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

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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