At the beginning of their sophomore year, he met her friend Jen Buchholz, who was also learning CPR in preparation for a five-day Dartmouth wilderness trip. “I asked Jen who her friends are as a way of getting to know her,” he said. “When she said Ana Bowens, I let out this very guttural, ‘Oh, I dig her vibe.’” That night, Ms. Bowens, emboldened by a Keystone Light at a fraternity party, would do something that would stunt Mr. Schenk’s college dating experience.
“She put her hand on my chest, flicked her hair, and said, ‘So, I hear you dig my vibe,’” he said. Mr. Schenk was knocked sideways. “The moment she did that, I decided I wanted to learn everything I could about her as quickly as possible.” The start of a fierce campaign to become her boyfriend had begun.
At first, Ms. Bowens indulged it. When she wasn’t meeting him to study or hang out with mutual friends, she was answering his long, inquisitive emails. “I learned how ambitious and intelligent she was and that her mother and uncle are U.C.L.A. alumni,” he said. “When she told me she was Jewish, which is important to me, I was like, ‘OK, let’s wrap this up.’” His bid to cut the getting-to-know-you phase and move onto something more serious was premature.
Only three weeks into sophomore year, over a hangout on the futon in his dorm room, he asked her to a Portugal.the Man concert under the condition that she attend as his girlfriend. Ms. Bowens, taken aback, said no and left his dorm immediately. “I was freaked out,” she said. “It was way too much pressure.”
Over the phone, she told her mother what had happened. Judith Bowens was less alarmed by the boldness of her daughter’s suitor, then quick to recognize his plan. “I told her Benjamin was playing the long game,” Ms. Bowens said. “He wanted this to become something that would last.”