Obama's Embarrassment About His 'Wildly Pretentious' Love Letters In College Is All Of Us

"I should've tried like, you know, wanna go to a movie or go on a picnic?"

An interview with President Obama would be the highlight of many a journalist's career, but when David Axelrod, a close former staffer, sat down with the president for his podcast, The Axe Files, the vibe likely resembled more a chat between old friends than anything. 

Their extensive conversation touched on many topics, including the election, Obama's post-presidential plans, and his love for his mother. But Obama also revealed to Axelrod that, contrary to what Michelle Obama has said about his swag, the president wasn't always smooth on the romance front. 


Axelrod wondered how Obama transformed from "a guy who enjoyed a party and was kind of a goof-off" when he studied at Occidental College to a much more purposeful, disciplined person after transferring to Columbia University. Obama said that it came with the gradual shift towards being more socially conscious. 

But brooding about serious issues also made Obama "wildly pretentious," he recalled. And the love letters he wrote to young women he was courting? "Impenetrable," he said. 

"When I read back old journals from that time, because I'm starting to write, or letters that I've written to, you know, girls you're courting or something, they're impenetrable," Obama told Axelrod. "I don't understand what I'm saying, right? There's all kinds of references ... and I'm like what — what are you talking about?"

Those pickup lines, Obama said, didn't work so well. "People were all like wow, this guy is just too intense. He needs to lighten up," he added. "I should've tried like, you know, wanna go to a movie or go on a picnic?" 

It seemed that Obama learned his lesson afterwards. As a young community organizer, Obama and Michelle went to see Spike Lee's Do The Right Thing in theaters on their first date.

And years later, Michelle provided the support that Obama relied on while he pursued a career in politics despite her reluctance. He told Axelrod:

I was also married to a woman who was not going to put up with any foolishness, and you know, Michelle, I can't underestimate the degree to which having a life partner who is so grounded and so strong and steady and fundamentally honest helped. 


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