‎Inside the Story of Barack Obama's College Love — the Woman He Proposed to Twice Before Michelle ‎

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Inside the Story of Barack Obama's College Love — the Woman He Proposed to Twice Before Michelle
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‎Before Barack Obama became a global icon and US president, he shared a deep, formative relationship with a woman who didn't become his wife. An old biography uncovered the little-known story of the woman he asked to marry him, twice.
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‎While many people view former US President Barack Obama and his wife Michelle Obama as the epitome of true love, love didn't initially go his way. Before Barack got down on one knee to ask Michelle to marry him, he was interested in another woman
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‎In David J. Garrow's biography, "Rising Star: The Making of Barack Obama," the author reportedly reveals that the former president was once in love with Sheila Miyoshi Jager. Their relationship occurred while Barack was living in Chicago during his early 20s.
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‎Like the politician's mother, Jager, a woman of Dutch and Japanese descent, also studied anthropology. According to the book, the couple seemed like a natural fit, but the former anthropology student confessed to Garrow that their life together often felt isolating.
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‎According to Jager, their relationship was "an island unto ourselves," with Barack known to "compartmentalise his work and home life." At the time, Michelle's future husband worked as a community organiser and wrote fiction in his spare time.
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‎Yet even then, he already believed he would one day become president of the US. Garrow noted that she quickly recognised "a deep-seated need to be loved and admired" in him.
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‎Their relationship endured until marriage discussions began. Recalling how the proposal unfolded, Jager said, "In the winter of ‘86, when we visited my parents, he asked me to marry him."
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‎Her parents initially disapproved of the marriage, expressing concerns over Barack's professional prospects and feeling their daughter was too young. So, Jager told him "not yet," although they continued dating.
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‎A year after the proposal, Jager revealed that Barack's ambitions started to shift. She told Garrow, "I remember very clearly when this transformation happened, and I remember very specifically that by 1987, about a year into our relationship, he already had his sights on becoming president."
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‎Jager was one of the few people he confided in about that ambition. But when it was time for him to leave Chicago to attend Harvard Law School, their relationship was already deteriorating. Despite that, Barack asked her to go with him and suggested they get married.
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‎He made this second proposal even though he knew Jager was about to leave for a research trip to Seoul. She explained why she believed he proposed again. As Jager put it, the relationship stemmed "out of a sense of desperation over our eventual parting and not in any real faith in our future." Ultimately, the couple parted ways.
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‎Barack's former girlfriend earned her PhD in anthropology from the University of Chicago in 1994. She went on to become a professor of East Asian Studies at Oberlin College and has authored and edited four books on Korea and East Asia.
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‎Jager now serves as Chair of East Asian Studies and Chair of Russian, East European, and Eurasian Studies. She later married historian Jiyul Kim. While she has an Instagram account that describes her as a mother, author, and anthropologist, it contains no posts.
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‎Garrow's biography also explores other aspects of Barack's personal life. This includes the start of his relationship with Michelle during the 1990–1991 academic year. Despite dating Michelle, he continued to see Jager occasionally. Their contact eventually shifted to infrequent letters, especially as Barack's family life and political career began to take shape.
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‎Though their paths eventually diverged, Jager played a significant role in shaping Barack Obama's early years. Her story offers a rare glimpse into the personal journey behind the public figure.
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‎Barack & Michelle Obama Celebrate Daughter Sasha's Birthday with Stunning Family Photo, Igniting a Stir
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‎The former U.S. president and first lady marked a heartfelt occasion with a glimpse into their private life.
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‎Barack and Michelle Obama captured public attention with a rare family photo honoring their daughter Sasha's birthday. Set against a backdrop of sunlit terrain and rugged stone, the image revealed a relaxed, unified family moment — one that quickly sparked a mix of reactions online.
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‎On June 10, 2025, Michelle shared the photo on Instagram with a heartfelt message, "Happy birthday to my sweet girl, Sasha! Can't believe how quickly time has flown. I'm so proud of the woman you've become. Love you always! 💕🥳🎉"
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‎Barack echoed his wife's sentiments on Facebook, "Happy birthday, Sasha! Watching you grow into the incredible woman you are has been a true gift. I'll always be proud of you and will always be here for you."
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‎In the image, Sasha stands between her parents, dressed in a strapless cream top and flowing brown skirt with silver shoes. Michelle wears a sleek black dress and a yellow headwrap, while Malia, in a cream mini-dress, leans in towards her mother, holding a drink. Barack, in a white polo and gray trousers, smiles with his arm around Sasha's waist.
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‎The post quickly drew widespread attention, prompting a range of reactions. One critic remarked, "I have to say their daughters are beautiful. They don't look like their mother..."
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‎Others responded more warmly. "Wow, she grew up to be the hottest one in the family!" gushed one supporter. "Happy Birthday Sasha, a true fashionista!" one admirer commented. Another typed, "Beautiful ❣️...she looks like Official Chilli from TLC."
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‎"Wow. She's grown up to be a beautiful adult. Happy Birthday," one follower wrote. "OMG you guys are the most beautiful and smart and sweet family in the world," another person shared.
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‎"The prettiest first family ever ❤️," someone noted. "The most beautiful family💗," added another. "Only seems like yesterday those girls were little," a supporter reflected.
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‎From childhood moments in the White House to her most recent public appearance, Sasha's evolving style has always captured attention. Here's a look at how she continues to make a statement — then and now.
‎During a campaign rally on February 11, 2007, in Ames, Iowa, Sasha Obama, bundled in a red coat, rested on her mother Michell Obama's lap as Barack Obama addressed supporters at Iowa State University after launching his presidential run.
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‎Sasha sits with her parents, Michelle and then-Senate candidate Barack Obama, as they await election results on November 2, 2004, in a Chicago hotel room. Barack is widely expected to win his race against Republican Alan Keyes
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‎While attending the White House Easter Egg Roll on April 13, 2009, in Washington, D.C., Sasha — dressed in a black coat and blue headband —stood with a composed gaze as she observed the event from the South Lawn among guests and cameras.
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‎On election night, November 6, 2012, in Chicago, Illinois, Sasha Obama — dressed in a gray cardigan, green skirt, and layered necklaces — joined her father, Barack Obama, onstage to greet supporters during his second-term victory speech.