“There are all these subtle sci- fi jokes and references to ‘Star Trek’ and ’70s pop culture,” she says. “It was just so weird and different. I felt like I was reading somebody who had my exact same sense of humor.”
By the time she finished the chapter, Sproul, then 23, had a major crush, though she had no idea what Latimer looked like, or whether he was single or straight. When he came into the office of the Ross Yoon Agency in early 2009, she eagerly met him at the door and offered to fetch lunch.
Latimer briefly took note of the outgoing blonde before returning his focus to the manuscript. He was 37 and had come to the conclusion that he was likely to remain a bachelor. “I had been in a couple serious relationships. I had dated women. It just didn’t work out,” he says. “I just felt like my time had passed.”
When Latimer’s book sold, his agent suggested he hire Sproul as a freelance editor. She dressed up for their first editorial meeting and sent him chatty e-mails as she worked through the draft. He registered none of her interest and wore gym clothes to their next meeting in Shirlington. But when she suggested they go have a beer to celebrate the book’s completion, he agreed.
One beer turned into two and Sproul ramped up her flirtations. They giggled at their shared sense of humor and idiosyncrasies. “We’d both been sort of fat, awkward kids who lost significant amounts of weight,” she says. “We discovered a mutual love of eating frozen Cool Whip, which I’m sure is just frozen chemical. But you can eat the whole tub and it’s, like, 30 calories.”
He remained oblivious to her overtures until she leaned her head on his shoulder before going to the bathroom. Then he was just confused. They continued their evening at the grocery store, bonding over other favorite low-calorie food, and then she drove him home. He said good night without so much as a hug. “I was like, ‘Oh my God, he doesn’t like me!” recalls Sproul.
The next day, Latimer called his best female friend, Amber Roseboom, for an assessment. “Things like that go over his head,” Roseboom explains. “With Anna, he just couldn’t believe that she would be so genuinely interested in him. It actually speaks to his humility.”
Despite Roseboom’s reassurance, Latimer remained unconvinced. He sent Sproul occasional text messages, but when she invited him to a happy hour at the Cato Institute that April, he said he was going on a blind date. “But if it’s the disaster it usually is, I’ll give you a call,” he promised. The date was abysmal, but he neglected to follow up with Sproul.
A few days later he texted asking, Do you like shrimp? Sproul screamed with frustration and marched into the office of Latimer’s agent, Howard Yoon, to ask what she should make of the mixed messages.