Aubrey O'Day's Dating History in 12 Clicks: From Her Rumored Affair With Donald Trump Jr. to Her Romance With Pauly D and More

Aubrey O'Day's first known relationship was with DJ Cassidy in 2006.

"He's in the industry himself, so he's very supportive of me," she told AOL Music of her boyfriend at the time.

She also attended his 25th birthday party at The Plumm in New York City, but their relationship seemingly ended afterward.

Years after O'Day debuted in Danity Kane, she sparked dating rumors with Bad Boy Records founder Sean "Diddy" Combs. However, both denied the buzz.

The former girl group member has since accused her former mentor of trying to buy her silence and asking her to sign an NDA.

The document, which she and her former bandmates did not take, encouraged them to never disparage Combs and his label.

"There's no vindication when you're a victim of someone. ... Anyone being exposed, or any truths being told, don't change the reality of what you experienced," she told People amid the embattled rap mogul's legal headaches.

"It's a forever thing that you have to wake up every day and choose to evolve past. It doesn't go away," she continued. "It's like childhood trauma. We don't like to think it just disappears in our thirties, but really we start realizing how bad it really is in our thirties."

In 2007, O'Day reportedly dated Evan Ross for three months before calling it quits for good. They never spoke about their past relationship.

On the other hand, Ross moved on with Ashlee Simpson and married her in 2014. They have two children together.

O'Day confirmed to OK! in 2008 that she was dating Quddus, though she clarified he was "in a trial period."

“I’ve been heartbroken too many times to fall into it anymore," the Making the Band 3 alum shared. "Everybody gets a trial period until I know it’s a good thing. I’m seeing if he’ll work out.”

They met at a Danity Kane album release party in March of the same year and had several dates afterward.

She also applauded Quddus for being "incredibly witty, intelligent and very patient" at the time, adding she needed a man "who is patient because Lord knows I am one big drama after another.”

After O'Day's brief relationship with Quddus, she was spotted making out with Jesse McCartney.

However, the "Beautiful Soul" hitmaker clarified the buzz during an interview with Ryan Seacrest.

"We had a big show in New York, and then I think just a bunch of my friends, a bunch of her friends — we all went out together, but it never really amounted to anything," McCartney said after admitting he and O'Day truly "hung out one night."

O'Day was also linked to her "BFF" Jenna Jameson in 2008. They also kissed when they attended Perez Hilton's Blue Ball Birthday Celebration.

Making the Band 4 briefly documented O'Day's relationship with Donnie Klang. Their on-again, off-again romance in 2008 appeared to have ended as quickly as it started.

When Donnie Wahlberg's marriage to Kimberly Fey hit rock bottom, tabloids claimed the "Wrecking Ball" singer entered the picture and started spending time with The Wahlbergs star.

The pair also attended the premiere of Righteous Kill, fueling speculation that they were indeed a couple.

The "Love Me When You Leave" singer surprised the viewers of Ex on the Beach when she called Donald Trump Jr. her ex after referring to him as her soulmate. They reportedly had an affair in 2012, though it ended after Don Jr.'s then-wife, Vanessa Trump, discovered their text exchange.

Even Donald Trump reportedly knew about the entanglement.

"When I ask Trump about O’Day’s affair with Don Jr., he takes a long pause. 'I had heard that, actually,' he says, blinking. 'No, I had heard that.' Did he know that O’Day had written a song about Don Jr.? 'I hadn’t heard the song. But I had heard that,' Trump says, confirming once again that he’s aware of the story about Don Jr. sleeping with one of the contestants on The Celebrity Apprentice," an excerpt from Ramin Setoodeh's book Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass, read.

O'Day also had an on-again, off-again relationship with Travis Garland in 2015 before calling it quits for good after a season of Marriage Boot Camp: Reality Stars.

"It's probably the hardest relationship I've been in, in regards to the dynamics," said O'Day. "You know, we always find our way, we always find it."

In 2016, O'Day met Pauly D while filming Famously Single. They also had a tumultuous relationship before breaking up for good in July 2017.