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Politics

Before Michelle, Barack Obama Proposed to Another Woman—Twice!

Published on: February 21, 2025 at 7:15 AM ET

Before Barack Obama met Michelle, he was in love with someone else and proposed to her twice.

Divya Verma
Written By Divya Verma
Senior Editor
Kanika Saini
Edited By Kanika Saini
Senior Editor
Barack Obama and Michelle Obama
Michelle Obama is not the first woman Barack Obama proposed. (Image Credit: X/@timecaptales/@Only4RM/@VanLathan)

Barack Obama and Michelle Obama are one perfect couple. They both are intelligent and charming people. They possess great knowledge and have a way with words that everyone wants to listen to them talk. However, this perfect couple may not have even met if Barack’s first love didn’t end in heartbreak.

The book titled Rising Star by David J. Garrow explores the relationship between Barack Obama and his first love, Sheila Miyoshi Jager. Both of them met while Obama was in Chicago.

Sheila Jager
Shiela Jager is an associate professor at Oberlin College (Image Credit: Oberlin College)

Obama’s biography, My Father’s Dreams, has no mention of Ms. Jager; however, Garrow stresses the relationship and its importance in framing Obama’s formative years as a young adult.

According to the book, Barack Obama and Sheila met in the mid-1980s and were in a long-term relationship. By 1986, Barack was completely smitten by his lady love and planned to propose to her. He even met her parents with this intention.

This bit paraphrased from David Garrow’s biography of Obama is burned into my brain. It describes the unraveling of his relationship with Sheila Jager, a woman he wanted to marry, as he began to believe that having a white wife was a major political liability. pic.twitter.com/C13X6khmK2

— Sturgeon’s Law (@Sturgeons_Law) May 3, 2020

However, Ms. Hager’s parents had their reservations as the couple was fairly young and had yet to make their mark. Ms. Jager is of Japanese and Dutch descent, though she does not believe that had anything to do with her parent’s rejection.

Ms. Jager tells Garrow that after the initial proposal, there was a shift in Obama. As the days went by, he became ambitious very quickly. He also wanted to explore his African-American heritage and dreamt of being the president even then.

His growth and change in personality were getting in between the couple, and Sheila could feel Barack moving away from him. As he harbored a political dream, Jager started to wonder if Barack thought a woman of African descent would be more suitable to be his wife. She added that Barack Obama also needed to be admired and loved in a sense that she was not able to.

On February 6th, 1990, Harvard Law Review elected 28-year-old Barack Obama as their first black president.

30 years ago. pic.twitter.com/pIWd6ztXqt

— UberFacts (@UberFacts) February 6, 2020

All this started to put a strain on the relationship, and as Barack planned to move to Harvard, the relationship was held by a thread. However, Barack proposed to Ms. Jager once again. But she believes it was not for the sake of love and the future but due to despair of a broken relationship. Considering this, she rejected the proposal again.

Once Barack moved to Harvard Law, he met Michelle Obama and went on to date her. However, he could not completely get over the breakup with Sheila. They stayed in touch for almost a year after he dated Michelle when Ms. Jager moved to Harvard on a teaching fellowship. 

Once Barack Obama married Michelle, that’s when Ms. Jager moved out of his life completely. The communication remained limited to letters and occasional phone calls.

Now 53, Ms. Jager is an associate professor at Oberlin College in Ohio. She is also a director of the East Asia program at the college.

TAGGED:Barack ObamaMichelle Obama
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