Yep, Jennifer Aniston once had her heart set on The Matrix star himself, Keanu Reeves. And while her crush didn’t exactly pan out, that unrequited spark left a bit of Hollywood awkwardness that lingered long after. Sandra Bullock caught herself between her two close friends and walked a delicate line in the following years.
Aniston’s crush on Reeves returned for a while, with sources telling In Touch that her feelings for him grew especially strong after 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 breakup,” shared the insider. Unfortunately, Reeves didn’t seem interested, which reportedly left Aniston a little embarrassed, with some of that tension quietly hanging in the background ever since.
For Sandra Bullock, the whole situation was a balancing act. She and Reeves had developed a close friendship during their “electric” connection on Speed, and they’d stayed good friends ever since. “We liked hanging out,” Reeves recalled in a recent chat on the 50 MPH podcast, adding, “We just liked each other.” Bullock felt it, too. “It was so electric,” she said. “I felt very comfortable with Keanu.” They’d acknowledged a chemistry, but the timing was never quite right. Years later, Reeves found happiness with artist Alexandra Grant, whom he’d been dating since 2019, and Bullock couldn’t have been happier for him.
However, Aniston’s old crush added a subtle tension, especially as Bullock navigated her friendships with both stars. Aniston had never really shaken her embarrassment over Reeves’ lack of interest, and Bullock, always loyal, tried her best to respect that. “Sandy is so loyal to her friends, and Jen has been such a huge support to her this year,” the source revealed. “She would never want to do anything to make her uncomfortable.”
In a perfect world, Bullock would’ve been hosting cozy dinners with Aniston, Reeves, and Grant around the same table, sharing laughs, and maybe even planning group trips. “She loves Keanu and thinks Alexandra is fantastic,” the source added. But Aniston’s history with Reeves made it challenging to bring her friends together fully. Bullock didn’t let it stop her; she stayed close to both, always finding ways to keep things smooth without reopening any old wounds.
So, while Bullock may have had to tiptoe around the friendship dynamics, she remained a pro at keeping her relationships strong and drama-free. And while it might not have been the most comfortable situation, her dedication to her friendships with Aniston and Reeves showed how deeply she valued them.
Who knows? Maybe one day, Bullock’s dream dinner party will finally happen, with everyone laughing over old memories and lingering crushes.
For more such updates, check out Hollywood News.
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