Despite Keanu Reeves’ current relationship with Alexandra Grant, his past with Jennifer Aniston continues to cast a shadow over their interactions.
Jennifer Aniston’s old crush on Keanu Reeves has created an ongoing, delicate tension. A source told In Touch that this lingering issue has put Sandra Bullock, a mutual friend of both stars, in an awkward position as she navigates her relationships with them.
According to the source, Aniston, now 55, had a significant crush on Reeves years ago, but her advances were not reciprocated, leaving behind a lingering tension. This has been particularly challenging for Bullock, 60, who has had a close friendship with Reeves, 59, since their time working together on the set of Speed in 1994.
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The source shared, “Sandra and Keanu are getting along great, and she’s happy to see him so in love with Alexandra [Grant].” Reeves has been in a committed relationship with artist Alexandra Grant, 51, since 2019. However, the strong bond between Bullock and Reeves has made the situation awkward, especially considering Aniston’s past feelings.
In a recent interview on the “50 MPH” podcast, Reeves reflected on his chemistry with Bullock during Speed, describing their relationship as occasionally flirty. “We liked hanging out. We just liked each other,” Reeves said, with Bullock adding, “It was so electric. I felt very comfortable with Keanu. You just go, ‘OK, there’s my partner.’”
Although there was a mutual attraction, both Reeves and Bullock have acknowledged that the timing for a romance between them was never right. With Reeves now devoted to Grant, Bullock continues to value her friendship with him, even as Aniston’s past crush adds complexity to their social dynamics.
The source revealed that Aniston’s feelings for Reeves were particularly intense after her breakup with Brad Pitt. “Jennifer was very forward with him after her split with Brad, trying to assert herself,” the insider noted. “She still feels awkward about how things went down, and this situation has lingered ever since.”
Caught in the middle, Bullock remains close to both Aniston and Reeves but finds herself navigating the tension carefully. “She adores Keanu and thinks Alexandra is wonderful, so ideally, she’d love to have them all together for dinners or trips,” the source said.
However, the awkwardness stemming from Aniston’s past has made it challenging for Bullock to socialize with both as freely as she would like. “Sandra is fiercely loyal to her friends, and Jennifer has been a major support this year. She wouldn’t want to make anyone uncomfortable, but Jen does feel a bit embarrassed about the situation with Keanu,” the source added.
