Dale Jr. Roasts Tony Stewart Over Shocking Engagement To Playboy Model

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In a move that took his fans by complete surprise, NASCAR star Tony Stewart revealed on Saturday, November 23rd, that he had proposed to his girlfriend – and she said “yes!”

Not only were his fans taken by surprise, but fellow drivers and industry professionals like Dale Earnhardt Jr. were also caught off guard! Taking to social media, this longtime friend of Stewart’s and NASCAR’s 14-time most-popular driver ribbed him about the engagement with a few hysterical tweets.

Stewart, who has been dating former Playboy Playmate Pennelope Jimenez since his retirement from the sport after the 2016 season, shared a photo of her hand adorned with a massive engagement ring paired with the caption, “She said YES!”

Jimenez was named Miss March 2003 for her work with Playboy and has since appeared in a variety of television commercials and other film projects.

Taking note of Stewart’s newfound passion for fitness and biking, Dale Jr. took the announcement as an opportunity to poke fun at his friend, who suggested in September that he may remain a bachelor forever!

Check out Tony Stewart’s interview with Dan Patrick where he talks about his close friend, Dale Jr., in the video below and let us know what you think of Dale Jr.’s roasting Tony in the comments!