Aniston, who is currently engaged to Justin Theroux, dated Tsilimparis when she was just 12-years-old, the New York Daily News reported.
Tsilimparis still keeps the Valentine's Day card that Aniston gave him 30 years ago. "Dear Adonis. Love & Friendship Always. Jennifer A," the card reads.
Now working as an author of musical scores for TV and film, the New Yorker said that the two youngsters used to sneak behind a school staircase to "make-out".
"She was very open, very, very sweet. She was very, very loving, and she had a very big heart," Adonis said, adding their romance got no further than kissing.
"I tried. But she didn't let me.. .We used to go to the back stairs at school at lunchtime and make out... She was just goofballs... But that's why I loved her. Total clown, very lovable and that's why everybody liked her," he said.
Tsilimparis does not remember how the young couple split but classmate Tom Friedner, who also had a brief romance with the star, said that it was Tsilimparis who ended it.
"I remember the day they broke up. I can't remember exactly why, but Adonis initiated it. He couldn't tell her himself, so he had another friend, Ben, tell her and I remember Ben in the hallway just walked up to Jennifer and said, 'Jennifer, Adonis doesn't want to date you anymore'. And she said, 'Okay, fine'. I can't remember exactly why though," Friedner said.