Prior to Barack and Michelle Obama's 26th anniversary, the former first lady shared
a photo from their wedding with the caption, "I can't imagine going on this wild ride with
anybody else." Neither can we! Nevertheless, they each did date these other people back in the day.
It would be very difficult, if not downright impossible, to picture the 44th First Lady
having been anyone other than 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, quote, "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.
As she wrote in her book:
"I knew he'd had plenty of girlfriends in the past, but didn't have one now [...] This
last bit was something I thought I could rectify."
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 historian David J. Garrow.
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. In one letter, the future President wrote:
"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."
By 1983, though, the couple's relationship was beginning to collapse. It would end shortly
after. Not long before the two split up for good, Obama wrote to her,
"When I see you, the palpitations of the heart don't boil to the surface."
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, 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.
"Take tips, gentlemen."
They began dating soon afterward. Cook is quoted as saying,
"I'm pretty sure we had dinner maybe the Wednesday after. I think maybe he cooked me dinner.
[...] 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. At the time, Cook wrote in her journal,
"I guess I hoped time would change things and he'd let go and 'fall in love' with me."
After almost a year of being single, Barack met Sheila Jager. Rising Star 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 Garrow's biography,
it's revealed that Barack proposed to Jager 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.
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.
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.
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.
Settling — especially for someone who wasn't as wonderful as her father — was just not
something Michelle was going to do.
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 even went to prom together. Upchurch
reminisced about his time dating Michelle, telling Enquirer,
"Michelle and I really liked each other, but you know how some high school boys are [...] 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. He went on to call the First Lady a, quote, "wonderful person."
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. While they were dating,
Michelle thought he was destined for medical school, but he ultimately decided to put his
schooling on hold to become a sports mascot.
Michelle admitted that she judged him for that decision and dumped him shortly after
witnessing him in the furry mascot outfit. As it turns out, things ended up okay for
Kevin. Michelle wrote that he did become a very good doctor and even married a fellow alum.
Michelle and Barack had their first kiss at a Baskin Robbins in the Hyde Park neighborhood
of Chicago. Michelle described the moment in her memoir, Becoming, writing,
"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."
Their relationship continued to progress shortly after the first kiss. Barack decided to propose
to Michelle on the same day as his bar exam. In 1992, the couple exchanged vows and became
husband and wife.
"For the past 25 years you have not only been my wife and mother of my children -- you have
been my best friend."
And with that, of course, all the rest is history.
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