Aubrey O’Day went topless on Sept. 19 and it’s got Donald Trump Jr. in a wistful mood, HollywoodLife has EXCLUSIVELY learned. Uh oh, he’s dating Kimberly Guilfoyle!
Aubrey O’Day, 34, stripped to her tight jeans in the former Danity Kane member’s latest Instagram post on Sept. 18! Her alleged former lover, Donald Trump Jr., 40, definitely took notice, we’ve learned. Now, he’s wondering what could’ve been. Hey, eyes up here, Don — you’re a taken man! “Don thinks Aubrey looks smoking hot in her latest topless picture,” a D.C. insider EXCLUSIVELY shares with HollywoodLife. “He misses the chemistry they had together and regrets the bad timing they experienced.”
Aubrey and Don had an alleged affair in 2011 and 2012. This was before he filed for divorce in May of 2018 with Vanessa Trump, 40, although sources claimed Aubrey was told “DJT Jr.’s marriage was over” and that he “intended to leave his wife” before that, TMZ reported on Mar. 23. With their reported forbidden romance in the past, Don is now going steady with Kimberly Guilfoyle, 49. Their relationship is getting serious, but there’s no ring on Kimberly’s finger yet. “While he is really happy with Kimberly, if circumstances had been different, he would have loved to be with Aubrey instead,” our insider reveals. “He thinks Aubrey looks amazing and really sexy.”
We’re not going to challenge Aubrey’s sexiness. But — yikes! Don and Kimberly have been touring the country together nonstop. They showed up to Louisiana Attorney General Jeff Landry’s alligator hunt on Sept. 8, and fund-raised in the Hamptons on Aug. 24, where Kimberly said her and Don “make the perfect team” to Page Six. So, yeah, this is not a casual relationship. Well, Kimberly shouldn’t have to worry about more than a wandering eye, which Don reportedly seems privy to. Aubrey has zero feelings for the politician! “Aubrey is no longer a fan of Don. Jr. in any way,” a friend of Aubrey’s EXCLUSIVELY shared with us on Aug. 30. “Her crush on him is dead and done.”
And Don shouldn’t count on the singer’s vote, following buzz that Donald Trump’s son might succeed his dad in the 2024 presidential election. “If Don Jr. runs for president, one person that he will never be getting a vote from is Aubrey,” the same friend of Aubrey’s shared with us. “She feels very strongly that one Trump in the White House is enough. “