Obama proposed twice to a woman he continued to see while dating Michelle, here's what we know

Barack Obama’s name is on everyone's lips as a letter from the former president to ex-girlfriend Alex McNear reveals he regularly imagined making love to men. The New York Post obtained the letter, which dates back to November 1982, when Obama was 21. He writes:

In regard to homosexuality, I must say that I believe this is an attempt to remove oneself from the present, a refusal perhaps to perpetuate the endless farce of earthly life. You see, I make love to men daily, but in the imagination.

It turns out that Obama’s love life is a rich tapestry ofinteresting stories like this one. Let’s take a look at the woman who came before Michelle… or did she?

Who is Sheila Miyoshi Jager?

According to the biography Rising Star: The Making of Barack Obama, written by award-winning historian David Garrow, Jager and Obama were deeply in love in the 1980s. They lived together, and Jager described them as being ‘an island unto themselves’.

How many times did Obama propose?

The first time Obama proposed, Jager turned him down because her parents thought they were too young. The biography claims that Jager, now an Oberlin College associate professor, recognised a ‘need to be loved and admired’ in her partner. Obama had big dreams; one year into their relationship, in 1987, he had already decided he wanted to become president.

Obama allegedly believed he needed to identify fully and authentically as an African American and feared that having a non-African-American partner - Jager is of Dutch and Japanese heritage - would damage his image in this respect.

Although this reportedly took a toll on Jager and Obama’s relationship, the former president was not ready to give up and proposed again, asking Jager to join him at Harvard Law School.

When did Michelle come into the picture?

Jager and Obama reportedly broke up following Jager’s rejection of this second proposal. Mail Online reports that she feared his offer came from 'a sense of desperation over [their] eventual parting’ and was not the result of ‘any real faith in [their] future.'

Obama went to law school where he famously met and started dating Michelle. However, Garrow claims that Jager and Barack continued to see each other on and off after his former girlfriend arrived at Harvard for a teaching fellowship.

Read more: Barack Obama opens up about marriage problems while he was in office

Was Obama popular at Harvard Law School?

According to Garrow, no. It seems Obama had a bad habit of expressing his opinion whether someone had asked for it or not. The New York Post reports that one student told Garrow:

In law school, the only thing I would have voted for Obama to do would have been to shut up

The biography also suggests that the former president considered entering into a relationship with an openly gay male professor, Lawrence Goldyn, who was generally loved by students and had ‘made a huge impact’ on Obama.

However according to Garrow, he decided against it and later told a girlfriend that he had ‘considered gayness but ultimately decided that a same-sex relationship would be less challenging and demanding than developing one with the opposite sex’.

Despite his colourful past, the former president and his wife Michelle seem to live a happy life together with their two daughters,Malia and Sasha. The couple will celebrate their 31st wedding anniversary on 3 October and probably laugh together about the antics of their younger selves.

Read more:

⋙ Michelle Obama Speaks Out About the Rough Times During Her Marriage

⋙ Donald Trump: Legal experts claim he could be disqualified from running for President

Sources used:

New York Post: Obama ex gushed about 'all this f—ing'

Mail Online: REVEALED: Barack Obama two-timed Michelle Obama with a white girlfriend he had 'desperately proposed to TWICE'