The sneaky way Bill Gates tried to date girls in high school

Microsoft co-founder Bill Gates has spent decades meticulously curating the perfect image of America’s loveable billionaire with sweaters and an appetite for philanthropy — and while he’s seen his fair share of controversy — he’s not particularly known as a cunning schemer. Long before Gates became a software sensation whose name climbed the top ranks of Forbes’ billionaires list, he was a shy boy enrolled at Seattle’s exclusive Lakeside School. It was at Lakeside that 13-year-old Gates discovered a love of programming that would take him from teenage geek to multi-billionaire businessman.

Gates wasn’t exactly a womanizer at school. Small for his age, he was bullied as a child, and by all accounts he spent most of his time logging long hours on his school’s telex machine, a screenless predecessor of the personal computer. Gates might not have the brawn — but he had brains — and he used it to hit girls in seriously sneaky ways.

Bill Gates was a young genius

These days — with a $130 billion fortune — 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 a disability with girls to speak.

At Lakeside, Gates continued to improve its technological know-how. At one point, he and three other students had their computer privileges stripped after they were caught exploiting a software bug that allowed them to gain extra computer time. After the ban was lifted, Gates and his cronies offered to help troubleshoot the computer company’s software in exchange for screen time, but it wouldn’t be the last time Gates twisted his privileges.

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While Gates failed to attract the attention of female classmates, his proficiency with the Lakeside teletypewriter caught the attention of school administrators. School officials tasked Gates — along with his sidekick and future Microsoft co-founder Paul Allen — with programming software that would digitize all school planning, a tedious task that could take all summer to do manually.

His technical understanding could not hide his social clumsiness

Bill Gates – then responsible for planning Lakeside with Paul Allen – came up with an ingenious plan to meet girls in Lakeside. Gates told the BBC that they put him in classes where there would be a disproportionate number of interesting girls. “Paul did the computer planning with me. Unfortunately, he was two years ahead of me and he was in college by then. So I was the one who benefited from the fact that the nice girls could at least sit near me,” he explained.

Unfortunately, the plan didn’t go exactly as Gates had hoped. While he did manage to hack into classrooms full of young bachelorette girls, he still lacked the skills to approach them. “It wasn’t like I could talk to them or anything — but they were there. I think I was particularly incapable of talking to girls or thinking, ‘Okay – you ask her out, don’t you?’