Marilyn Manson’s house. Hours earlier, she and Reeves had eaten brunch together in San Francisco at Crepes on Cole.

She had reportedly been driven home by another guest of Manson’s party, however, shortly before dawn on April 2, Syme left her house.

Syme died aged 28 that morning after losing control of her car and crashing into a row of parked vehicles. Reeves, meanwhile, reportedly called Los Angeles County Coroner’s Office on April 2 asking “if Jen Syme was there”, according to People.

“He was very quiet,” Fred Corral, who claimed to have taken the call, told Us Weekly. “He said he wanted to come to our facility. We told him she’d already been identified and that there was no reason for him to come.”

Reeves, as well as Dave Navarro, Scott Coffey, Anthrax guitarist Scott Ian and director David Lynch were pallbearers at her funeral on April 6 in Los Angeles’ Beverly Hills, which saw her eulogised to Bette Midler’s Wind Beneath My Wings and Barbra Streisand’s Higher Ground.

Reeves reportedly was “visibly upset” throughout the ceremony and reportedly kept his arm tightly around St. John.
Reeves was a pallbearer at Syme’s funeral on April 6, 2001. (GC Images)
Manson, meanwhile, painted her likeness in an artwork titled A Mother Without a Daughter and a Daughter Without a Mother (In Memory of Jen).

Syme was buried next to her daughter at Los Angeles’ Westwood Village Memorial Park Cemetery, and Lynch’s May 2001 film Mulholland Drive was dedicated to her, as seen by a message in the closing credits.

St. John told Us Weekly on April 23, 2001, that Reeves was “not holding up well” following Syme’s shock death.

“She was a very beautiful girl,” St. John said of her daughter, noting how Syme had never recovered from the death of Ava.

“The loss of Ava was the most painful thing that both of them ever had to go through,” she told the outlet.