The Sneaky Way Bill Gates Tried To Meet Girls While In High School

Microsoft co-founder Bill Gates has spent decades carefully curating the perfect image of America's lovable, sweater-toting billionaire with an appetite for philanthropy — and while he's seen his fair share of controversy — he isn't especially known as a cunning schemester. Long before Gates became a software sensation whose name ascended to the uppermost ranks of Forbes' billionaire's list, he was a shy kid enrolled at the exclusive Lakeside School in Seattle. At Lakeside, 13-year-old Gates discovered a love of programming that would start him down the path from teen-geek to multi-billionaire businessman.

Gates wasn't exactly a ladies' man in school. He was small for his age, bullied as a child, and by all accounts, he spent most of his time logging long hours on his school's teletype terminal, a screenless predecessor to the personal computer. Gates may not have had the brawns — but he had brains — and he used them to meet girls in a seriously sneaky way. 

These days – with a fortune valued at $130 billion – Bill Gates can usually get his hands on just about anything he wants, but back in high school it was a different story, especially as a young nerd with an ineptness at speaking to girls.

At Lakeside, Gates continued to improve his technological expertise. At one point, he and three other students had their computer privileges revoked after they were caught taking advantage of a software glitch that enabled them to obtain additional computer time. After the ban was lifted, Gates and his pals offered to help find bugs in the computer company's software in exchange for screen time, but it wouldn't be the last time Gates twisted his privileges.

While Gates failed to attract the attention of female classmates, his proficiency with Lakeside's teletype terminal caught the eye of school administrators. School officials tasked Gates — along with his pal and future Microsoft co-founder Paul Allen — to code software that would digitize the entire school's scheduling, an exhausting task that could take all summer to do manually.

Bill Gates — then in charge of Lakeside's scheduling with Paul Allen — cooked up an ingenious scheme to meet girls at Lakeside. Gates told the BBC that they enrolled him into classes where there would be a disproportionate number of interesting girls. "Paul did the computer scheduling with me. Unfortunately for him, he was two years ahead of me and he was off to college by then. So I was the one who benefited by being able to have the nice girls at least sit near me," he explained.

Unfortunately, the scheme didn't exactly pan out the way Gates had hoped. While he succeeded in hacking his way into classrooms filled with young bachelorettes, he still lacked the skills to approach them. "It wasn't that I could talk to them or anything — but they were there. I think I was particularly inept at talking to girls, or thinking, 'OK — do you ask them out, do you not?'