Jessica Simpson Named In 20-Year-Old Grudge Over A Dream

Jessica Simpson‘s romantic wish for Dale Earnhardt landed her a spot in his wife’s bad books!

The American race driver’s wife recalled how a fangirling moment over the singer turned into her literally marking territory over his heart.

Jessica Simpson did not end up marrying Dale Earnhardt, but she gave marriage a shot two different times, which unfortunately did not work out.

Amy claimed the 20-year beef (mostly one-sided) with Simpson began when she was dying to meet the singer in 2008/2009. She recalled that while she was visiting Dale at the Daytona International Speedway in Florida, she had told her then-boyfriend, now-husband, Dale, to introduce them.

The race driver, however, advised against it and went ahead to play her a video of the singer revealing in an interview that she dreamt that she and Dale got married in a treehouse.

Amy, who had felt drawn to Simpson due to their Texan roots and age bracket, immediately drew a line and decided not see the singer or buy anything she was selling. According to her, on the latest episode of her “Bless Your ‘Hardt” podcast:

“I was like, She was f-cking trying to fish my man! She knew exactly what she was doing. She heard that you wanted to build a tree house and she’s like, ‘I had a dream! We’re meant to be together.'”

Simpson did not hit it off with Dale, but she found a fiery romance with her estranged husband, Nick Lachey, after they met on tour in 1999.

As noted by Page Six, Simpson and Lachey got married three years later and introduced the world to their life behind the scenes in their reality show on MTV, which ran for just three seasons.

Unfortunately, the couple split in 2005 and finalized their divorce in 2006, after which Simpson reportedly moved on with Adam Levine, but the relationship did not work out.

The singer once again found love with John Mayer in 2006, but she revealed in her memoir that they went round in circles in the toxic relationship and broke up nine times.

Simpson turned her interest to the NFL and hit the bull’s eye with Tony Romo in 2007, but that romance barely lasted two years before the athlete reportedly dumped Simpson on the eve of her 29th birthday.

The fashion designer then began dating her second husband, Eric Johnson, in 2010 while he wrapped up his divorce from Keri D’Angelo.

Simpson and Johnson got married in 2014 and welcomed three children together. They announced their separation 11 years later in 2025, with the actress revealing that they had been living separately, but focusing on their kids.

Like the media personality explained in her statement, things have remained cordial between her and Johnson as they navigate their split. Interestingly, The Blast shared that speculations have emerged that the silence from their quarters may be an indication of a reconciliation.

Simpson’s father, Joe, waded into the situation, refusing to confirm or deny these reports, while stating that the choice is ultimately the singer and Johnson’s to make. 

He, however, affirmed that his ex-son-in-law will forever remain a part of the family despite the uncertainty surrounding his marriage to her daughter.

Joe noted that Johnson was welcome to spend Christmas with the family, after he enjoyed a lovely Thanksgiving holiday with the fashion designer and their children.

Simpson did not let her failed marriage taint her thoughts on love; if anything, the singer is ready to go into the dating world with more caution. According to her, the dating terrain has changed over the years into a more vicious space, and she can only trust to find love through a more traditional route, where the introduction is done manually.

Simpson emphasized that she would not mind getting set up by a friend to find the new love of her life. The TV star reinforced her stance when she shut down reports of her appearing on “The Bachelorette” to find love.