Keanu Reeves Dating History: Alexandra Grant, Jennifer Syme, More

Legendary actor Keanu Reeves has always lived a very private life — and his relationships were no exception to that rule. His dating history is short and sweet and proves that the Bill and Ted’s Excellent Adventure star doesn’t settle when it comes to romance.

These days, he is dating visual artist Alexandra Grant. In November 2019, Life & Style exclusively broke the news that they were a couple. “Everyone is ecstatic that he’s finally found happiness with such a wonderful woman. Keanu doesn’t stop raving about her! She’s kind, warm and spiritual, just like Keanu, and a great communicator,” a source gushed at the time. “She’s one of the few people who has managed to get Keanu to open up about his emotions and past.”

The pair bonded via their mutual love of art and “spend hours sitting in the garden discussing” it, a second insider gushed to Life & Style in May 2020. “They enjoy painting together and have created so many stunning pieces of artwork.”

The dynamic duo have been joined at the hip since they went public with their romance — but they don’t mind flying solo and tapping into their independence. Keanu and Alexandra “are cool with each doing their own thing,” a third source explained in October 2020. “They’re very much a couple, but completely independent when it comes to doing things on their own.”

In fact, one of the things the Matrix actor loves about the Ohio native is that “she’s completely her own person,” an additional source previously noted before adding that Alexandra is “not needy” as a girlfriend and “doesn’t rely on him to make plans.” Plus, “they travel well together.”

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The insider raved, “Keanu and Alexandra really do have a great relationship.”

Prior to his romance with the painter, he dated actress Jennifer Syme in 1999, and she later gave birth to the pair’s stillborn child, Ava. Shortly thereafter, they split. Jennifer died in a car accident in 2001. “He was in such a dark place for so long, but Alexandra’s positive outlook and support have played a huge part in helping him turn his life around,” a source explained in November 2019. “Some say she’s not only stolen his heart but she’s also saved him.”

Scroll through the gallery below to see Keanu’s full dating history over the years!

Winona Ryder

While the pair didn’t technically “date,” the longtime friends have joked about being married ever since they costarred in 1992’s Bram Stoker’s Dracula. In a 2018 joint interview with Entertainment Weekly for their film Destination Wedding, Winona noted that a “real Romanian priest” presided over their Dracula onscreen nuptials.

“We actually got married in Dracula. No, I swear to God, I think we’re married in real life. We shot the master, and he did the whole thing. So, I think we’re married.” Keanu joked back about the scene in the Francis Ford Coppola film, “Oh my gosh, we’re married.”

The question still lingers though. In a November 2021 video with Esquire, the John Wick star was asked, “Are you and Winona Ryder technically married?” Keanu slyly responded, “We did a whole take of a marriage ceremony with real priests. Winona says we are. Coppola says we are. So, I guess we’re married under the eyes of God.”

Jennifer Syme

“Keanu was so traumatized by her death that there were times when he couldn’t get out of bed in the morning,” an insider previously revealed to Life & Style about Keanu’s ex, with whom he fathered a stillborn child. Jennifer was killed in a car accident in 2001, shortly after they split following their child’s birth.