Moakler and De La Hoya became engaged prior to the 1999 birth of their daughter, Atiana Cecilia De La Hoya (born March 29, 1999).
Moakler has said "it wasn't a planned pregnancy, but it was understood if it happened it was beautiful and if it didn't that was fine too." In December 2000, Moakler filed a .5 million palimony suit against her ex-fiancé, claiming he was an alcoholic, abusive to her and to their daughter, and that he used them "as props to promote his public image." Travis Barker, drummer for the bands Blink-182, 44, Box Car Racer and The Transplants and formerly of The Aquabats, proposed to Moakler in the elevator entrance to the Haunted Mansion ride at Disneyland.
Moakler made it to the semi-finals and finished seventh overall.
In 1995, Moakler was named Miss New York USA and represented New York in the Miss USA pageant, held that year in South Padre Island, Texas.
On the 120th episode of NBC's Minute to Win It (aka The Last Beauty Standing) which aired just before the 2010 Miss Universe contest on August 23, 2010, Moakler was the Last Beauty Standing among 10 contestants and was the top winner with 0,000 for her charity.Moakler has admitted that, even equipped with a ,000 Trek bike, she was somewhat accident-prone on the set, saying that when the cast had to "ride really close together for the camera" they would often "crash into each other like idiots and end up in a big ball of arms and legs." Moakler was a celebrity contestant on Search Party, a game show on the E! The show filmed at exotic beach resort locations and required contestants to team up for competitions such as athletic events and scavenger hunts.Moakler appeared in three episodes in 1999 to 2000.Barker paid off one of the ride operators so that the couple could have the space to themselves for a few minutes and then got down on one knee and proposed.Moakler said yes, but she later surprised Barker with her own down-on-one-knee proposal and engagement ring for him.