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Reading: Jennifer Aniston Isn’t Alone—All the Women Barack Obama Is Rumored to Have Dated
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Politics

Jennifer Aniston Isn’t Alone—All the Women Barack Obama Is Rumored to Have Dated

Published on: July 26, 2025 at 6:04 AM ET

Barack Obama's infamous affair rumor with actress Jennifer Aniston is the only one; allegedly, there are more

Sweta Choudhury
Written By Sweta Choudhury
News Writer
Mohar Battacharjee
Edited By Mohar Battacharjee
Senior Editor
Barack Obama and Jennifer Aniston ( left-@TheCalvinCooli1|X) and ( right-@Dida_movies|X).
Barack Obama and Jennifer Aniston ( left-@TheCalvinCooli1|X) and ( right-@Dida_movies|X).

Former President Barack Obama served in the White House as the 44th president from  2009 to 2017. The first African American President left office with high approval ratings both within the United States and among foreign leaders. He continues to reside in Washington, D.C. He is political active as he provides support to essential campaigns and stands up for causes that matter to him.

In his personal life, Barack Obama is married to former First Lady, entrepreneur, and philanthropist Michelle Obama. They married on October 3, 1992, and share two daughters.

Usually, the couple is considered one of the ideal pairs who have dealt with all the ups and downs life has to offer. Public scrutiny, busy life in the White House during Obama’s tenure, and alleged divorce rumors, which ranked in the tabloids for quite some time.

Barack and Michelle Obama with Malia and Sasha
Barack and Michelle Obama with Malia and Sasha. (Image source: Twitter)

As per Nicki Swift, several people said the divorced stemmed from the distance between the couple after Michelle Obama did not attend Donald Trump‘s inaugural ceremony and Jimmy Carter’s funeral. Still, many others also claimed the former president had an affair. Buzz of an affair between Barack Obama and Jennifer Aniston caused quite a stir in August 2024 when In Touch Weekly featured a bold headline: “The Truth About Jen & Barack!”

The magazine cited claims made by podcast host Lindsey Weber on an episode of Who? Weekly, she shared hearsay from “reliable sources” suggesting Barack and Michelle Obama were living apart. Though Weber herself admitted the rumor might be entirely made up, the tabloid ran with it, and the gossip quickly gained a lot of public attention.

As the speculation spread, Jennifer Aniston finally addressed it during an appearance on Jimmy Kimmel Live! in October 2024. She firmly denied any romantic involvement with Mr Obama.  “That is absolutely untrue,” she said. Further, she added that she wasn’t offended by the speculation, after all, all celebrities are used to gossip like this from time to time.

Friends star Jennifer Aniston also claimed that she only met President Obama once and knew his wife Michelle better. Furthermore, there was another woman Obama was linked with apart from Aniston. Reportedly affluent political figure maintained a relationship with Sheila Miyoshi Jager, and the two were quite in love.

Talking of Barack Obama, Jager spoke openly about her past with Barack. The two dated throughout the mid-1980s and even lived together for a time. Jager claimed that Obama proposed to her twice, but she turned him down due to her parents’ concerns that she was too young to marry (she was 23; he was 25).

Michelle Obama–Angry Black Woman. Bitch.

Poor Obama.

He had white girlfriends before having to “Black himself up” with that horrible Michelle.

There was Genevieve Cook.

He even proposed to another, Sheila Miyoshi Jager.

His lover letters to Alexandra McNear were also… https://t.co/C00xwVRjeK pic.twitter.com/oHeIQYyv3m

— An Observer (@walsh_coman) January 14, 2025

They eventually split in 1987, and Jager moved to South Korea. Meanwhile, Obama began dating Michelle while working at a law firm in Chicago. However, according to Jager, the two briefly reconnected in 1990 when both were at Harvard—Barack as a law student, and Jager on a teaching fellowship. Despite Barack’s growing relationship with Michelle, Jager said they continued to see each other occasionally until she entered a new relationship in 1991.

Jager reflected on the situation with mixed emotions: “As much as I loved him, I was relieved when our paths finally separate ways. Barack Obama never publicly addressed Jager’s claims but mentioned their relationship in his memoir “Dreams From My Father” without naming her, describing it as established on mutual interest.

Obama and Michelle married on October 3, 1992. After suffering a miscarriage, Michelle underwent in vitro fertilisation to conceive their daughters Malia Ann (born 1998) and Natasha (known as Sasha, born 2001). The Obama family lived on Chicago’s South Side, where Barack taught… pic.twitter.com/YSPIteGiLf

— AlphaBravoCharlie (@alphabravo1947) January 3, 2024

This gossip did not come out then, as the woman wasn’t a publicly famous one, nor was Obama who he is today. “Very sweet lady, as busy as I am and so temperamentally well-suited,” he wrote about her in the memoir, which talks a lot about his personal life that goes beyond his political image.

Did you know that before Barack Obama met Michelle Obama, that he had a long-time relationship with a white woman who he was engaged to marry? That woman is leftist historian Sheila Miyoshi Jager. Why has the news media been hiding this? pic.twitter.com/kwgntKEumV

— The Political Bandit (@politclbandit) August 6, 2023

As they say, the past is history and the future is a mystery; all we have is today, which is a gift. Hence, we hope Barack and Michelle are happy in their world, nurturing their beautiful family and living their lives with dignity and love. 

TAGGED:Barack ObamadonaldJennifer AnistonMichelle ObamaWhite House
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