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Where were you when you first heard the Barack Obama and Jennifer Aniston affair rumors?! In August 2024, In Touch Weekly published a story in their magazine with the words “The Truth About Jen & Barack!” emblazoned on the cover in all caps. In the confines of the print magazine, the outlet reported that writer, editor, and podcast host Lindsey Weber claimed on an episode of her podcast “Who? Weekly” to have heard from “reliable sources” that Barack and his wife Michelle Obama were living separately and that Barack and Aniston were engaging in a sexual affair. While Weber was careful to follow up the allegation by acknowledging the whole thing could’ve been completely fabricated, In Touch took the gossip and ran with it, and that’s how the Barack and Aniston affair rumors really got started!
As one can imagine, it wasn’t long before everyone was weighing in on the purported dalliance. Things got so bad that in October 2024, Aniston attempted to clear up the rumor once and for all during an appearance on “Jimmy Kimmel Live!” Ironically, however, her response to the Barack affair rumors isn’t what we expected. While she vehemently denied that anything inappropriate had ever gone on between her and the former president of the United States, she did joke that she “was not mad at” the wild rumor. She also went on to say that she had met Barack once but knew Michelle better.
Unfortunately, this isn’t the first time Barack has been accused of being unfaithful. In 2017, one of Barack’s former girlfriends came forward, claiming that he had been guilty of committing some ex-recycling and serious overlapping transgressions. Let’s take a walk down Barack’s memory lane, shall we?
Sheila Miyoshi Jager claims that Barack Obama juggled her and Michelle Obama at the same time
Buckle up because it’s time for a blast from the past! In 2017, long before those pesky affair rumors started circulating about Barack Obama and Jennifer Aniston, a woman from the former president’s past came crawling out of the woodwork. Enter: Sheila Miyoshi Jager, one of Barack’s ex-girlfriends from the 1980s. During a no-holds-barred interview with David Garrow for his book “Rising Star: The Making of Barack Obama” (via People), Jager claimed that the pair rekindled their love affair from 1990 to 1991. The only problem? Barack was also dating his now wife and future first lady, Michelle Obama. “I always felt bad about it,” Jager told Garrow about her sordid love affair with Barack.
In the confines of his book, Garrow revealed the intricate details of the relationship as recounted to him by Jager. The story goes that Jager and Barack dated for three years in the mid-1980s, even cohabiting at one point. The kicker? Garrow wrote that Barack also proposed to Jager not once, but twice. Jager, however, maintains that she declined both of the future president’s proposals with a “not yet” on account of her parents telling her she was too young to get married. At the time, she was 23 and Barack was 25.
By 1987, however, the couple quietly went their separate ways, with Jager relocating to South Korea. During that time, Barack met Michelle while working at a Chicago law firm, and for all intents and purposes, it seemed that the couple were well on their way to a life of matrimony together. Alas, as the old saying goes, old habits die hard. According to Jager, that’s exactly what happened when Jager and Barack both found themselves at Harvard together in January 1990, with him studying at the law school and her there on a teaching fellowship. “We continued to see each other occasionally despite the deepening of Barack’s relationship with Michelle,” Jager revealed to Garrow. By the spring of 1991, however, Jager had found someone else, too. The following summer, Barack proposed to Michelle, and the rest is simply history. “As much as I loved him, I was relieved when our paths finally parted,” Jager confessed. All’s well that ends well, we suppose.
