Obama: Office Romance
If only most people were lucky enough to get so much out of a summer job. After Obama's first year at Harvard Law, Sidley & Austin, a large corporate law firm in Chicago, hired him as a summer associate. In what he has called the luckiest break of his life, Michelle Robinson (who worked in the intellectual-property group specializing in entertainment law) was assigned as Obama's adviser. His first impression of Michelle was, as he recounted in The Audacity of Hope, that “she was tall — almost my height in heels, and lovely, with a friendly professional manner that matched her tailored suit and blouse.” Michelle, meanwhile, later told the Washington Post that she had heard his “strange name” and assumed that “any black guy who spent his formative years on an island had to be a little nerdy, a little strange.” “I already had in my mind that this guy was going to be lame,” she told Ebony.
But the presumed dork turned out more attractive than the photo he’d sent in, and he was confident, easy to talk to, and had a good sense of humor. About a month into the summer Obama asked her out, but she declined. “I thought, 'No way.’ This is completely tacky,” Michelle told ABC. “This is my first summer. I've got an advisee and I'm gonna date him? I thought, 'No, no, I can't do that.’ And he was like, 'No one cares.’" Obama kept at it, and even threatened to quit if it meant he could romance her. “Eventually, I wore her down,” he writes. One day, after Michelle drove him home from a business picnic, they went to the Baskin-Robbins across from his place and sat together on the curb eating ice cream. “I asked if I could kiss her,” he remembers. “It tasted of chocolate.” On their first formal date, the pair saw Spike Lee’s Do the Right Thing, where Obama, as he later bragged, was allowed to touch Michelle's knee. Lee told New York that he later told Obama, “Thank God I made [Do the Right Thing]. Otherwise you would have taken her to Soul Man. Michelle would have been like, ‘What’s wrong with this brother?’” Indeed, Michelle later told ABC it proved “he was down socially.”
Romney: High School Party
When Romney was a Cub Scout, out with friends from his troop, he remembers seeing a girl riding up on a horse. As the laws of prepubescent boy-girl interactions dictate, the boys threw rocks at her. The girl, Ann Davies, was the mayor's daughter in Bloomfield Hills, the wealthy Detroit suburb where Romney grew up. Perhaps that's why Romney never made a move. By the time they properly met, on March 21, 1965, at a mutual friend's party where 45s of the Beatles and the Rolling Stones provided the soundtrack, Romney was a senior at the all-boys Cranbrook high school and Ann a sophomore at all-girls Kingswood. Mitt gave her a ride home that night, though she remained, by her own confession, "aloof" to his early advances. "He was one of those guys that would date a girl for like six weeks and then go on to another girl, and then another and another," she told Newsmax in 2007. "He kind of did that through my sophomore year. He dated about three of my friends. So I was very wary of him." A little while later she acquiesced to a proper date. Romney showed up in his red Marlin — produced by American Motors, which his father headed up at the time — which he'd buffed and shined just for the occasion. Classy young man that Romney already was, he brought along a bottle of sparkling Catawba grape juice and two chilled glasses as an aperitif before they headed off to see The Sound of Music. Barely months later, in June, Romney took Ann to his senior prom and asked her to marry him. Though it would ultimately take a few extra tries before Ann finally said yes, the couple chose to get married on March 21, 1969 — four years after they properly met, not including the rock-throwing incident.