Jennifer Aniston's past crush on Keanu Reeves creates awkward tensions with Sandra Bullock

Despite Keanu's current relationship with Alexandra Grant, the past still casts a shadow over their interactions.

Jennifer Aniston’s longstanding crush on Keanu Reeves has created a delicate and awkward dynamic that continues to linger, even years later. According to a source exclusively speaking to In Touch, the situation has put their mutual friend, Sandra Bullock, in an uncomfortable position as she navigates her close relationships with both stars.

The source reveals that Aniston, 55, developed a major crush on Reeves back in the day, but her advances were met with a cold shoulder, which has led to lingering tension ever since. This is especially tricky for Bullock, 60, who has maintained a deep friendship with Reeves, 59, since they first met on the set of Speed in 1994.

“Sandy and Keanu are getting on so well right now, and she’s thrilled to see him so madly in love with Alexandra [Grant],” the source shared. Reeves has been in a committed relationship with artist Alexandra Grant, 51, since 2019. However, the close bond between Bullock and Reeves has led to some awkwardness, particularly given Aniston’s past feelings.

In a recent interview on the “50 MPH” podcast, Reeves reflected on his connection with Bullock during the filming of Speed, describing their relationship as sometimes flirty. “We liked hanging out. We just liked each other,” Reeves said, to which Bullock added, “It was so electric. I felt very comfortable with Keanu. You just go, ‘OK, there’s my partner.’”

Despite rumors and a strong mutual attraction, both Reeves and Bullock have previously admitted that the timing for a romance between them was never quite right. Now, with Reeves committed to Grant, Bullock continues to cherish her friendship with the actor, even as Aniston’s past crush adds complexity to their social interactions.

The source disclosed that Aniston’s feelings for Reeves were particularly intense following her breakup with Brad Pitt. “Everyone knows [Jennifer] threw herself at him years ago when she was single and trying to prove herself after the break-up with Brad,” the insider revealed. “She’s still embarrassed by the way she acted, and it’s one of those awkward situations that has lingered ever since.”

Bullock, who values her friendships deeply, is now caught in the middle of this tension. She remains close to both Aniston and Reeves, yet finds herself having to tiptoe around the situation to avoid making anyone uncomfortable. “She loves Keanu and thinks Alexandra is fantastic, so in a perfect world, she’d have them all over to the house for dinners and maybe even do trips away together,” the source said.

Unfortunately, the awkwardness between Aniston and Reeves has made it difficult for Bullock to socialize with them as freely as she would like. “Sandy is so loyal to her friends, and Jen has been such a huge support to her this year. She would never want to do anything to make her uncomfortable, and unfortunately, Jen does feel a little foolish about the situation with Keanu,” the source added.