A real rom-com: Jimmy Kimmel is desperately trying to set up Jennifer Aniston with Bill Hader
HOLLYWOOD, CALIFORNIA: Jimmy Kimmel is playing cupid as he wants his friends, Jennifer Aniston and Bill Hader, to become a couple. According to sources, the late-night host is desperate to find love for the two, who have both stayed unlucky in relationships after their respective divorces from Meggie Carey and Justin Theroux.
The 44-year-old 'Barry' actor has dated several Hollywood actresses, including Rachel Bilson, Anna Kendrick and Ali Wong. On this backdrop, sources reportedly said, "His love life has been messy and inconsistent." Aniston, 53, recently shared her struggles with IVF and said she was now "ready to share myself with someone." "It would give Jen a window into the kind of family life she's always wanted but basically gave up on years ago. Jimmy would love to see them together," and insider told RadarOnline.
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Aniston has only married twice. Her first husband was Brad Pitt. America's loveliest couple called it quits in March 2005. Although Aniston listed irreconcilable differences in her divorce petition, all indications pointed to Pitt and his 'Mr & Mrs Smith' co-star Angelina Jolie's on-screen connection as the cause of the split.
Jolie and Pitt had six children together before she filed for divorce in 2016 and now, the two are embroiled in a bitter divorce battle and are fighting for custody of their children. They were also involved in a dispute over the vineyard they formerly owned together as a result of her selling the company shares behind Pitt's back.
Despite all of the drama, Aniston and Pitt were spotted together for a live table reading of 'Fast Times' at Ridgemont High. Speaking on SiriusXM's 'The Howard Stern Show' in 2021, Aniston made it clear that there was no awkwardness between them. "It was absolutely fun. Brad and I are buddies, we're friends. We speak, and there's no oddness at all, except for everyone that probably watched it and was wanting there to be, or assumed there to be. We had fun, and it was for a great cause," she reportedly said.
Pitt and Aniston were married from 2000 to 2005. She appeared with him on an episode of Friends from 2001. It is believed the exes have since rekindled their friendship, with Pitt attending her 50th birthday in 2019.