35. Wilmer Valderrama and Mandy Moore

Wilmer Valderrama and Mandy Moore had a very interesting relationship. They were basically kids since they first met when the singer and actress was just fifteen. They met again when she was 16. With their paths crossing constantly, Valderrama didn’t hesitate the second time around. He took a chance and asked the singer out.

Moore was one of the brightest stars in Hollywood during her teenage days. He was her first boyfriend; she never even kissed a guy yet not held hands with anyone special. Valderrama respected that about her but the two still grew apart to some degree, which caused their split. He later spread a false rumor about her, which she denied. According to the singer, it’s not like him at all and she just wondered where all of the lies came from. Valderrama apologized and the rest became a laughing childhood memory. Moore later admitted that she loved him and that they are now friends.