BeforeBarack Obama married Michelle, the 44th President of the United States had experienced some other significant romantic relationships.

Obama went even further and combined situations from different relationships, a strategy he called “compression.”

Garrow located Sheila Miyoshi Jager, a woman Obama had proposed to twice before meeting Michelle.

Barack Obama looking serious

For Jager, who was living with Obama, his shift in mindset was abrupt.

In 1986, Obama proposed to Jager while the couple visited her family.

Jager turned him down after her parents expressed doubts about Obama’s career and said she was too young.

Barack Obama giving a speech

race and identity," (viaThe Washington Post).

Garrow also references the political difficulties experienced by two African American U.S. senators from Illinois with interracial marriages.

The then-Michelle Robinson was his mentor, and soon they began dating.

Barack and Michelle Obama smiling

Six months later, they were contemplating marriage.

Then, at the beginning of 1990, Jager returned to the U.S. and accepted a Harvard teaching fellowship.

The couple would eventually marry and have three children.

Months later, Obama and Michelle got engaged.

After their marriages, Jager and Obama rarely corresponded.

In another instance, Obama called Jager to inquire if a biographer had communicated with her.