During a White House lunch in February, the President quizzed the PM about younger brother Nick, who died of cancer aged 60.
According to The Spectator mag, he asked: "Your brother, Keir…he died…was it a good death?"
Instead of replying in full, Starmer steered the conversation back to lowering car tariffs.
Sir Keir's team said Trump was "obsessed with death", it was claimed.
The revelations came as Trump — a guest at Hugh Hefner's Playboy mansion during his 2016 presidential bid — signed his "big beautiful Bill" into law.
It enacts key parts of his agenda including tax cuts and an immigration purge.
US President Donald Trump said Russia just wanted to -keep killing people- and hinted at sanctions after Moscow launched its largest ever drone and missile attack on Ukraine in the three-year-old war-
TRUMP RAGE
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US President Donald Tump is said to have grumbled about his lack of access to porn in the White HouseAP