Barack Obama’s Surprising Dating History Before He Met Michelle

One of the things we’ve often written about is the strong marriage between Barack Obama and Michelle Obama. These two were the absolute portrait of grace and love while Barack served two very successful terms as president. Now, this ultimate power couple has leveraged their influence into extreme wealth, and they get to spend much more time together now than when they were living in the White House. 

As hard as it is to believe, though, this power couple came close to never getting together in the first place. That’s because Barack had a string of women in his life before he met Michelle, including another woman that he nearly married. Just what is this former president’s dating life like, and what does it tell us about the real Barack Obama? Keep reading to find out!

The senior prom date

Some of Barack Obama’s previous girlfriends are a bit more shrouded in mystery than others. For example, we don’t know too much about Meghan Hughes other than the fact that he took her as his date to senior prom back in 1979. They didn’t become a serious item or anything, but it is still significant that Obama asked her out in the first place.

Why’s that significant? Well, as this article will make abundantly clear, Barack Obama has never had trouble finding girlfriends. The charm and wit he exhibited as president was on full display  back in high school, and we’re willing to bet any woman he asked out would have said “yes.” In this case, Hughes has the distinction of being the first significant female friend of Obama (at least, that we know about), but she most certainly wouldn’t be the last.

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The first real relationship

Who, then, was Barack Obama’s first serious girlfriend? That honor goes to Alex McNear. They met when both were attending Occidental College. Sadly, things didn’t work out after Barack transferred to Columbia University, though he made a very impressive effort to keep their long-distance relationship alive.

How much effort are we talking? As the New York Post reports, Obama’s love letters could get pretty steamy. “When I see you, the palpitations of the heart don’t boil to the surface,” he wrote. “I care for you as yourself, nothing less but also nothing more.” As you can tell, the future president had pure charisma long before he landed in the White House!

The lover turned roommate

After he broke up with Alex McNear, it didn’t take Barack Obama long to find another girlfriend in the form of Genevieve Cook. She wasn’t just some rebound, though…things got serious enough for the two to move in together. They shared an apartment, and it sounds like Cook really enjoyed her time living with the future president.

According to the New York Post, Cook was impressed by her boyfriend’s mind. She wrote in her journal “I have not experienced the kind of intellectual stimulation Barack offers me since I left college.” Sadly, things didn’t work out between them (largely because she was more invested in the relationship than him), but the next girlfriend was one that Obama nearly married before ultimately meeting Michelle.

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The woman he almost married

After breaking up with Genevieve Cook, Barack Obama’s next serious girlfriend was Sheila Jager. And we do mean serious: while he didn’t mention her by name, Obama wrote about Jager in his book Dreams From My Father, writing, “hidden and warm. Your own language. Your own customs. That’s how it was.”

Things were so serious, in fact, that Obama proposed marriage to Jager on two different occasions. The first time, she didn’t tell him no but “not yet” as a result of her parents thinking she was too young to get hitched. And it didn’t help that Obama had very different politics from Jager’s father, causing them to fight. Later, Obama proposed again, but both of them knew it was a desperate move to try to save a failing relationship. She declined again and the two broke up for good.

Michelle Obama: the one who almost got away

All of this leads to the true love of Barack Obama’s life: his wife, Michelle. The two met when he began working at her prestigious law firm, and they had a common culture because they had both gone to Harvard. However, Michelle was actually his mentor at the firm and was understandably hesitant to start a relationship with the new hire. He kept asking her to go on a date, but she kept declining because she feared a relationship would be tacky.

Eventually, Barack made the grand gesture of offering to quit the law firm if it meant he could finally date Michelle. She then relented enough to let him take her out for ice cream after an office BBQ party. That was in the summer of 1989, and the two got married in 1992. The rest is history, and decades later, they remain America’s ultimate power couple.

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