Aubrey O'Day has been long outspoken regarding her dislike for the Trump family. The 34-year-old singer first became intertwined with President Trump and his son Don Jr. when she appeared on Season 5 of reality television show The Apprentice in 2011. Despite Don Jr. being married to his wife Vanessa who was pregnant at the time, he and O'Day began a secret love affair, according to Us Weekly.
"Things started up with Aubrey and Don Jr. toward the end of the taping," a source close to O'Day said. The hidden relationship heated up quick, the two even reportedly considering having a child together. However, Don Jr. later ended the affair in 2012 after his wife found out about it when she stumbled across email exchanges between the pair. Vanessa eventually filed for divorce, their breakup causing a media frenzy of rumors and speculation. Since the unfortunate turn of events, O'Day has held a deep-rooted hatred for Don and his father. In November she even went so far as to post a picture of herself posing in front of the White House while holding up her middle finger.In an effort to mess with the president and his family, O'Day took a gig at Larry Flynt's Hustler Club in Las Vegas on New Year's Eve. The party was meant to honor Don Jr. who was turning 41-years-old. According to a video taken from inside the club, the singer seemed to enjoy the first part of the event. As her contract entailed, she gave a lively performance and mingled with guests. However, when a birthday cake for Don Jr. was rolled out, she quickly changed her tune.
After being asked to sing "Happy Birthday" to her ex-boyfriend, O'Day refused and was quickly kicked out of the club. Video obtained from the evening shows multiple security guards escorting the singer out of the Las Vegas club after swearing at her and accusing her of breaking her professional contract.
Don Trump Jr. did not comment on O'Day's actions. He posted an Instagram photo of himself enjoying the evening with his girlfriend, Kimberly Guilfoyle, a former Fox News host.
Don Jr. shares five children with his ex-wife Vanessa including Kai, 11; Donald Trump III, 9; Tristan, 7; Spencer, 6; and Chloe, 4. The pair remain on cordial terms for the sake of their children. Following the announcement of their divorce in 2018, they shared a joint statement saying that they will "always have tremendous respect for each other."