The 25-year-old singer admitted the first female to catch his eye was the former 'Friends' actress.
Asked by Ellen DeGeneres during a game of 'Burning Questions' who his first crush was, he said: ''Probably Jennifer Aniston.''
The 'Watermelon Sugar' hitmaker had his first real kiss before he was a teenager.
Asked when he had his first kiss, he replied: ''Like, kiss kiss? 12 I think.''
Harry was very candid during the quickfire questioning, admitting he isn't currently dating anyone and there are certain attributes he's attracted to in a woman.
He added: ''Eyes, smile, character.''
But the former One Direction hunk needed clarification on some questions.
Asked if he prefers boxers or briefs, he said: ''What shape is a brief? Boxers are like the swimming short? Briefs.''
He later alluded to the question again when asked what he'd call his signature fragrance.
He quipped: ''Boxers or Briefs.''
The 'Sign of the Times' hitmaker hinted at a naughty side when he confirmed he'd been in handcuffs and sparked laughter from the audience when asked what his guilty pleasure is.
He confessed: ''Working out to One Direction.''
Fans also learned from the segment that Harry would like to be a florist if he wasn't a pop star, he's forgotten his lyrics on stage and his all time favourite music video is 'Sledgehammer' by Peter Gabriel.
The British popstar confessed to fearing the end of his life.
Asked his biggest fear, he admitted: ''Dying. That was dark.''
Harry recently admitted he doesn't mind being asked about his sexuality but insisted he has no plans to definitively provide an answer.
He explained: ''What I would say, about the whole being-asked-about-my-sexuality thing - this is a job where you might get asked. And to complain about it, to say you hate it, and still do the job, that's just silly. You respect that someone's gonna ask. And you hope that they respect they might not get an answer.
''It's not like I'm sitting on an answer, and protecting it, and holding it back. It's not a case of: I'm not telling you cos I don't want to tell you. It's not: ooh this is mine and it's not yours. It's: who cares? Does that make sense? It's just: who cares?''
They might sound like they're from the 70s, but they way they roll is very 2020.
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