The People Michelle And Barack Obama Dated Before They Met Each Other

Former President Barack Obama and First Lady Michelle celebrated another year of marriage in October 2018. "Happy Anniversary [Michelle Obama]," the former POTUS tweeted. "For 26 years, you've been an extraordinary partner, someone who can always make me laugh, and my favorite person to see the world with." Aww. In an equally adorable tweet, Michelle responded to her husband, thanking him for 26 years worth of "love, trust, and respect." She added, "Each day I'm with you, I'm reminded of what a treasure you truly are to us all." No, we're not crying, you're crying!


Several months prior to the couple's 26th anniversary, the former first lady also shared a photo on Instagram from their 1992 wedding. As part of a sweet tribute to her spouse, she wrote, "I can't imagine going on this wild ride with anybody else." To be honest, neither can we. Nevertheless, Michelle and Barack Obama did date other people back in the day. Who? Keep on reading.

Barack had "plenty of girlfriends in the past"

It would be very difficult, if not downright impossible, to picture the 44th first lady having been anyone other than the Michelle Obama. Had Barack and Michelle never dated, though, that very well may have been the case.


In her New York Times' bestselling memoir Becoming, Michelle revealed some of the first things she came to learn about her eventual husband. She knew that his father died in a tragic car accident in Kenya and that he read political philosophy books "as if it were beach reading." She knew that Barack enjoyed going for long runs over the weekend and had a love for basketball. Michelle also learned a little bit about his dating history. "I knew he'd had plenty of girlfriends in the past, but didn't have one now," she wrote. "This last bit was something I thought I could rectify." And that she did — eventually.

Barack's love for Alex McNear was "rich and plentiful"

While Barack was studying at Occidental College in Los Angeles, California, he wrote poems for a magazine run by a young woman named Alex McNear. When Barack relocated to attend Columbia in New York, he and McNear became "very close," according to Rising Star: The Making of Barack Obama by American historian David J. Garrow (via New York Post). In June 1982, they started seeing each other and when McNear went back to L.A. for school, the two carried on a long-distance relationship. In the early '80s, that meant lots of good old-fashioned hand-written letters.


"I trust you know that I miss you, that my concern for you is as wide as the air, my confidence in you as deep as the sea, my love rich and plentiful," wrote Barack in one letter. He was a poet, after all. By 1983, though, the couple's relationship was beginning to collapse. "When I see you, the palpitations of the heart don't boil to the surface," Obama wrote not long before the two split up.

He didn't "fall in love" with Genevieve Cook

Barack would end up meeting his next girlfriend at a Christmas party in 1983. According to an excerpt of the biography Barack Obama: The Story published by Vanity Fair, Genevieve Cook was a graduate student and second- and third-grade assistant teacher at a school in Brooklyn, though she was from Australia originally. The two stayed at the holiday party until well after midnight, talking and just generally getting to know each other. They began dating soon afterward. "I'm pretty sure we had dinner maybe the Wednesday after. I think maybe he cooked me dinner," Cook is quoted as saying. "Then we went and talked in his bedroom. And then I spent the night. It all felt very inevitable."


The two dated until spring 1985 and although the relationship was Barack's most serious yet, it seems Cook was more invested. "I guess I hoped time would change things and he'd let go and 'fall in love' with me," Cook wrote in her journal at the time. 

Barack proposed to Sheila Jager twice

After almost a year of being single, Barack met Sheila Jager. Rising Star (via New York Post) revealed that she and Barack became close in the subsequent months and decided to move in together. After only dating for four months, they started talking about marriage. In the biography, Jager revealed that Barack proposed in the winter of 1986, while they were visiting her family. But there was a problem: Barack and Jager's Republican family didn't exactly mesh well. According to Barack's ex, Barack and her father argued over politics and he did not give the couple his blessing. 


Still, Barack and Jager continued their relationship. By 1987, Jager said Barack had transformed into a "powerfully ambitious person" who "already had his sights on becoming president." However, in May 1988, the couple's relationship was fairing badly. According to Jager, she'd read Barack's journal and saw that he'd written about someone else. Although she moved out at that time, they continued to date. Barack even proposed once more just before leaving for Harvard, but Jager turned him down.

Michelle didn't have "too many long-term boyfriends"

In an interview with ABC News, Michelle Obama's brother, Craig Robinson, compared their family to the Cleaver family from the mid-century television show Leave It to Beaver. He explained that their hardworking parents taught them to both have respect for others and for themselves. "We always said that peer pressure didn't mean anything if you had Fraser and Marion Robinson pressure," he explained. "And a black version of the Cleavers, no less." Through their parents' example, the Robinson children also learned the importance of having high standards. 


Perhaps that's why Michelle didn't have much interest in serial dating. Although her brother made it his job to keep an eye on his baby sister when it came to who she dated, he admitted, "My sister never had too many long-term boyfriends." Settling — especially for someone who wasn't as wonderful as her father — was just not something Michelle was going to do.

Michelle "really liked" David Upchurch

Michelle may not have been willing to get serious with just anyone, but that didn't mean she swore off dating altogether. In the early 80s, when Michelle was between 16 and 17 years old, she started seeing David Upchurch. The couple went to prom together, but unfortunately Upchurch wasn't able to remember many details about the date when speaking with Enquirer (via The Telegraph). Thankfully, he does remember dating the young woman who would one day become a first lady. Because, how could you not?


"Michelle and I really liked each other, but you know how some high school boys are," he told the publication. "We're not ready to be responsible and we screw up." At that point in time, he admitted he wasn't thinking much about the future or what he wanted out of life. "But Michelle knew what she wanted, and after graduation she was off to Princeton," said Upchurch. "I couldn't stand in her way. I wished the best for Michelle because she's always been a wonderful person."

Michelle and the jock named "Kevin"

In Michelle Obama's memoir Becoming, she reminisces about Kevin, a college senior and the "football-player boyfriend" she dated during her sophomore year at Princeton University. Originally from Ohio, Michelle described him as "a near-impossible combination of tall, sweet, and rugged." Ooh la la. While they were dating, Michelle thought he was destined for medical school, but he ultimately decided to put his schooling on hold and "pursue a sideline interest in becoming a sports mascot." Umm. Michelle admitted that she ("unfairly") judged him for that decision and dumped him "as soon as [she'd] seen him in a furry mascot outfit."


Although Kevin has yet to come forward about his relationship with Michelle, we do know how things ended up. Michelle wrote that Kevin did become a "very good" doctor after all and even married a fellow alum. And, well, you know who Michelle ended up marrying.

The rest is history

"As soon as I allowed myself to feel anything for Barack, the feelings came rushing — a toppling blast of lust, gratitude, fulfillment, wonder," Michelle Obama wrote in her memoir (via Entertainment Tonight). "Any worries I'd been harboring about my life and career and even about Barack himself seemed to fall away with that first kiss, replaced by a driving need to know him better, to explore and experience everything about him as fast as I could." Their relationship continued to progress after their first kiss at Baskin Robbins.


Barack Obama decided to propose to Michelle on the same day as his bar exam — talk about pressure! Fortunately for Barack, Michelle said yes. In 1992, the couple exchanged vows and became husband and wife. And with that, of course, all the rest — the woman to whom Barack scribbled love notes, the ex Barack nearly married (twice), the boy Michelle "really liked," and that "tall, sweet, and rugged" football-playing boyfriend — is history.