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Adonis Tsilimparis, Jennifer Aniston’s first boyfriend, speaks out about their high school relationship

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Jennifer Aniston’s first boyfriend, Adonis Tsilimparis, has spoken out about his fleeting high school relationship with the Hollywood star.

Jennifer Aniston might have dated a string of the world’s most desirable men, including Brad Pitt and John Mayer, but musician Adonis Tsilimparis was the first man to pucker up with the A-list actress.

It might have been over 30 years ago, but the seventh grade romance between the 12-year-olds is still fresh in his memory, and he even has a Valentine’s Day card to prove it.

“Dear Adonis,” Jennifer Aniston had written.

“Love & Friendship Always. Jennifer A.”

Now working as an author of musical scores for TV and film, the New Yorker told the New York Daily News 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 Tsilimparis told the paper.

Jennifer Aniston's first boyfriend, Adonis Tsilimparis, has spoken out about his fleeting high school relationship with the Hollywood star

Jennifer Aniston’s first boyfriend, Adonis Tsilimparis, has spoken out about his fleeting high school relationship with the Hollywood star

Adonis Tsilimparis went on to claim that, although he had tried, he hadn’t got any further than kissing with the now superstar: “I tried. But she didn’t let me…We used to go to the back stairs at school at lunchtime and make out.”


Even though Jennifer Aniston, 43, is now happily engaged to actor Justin Theroux, her first boyfriend still remembers her fondly.

“She was just goofballs…But that’s why I loved her. Total clown, very lovable and that’s why everybody liked her,” Adonis Tsilimparis said of the actress.

While he went on to say that he didn’t remember how the young couple split, classmate Tom Friedner, who also had a brief romance with Jennifer Aniston, said that Adonis Tsilimparis ended it.