I had plenty of my own documents to contend with. And I didn’t need to be wowed. We were friends now, Barack and I, comrades in arms. We ate lunch out at least once a week and sometimes more often than that, always, of course, billing Sidley & Austin for the pleasure. Gradually, we learned more about each other. He knew that I lived in the same house as my parents, that my happiest memories of Harvard Law School stemmed from the work I’d done in the Legal Aid Bureau. I knew that he consumed volumes of political philosophy as if it were beach reading, that he spent all his spare change on books. I knew that his father had died in a car crash in Kenya and that he’d made a trip there to try to understand more about the man. I knew he loved basketball, went for long runs on the weekends, and spoke wistfully of his friends and family on Oahu. 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. My life in Chicago was nothing if not crowded with accomplished and eligible black women. My marathon work hours notwithstanding, I liked to socialize. I had friends from Sidley, friends from high school, friends developed through professional networking, and friends I’d met through Craig, who was newly married and making his living as an investment banker in town. We were a merry co-ed crew, congregating when we could in one downtown bar or another and catching up over long, lavish meals on weekends. I’d gone out with a couple of guys in law school but hadn’t met anyone special upon returning to Chicago and had little interest anyway. I’d announced to everyone, including potential suitors, that my career was my priority. I did, though, have plenty of girlfriends who were looking for someone to date.
One evening early in the summer, I brought Barack along with me to a happy hour at a downtown bar, which served as an unofficial monthly mixer for black professionals and was where I often met up with friends. He’d changed out of his work clothes, I noticed, and was wearing a white linen blazer that looked as if it’d come straight out of the Miami Vice costume closet. Ah well.
There was no arguing with the fact that even with his challenged sense of style, Barack was a catch. He was good-looking, poised, and successful. He was athletic, interesting, and kind. What more could anyone want? I sailed into the bar, certain I was doing everyone a favor—him and all the ladies. Almost immediately, he was corralled by an acquaintance of mine, a beautiful and high-powered woman who worked in finance. She perked up instantly, I could see, talking to Barack. Pleased with this development, I got myself a drink and moved on toward others I knew in the crowd.
Twenty minutes later, I caught sight of Barack across the room, in the grips of what looked to be an endless conversation with the woman, who was doing a large portion of the talking. He shot me a look, implying that he’d like to be rescued. But he was a grown man. I let him rescue himself.
“Do you know what she asked me?” he said the next day, turning up in my office, still slightly incredulous. “She asked if I liked to go riding. She meant on horseback.” He said they’d discussed their favorite movies, which also hadn’t gone well.
Barack was cerebral, probably too cerebral for most people to put up with. (This, in fact, would be my friend’s assessment of him when we next spoke.) He wasn’t a happy-hour guy, and maybe I should have realized that earlier. My world was filled with hopeful, hardworking people who were obsessed with their own upward mobility. They had new cars and were buying their first condos and liked to talk about it all over martinis after work. Barack was more content to spend an evening alone, reading up on urban housing policy. As an organizer, he’d spent weeks and months listening to poor people describe their challenges. His insistence on hope and the potential for mobility, I was coming to see, came from an entirely different and not easily accessible place.
There was a time, he told me, when he’d been looser, more wild. He’d spent the first twenty years of his