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Aubrey O’Day’s History of Cryptic References To an Affair With Someone Who Might Be Donald Trump Jr.

Aubrey O'Day Hints at Affair With Married Man

On March 19, just four days after Donald Trump Jr.’s wife Vanessa filed divorce papers, gossip blogger Perez Hilton reported that the president’s son carried on an affair with former Danity Kane singer Aubrey O’Day after the two met while filming the 5th season of Celebrity Apprentice in the fall of 2011. US Weekly later added its own sourcing, estimating that the alleged affair began at the end of 2011 and carried on until March 2012, when Vanessa was pregnant with the third of the pair’s five children.

In the days since Hilton reported the rumor, the internet has scrutinized O’Day’s lyrics, interviews, and social media accounts with Zapruder-like intensity. Here are all the ephemera that might or might not refer to the president’s oldest son.

In October 2011, the fifth season of Celebrity Apprentice began filming. O’Day—along with co-stars Dee Snider, Debbie Gibson, and Victoria Gotti—is spotted filming for Donald Trump’s former reality show. The show would air beginning in February 2012. O’Day was fired from the show along with comedian Lisa Lampanelli in its third to last episode, with Trump Jr. serving as judge. Arsenio Hall eventually won the season, beating out Clay Aiken.

March 24, 2012 — O’Day posts a photo of an unnamed man’s feet covering her feet while the two laid in bed.

The Daily Mail‘s dug up a 2012 tweet posted by O’Day showing her and a mystery man playing footsie in bed. The Mail even went as far as tracking down barefoot photos of Don Jr. feet for comparison. While they do look similar, all dudes’ feet look like gnarled monkey paws.

On Wednesday, US Weekly ran a story with sources claiming that in 2012 Vanessa called O’Day after discovering the affair and confronted her in a phone call.“She called Aubrey with her kids on the phone,” a source said. Another person close to the situation told the magazine, “Vanessa went crazy and was super jealous.”

US Weekly’s report coincides with a People story claiming that Vanessa confronted her husband about the affair after she discovered “sexy texts” on his phone while he was in the shower.“This is how Vanessa found out and the affair ended,” a source who “worked with Celebrity Apprentice” told People. “To Don Jr. [the affair] was very exciting. Aubrey was very, very into Don. He liked her but she was definitely more keen on him.”

July, 2012 — O’Day uploads a Gotye cover to YouTube about an affair with a married man. 

O’Day channeled heartbreak into her music when she recorded a version of Gotye’s “Somebody That I Used to Know” where she changed the lyrics to explicitly depict heartbreak from an ill-fated affair with a married man.

TMZ obtained footage of an unfinished video O’Day recorded of her Gotye cover in 2012, after the alleged affair is said to have ended. In the video, a topless O’Day makes use of a reliable trope of writing words like “cheater,” “affair,” and “hate” on her naked body.


December, 2012 — O’Day discusses an affair with a “reality star” during the live show of a storytelling podcast.

That same year, O’Day discussed a relationship with “a reality star” in a live-storytelling event for the RISK! podcast.

From Page Six:

O’Day told the podcast “RISK!’’ that she was once “filming a show and started up this unspoken connection with a big celebrity who I can’t name ’cause I’ll get sued up the a–.”

O’Day said that after shooting a “big performance,’’ she and the celebrity launched into a sex session in the bathroom — “all over, on top of this, under this, beneath this.’’

She said their affair continued, even though “we’re from different worlds.’’ It ended when she caught him in his New York apartment with a naked woman.”

It’s worth noting that Celebrity Apprentice is far from the first reality show upon which O’Day appeared. O’Day got her start as a singer on Diddy’s MTV show Making the Band 3. She also popped up on Keeping up with the Kardashians in 2009 and RuPaul’s Drag Race in 2013. She also met ex-boyfriend Paul “Pauly D” DelVecchio of MTV’s Jersey Shore fame on the E! relationship show Famously Single.

August, 2013 — O’Day releases Between Two Evils EP featuring a breakup song titled “DJT.”

The closest O’Day came to exposing the alleged affair appeared to occur in 2013 when she released a single titled “DJT,” which sounds like an angry fuck you from a jilted lover. DJT, of course, are also Don Jr.’s initials.

November 2016 — O’Day tweets on Election Night that her story is now “worth millions.”

O’Day was feeling a certain way on Election Night when she tweeted: “My story I didn’t tell is worth millions now 😉 … this doesn’t hurt me, it hurts America” at someone responding to a tweet where she wrote that she was “embarrassed to be an American.” The tweets have since been deleted and she never elaborated on what that lucrative story might entail.

Spin reached out to O’Day to see if she would be willing to comment on the nature of her relationship with Don Jr. during and after the filming Celebrity Apprentice and asked if “DJT” was indeed about him, but we did not hear back. Two days ago, Page Six reached out to Don Jr. for comment on reports of an alleged extra-marital relationship with O’Day. From Page Six:

Trump Jr., reached by phone by The Post, chuckled when asked if he’d like to comment and then said, “No’’ before hanging up.

The president’s son and the Danity Kane singer may very well have never hooked up. Or maybe they did. So far, neither of them is saying a word, though O’Day appears to have been far from quiet in the past.