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46th Annual Legislative Conference Of The Congressional Black Caucus - Day 4

Source: Earl Gibson III / Getty

You may have heard that David J. Garrow is working on a biography about Barack Obama called Rising Star. In it, he alleges that a young Barack proposed to a woman named Sheila Miyoshi Jager. She turned him down not once, but twice, so he moved on and later met Michelle. The rest has become historic, if not legendary, relationship goals.

Admittedly, there was something about the news that got under my skin. At first, I wondered if she was Black (as if that matters…but she’s not, she’s Asian and white). Then I wanted to know if he might have loved her more than Michelle.

The Washington Post review of the book tried to paint a picture of Barack that pitted his heart against his political ambitions. Yes, Sheila was almost The First Lady, but as Brandy told us in her classic 1999 song , “Almost Doesn’t Count.”

After getting over the initial shock that we might never have been able to witness the love between Barack and Michelle, I had to wonder why this (unconfirmed) revelation bothered me.

Certainly, the societal dynamics of race and dating crossed my mind. Black women are told in a million little, and big, ways that we are the least desirable of women in the dating pantheon. We’re told that we are rarely, if ever, a man’s first choice–no matter how beautiful, intelligent, charming, or incredible we are. The framing of this story struck that nerve.

That nerve was yet again plucked by a related story on that implies Michelle may very well have been the first and only Black woman Barack ever dated, suggesting, of course, that he once preferred non-Black women. There’s literally no other reason to publish that nugget of information.

It was also alluded to in both pieces that the reason Barack decided to date a Black woman was because of the political capital it might bring him down the line. The suggestion here is that Michelle wasn’t good enough on her own to be his choice.

It’s suggested that she, as a Black woman, had to bring some sort  of ancillary value other than just who she is in order to be worthy of love or attention from a desirable man. All women of other races need to do to be chosen is just exist.

Heaven forbid that this Black man destined for greatness could pursue a Black woman just because there he was attracted to her. No, there had to be some added benefit for him to consider it. According to these accounts, Michelle was just window dressing for his ambition.

But, here’s the thing: None of this matters now if it ever did. It doesn’t matter what kind of women he dated before Michelle or even how many. Considering Barack’s family makeup and home life, it’s no surprise that he dated the rainbow.

As a biracial man, Barack grew up in mostly White or Asian spaces. Is it impossible to consider that perhaps there were just not as many Black women to choose from where he was when he started dating? Couldn’t his dating history have just as much to do with location and availability as it did his dating preferences?

But as we know, Barack was persistent in getting Michelle’s attention and ultimately they got married. That’s what matters.

It’s hardly uncommon thing to have more than one love or lover before you settle down. This particular case of the ex shouldn’t be any more significant. Everyone has a past. Barack may have had serious relationships before, but they all ended. They’re over. They’re canceled. They were done with a long, long time ago. Barack’s relationship with this ex–or any of his exes–are non-factors.

That’s why they were written out of Barack’s 1995 memoir, Dreams of My Father.

The truth is, Sheila might have been one of his great loves, but she was certainly not his greatest love. That would be Michelle.

No matter what Barack had with Sheila, he still married Michelle. After he met her, there was nobody else. He found The One. Period. That relationship should be respected, and there’s no reason to bring up old flames that have long since been snuffed out.

So, the next time we hear about Barack’s exes, we can pay them absolute dust because they’re failed romances are old, irrelevant news. If you were Sheila, would you want it to be known that you rejected Barack twice? She missed the ultimate come-up as well as a life with a man who spent eight years showing the world what loving not just Michelle, but three beautiful Black women, looked like.

So, who really missed out?

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Barack Biographer Claims He Proposed To Another Woman Before Michelle; But Why Is That Important? was originally published on

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23 thoughts on “Barack Biographer Claims He Proposed To Another Woman Before Michelle; But Why Is That Important?

  1. Dee Cee on said:

    Aww, somebody give Sheila a hug. Woulda, Coulda, Shoulda, but HE DIDN’T MARRY YOU FOOL. Get over it. Michelle is Mrs. Barack Obama.

  2. Doris on said:

    I don’t believe he asked her to marry him. She said he told her that he was concerned about the difference in races. If that’s true, why would he ask her to marry him. I think she just wants to be seen and heard. My son dated a woman from Japan and he ended the relation for the same reason. He did not want to deal with the madness and he did not want bi-racial children. When he told her , she went away and he never heard from her again. To bad this one could not have done the same thing.

  3. Many people date and/or marry others before they eventually find the love of their life. That’s how life works: Each decision and experience makes you better for the next. The same as President Obama had a chance to marry someone else before he met Michelle, I’m sure she had the same chance to marry someone else before she met Barack. In the end they seem equally yoked, they complement each other and they have been great examples of a powerful couple no matter what race and that’s the way it is!

  4. C.Robbins on said:

    It is not important! He knew what would it take to get his vision fulfilled! Men with a vision do it all the time! At the end of the day he chose the right one! Sometimes we should not even entertain certain stuff! Especially if it makes us look bad! So why even post this! Sure there something else we could focus on! Just saying!

  5. Sarah on said:

    Who cares. At the end of the day, He choose a SISTA. I rest for it to be this way than for a brotha o date sistas but marry a white woman. Obama still put a black woman by his side at the height of career and that love look REAL with their beauty black family

  6. hotlanta on said:

    I miss Michelle because if the foreigner First Lady says Vhite House one mo time Imma scream. Barak found someone blacker and smarter. Move on child.

  7. Passing Through! on said:

    White people can’t stand that fact Obama had a successful presidency in the wake of electing an incompetent, embarrassment fool like Donald Trump. He married a educated black women and became president. Michelle is first lady not white Shelia. Barack was born and raised in Hawaii, raised by whites so what’s so odd that he dated some white girl. The racist still trying to destroy hs legacy.

    • jhuf on said:

      You do know that if it weren’t for white people Obama would not have been president
      (not enough minoritys to vote him in)
      So where’s the logic in your “racist white people” remark?
      And if Trump is incompetent than more people especially AA’s should stride for that goal seeing as he’s one of the richest men in America

      • S.D. on said:

        He says he’s one of the richest….nonetheless, by the time he is out of office, he surely will be!!!!!

  8. jhuff on said:

    guess he wanted to get back to his WHITE roots but some say the past doesn’t matter so the past doesn’t matter…..I guess that go’s for everyone

  9. S.D. on said:

    …yet another distraction to take our focus off what is really going on in this country. Sheila who…..who gives a flying fig. Our focus needs to remain focused, hold the line and prepare to get our a##es out to vote in every single one of the upcoming mid-term elections. This is what is real.

  10. So what if he did. He upgraded to his queen Michelle. At least he haven’t been married 4 or 5 times like the clown in office.

  11. Diane on said:

    And so the s..t continues. Who gives a flying f..k about that dam book. It’s not how you start, it’s how you finish. Everyone has a past, yes that includes Barack. I don’t give a damn about what happened in his life 35-40 yrs ago. We have a damn fool getting ready to ruin this country, stripping ppl of healthcare and maternity care. and perhaps getting bombs dropped on us. Nobody gives a damn about this s..ty ass dirt bag book. Keep it moving. This fake prez has meetings with world leaders and forget their names. That’s the s..t we should be reading, and talking about.

    • Diane on said:

      Had Obama married a white woman he probably wouldn’t had won the presidency. A lot of blks may not have voted for him. Especially blk women. Besides, he made the right choice.

      • hotlanta on said:

        What do you mean especially black women. Black women don’t care if a black man is with a white woman. That old saying is played out as if we are jealous of white women and they are not jealous of us. That ole saying that we are jealous of their hair in reality their hair knots up, gets lice and smells like a horse when wet. That ole saying they have better bodies than black women. They are flat as a board. My last favorite they are smarter than black women. Stay Mad Abbey. We are living our lives by our own standards and rules and white women get mad when they are around us and are ignored by us because they have bought into the false reality that ALL black women wish they were them in reality we don’t.

    • Arthur Childress on said:

      @ Diane…..Great comment, and so on point! I must have missed this story. Btw, this is all alleged, the biography is unsanctioned.

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