He previously attended Rugby School, which is regarded as one of the top schools in England.
So Barack Obama presumably had little to say when pictures emerged of Malia, 19, locked in a clinch with a young man identified as Rory Farquharson, a British public schoolboy studying at Harvard.
Rory Farquharson caused an global media storm on Saturday (18 November) when he was caught on camera making out with former President Barack Obama's eldest daughter.
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Malia took a gap year before attending Harvard, meaning she is the same age as Rory.
The head boy position, which is typically selected by the school principals, provides links between teachers and students. Farquharson was evidentially considered "quite a catch" there, and he was known to play golf and rugby.
Mr Farquharson began his studies at the university a year ago after completing his A-Levels, posting a picture of himself at the campus with the caption: "So it begins".
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"He was very popular", the insider added.
The 19-year-old was also part of the Blue Bunsen Society, a chemistry club.
But teen Rory doesn't follow Barack Obama on Twitter - instead following President Trump.
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Another photo shows Malia smoking a cigarette during the tailgate - a sign that she may be picking up her dad's old tobacco habit.